Structure

Physi-Chem Properties

Molecular Weight:  470.19
Volume:  455.496
LogP:  2.489
LogD:  1.612
LogS:  -4.988
# Rotatable Bonds:  1
TPSA:  104.57
# H-Bond Aceptor:  8
# H-Bond Donor:  0
# Rings:  7
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.455
Synthetic Accessibility Score:  6.074
Fsp3:  0.731
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.369
MDCK Permeability:  2.038608363363892e-05
Pgp-inhibitor:  0.984
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.906
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.84
Plasma Protein Binding (PPB):  71.8366470336914%
Volume Distribution (VD):  0.922
Pgp-substrate:  26.661216735839844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.204
CYP2C19-inhibitor:  0.107
CYP2C19-substrate:  0.587
CYP2C9-inhibitor:  0.173
CYP2C9-substrate:  0.014
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.674
CYP3A4-substrate:  0.467

ADMET: Excretion

Clearance (CL):  9.568
Half-life (T1/2):  0.772

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.193
Drug-inuced Liver Injury (DILI):  0.355
AMES Toxicity:  0.088
Rat Oral Acute Toxicity:  0.968
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.181
Carcinogencity:  0.377
Eye Corrosion:  0.031
Eye Irritation:  0.565
Respiratory Toxicity:  0.953

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC305016

Natural Product ID:  NPC305016
Common Name*:   Limonin
IUPAC Name:   n.a.
Synonyms:   Limonin
Standard InCHIKey:  KBDSLGBFQAGHBE-MSGMIQHVSA-N
Standard InCHI:  InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
SMILES:  O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL517449
PubChem CID:   179651
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids
          • [CHEMONTID:0002380] Limonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88710-5]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10096857]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota Root barks n.a. n.a. PMID[11473427]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota Leaves n.a. n.a. PMID[14510598]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[15128261]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota Leaves n.a. n.a. PMID[17637068]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[17666859]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17689080]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota root bark n.a. n.a. PMID[18198838]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[18302336]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota leaves n.a. n.a. PMID[18357995]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[18950230]
NPO24475 Aceriphyllum rossii n.a. n.a. n.a. n.a. n.a. n.a. PMID[19618898]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22432912]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23186307]
NPO23805 Arnica nevadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23507152]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[25522543]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25919052]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[26724423]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[26724423]
NPO7171 Salvia polystachya Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29135252]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31836445]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7176 Citrus sudachii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28170 Thalictrum incidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO547 Thalictrum lucidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31304 Mahonia repens n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7815 Berberis tschonoskiana Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27082 Citrus yuko Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7371 Citrus tangemna Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27693 Dehaasia triandra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30082 Evodia meliifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29208 Dictamnus albus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6001 Fructus evodiae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29208 Dictamnus albus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28170 Thalictrum incidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6001 Fructus evodiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7171 Salvia polystachya Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7176 Citrus sudachii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7815 Berberis tschonoskiana Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27693 Dehaasia triandra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27082 Citrus yuko Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7371 Citrus tangemna Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17959 Berberis repens Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO547 Thalictrum lucidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO547 Thalictrum lucidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29208 Dictamnus albus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25529 Bursaria spinosa Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1329 Esenbeckia hartmanii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23805 Arnica nevadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25699 Vitex madiensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16000 Cetorhinus maximus Species Alopiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7966 Grewia villosa Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29208 Dictamnus albus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25390 Pterocarpus grandiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23567 Coccus fagi Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24675 Quercus aegilops Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25326 Dendrosenecio kilimanjari Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25090 Araujia sericifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7552 Alligator mississippiensis Species Alligatoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25291 Lactarius scrobiculatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21284 Cynoglossum viridiflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13941 Aeollanthus buchnerianus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18014 Gracilaria eucheumoides Species Gracilariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28665 Sesbania punicea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24218 Fusarium gibbosum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26128 Clonostachys rosea Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17231 Pycnarrhena australiana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25187 Cladonia evansii Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20279 Parmelia damaziana Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24640 Echinops amplexicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23691 Pyrosoma giganteum Species Pyrosomatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24599 Streptomyces althioticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1109 Corydalis persica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24987 Simira eliezeriana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16406 Leptospermum recurvum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7445 Pteris prolifera Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24291 Rhizobium phaseoli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17624 Spatoglossum pacificum Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16936 Evea brasiliensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25234 Epaltes gariepina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12658 Melipotis perpendicularis Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27082 Citrus yuko Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20833 Beyeria brevifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24929 Aria pallescens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11784 Sickingia rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23963 Odixia angusta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24068 Prunus laurocerasus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17959 Berberis repens Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24830 Prosopis glandulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24475 Aceriphyllum rossii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11119 Salta triflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11475 Vernonia chloropappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25471 Chromolaena pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24511 Dipterocarpus alatus Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18352 Anaxagorea clavata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27693 Dehaasia triandra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26042 Agnorhiza bolanderi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25671 Gardenia fosbergii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5451 Ageratina saltillensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23453 Pheidole pallidula Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1794 Ilex affinis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20823 Stenostomum lucidum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3560 Trifolium montanum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14640 Uresiphita reversalis Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25144 Artemisia monogyna Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24383 Ficus formosana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7171 Salvia polystachya Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO547 Thalictrum lucidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5799 Streptomyces chryseus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24556 Bassia butyracea Species Abylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[559849]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 0.00423 ug.mL-1 PMID[559854]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 0.00211 ug.mL-1 PMID[559854]
NPT927 Cell Line PBMC Homo sapiens CC50 = 451.91 ug.mL-1 PMID[559854]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Ki = 23200.0 nM PMID[559855]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Kinact = 0.266 min-1 PMID[559855]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -0.85 % PMID[559856]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4300.0 nM PMID[559867]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 26000.0 nM PMID[559867]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 9439.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 2683.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 10590.9 nM PubChem BioAssay data set
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 18.0 nM PMID[559848]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Emax = 75.9 % PMID[559848]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 100.0 ug.mL-1 PMID[559850]
NPT92 Individual Protein Serotonin 1a (5-HT1a) receptor Homo sapiens Ki > 100000.0 nM PMID[559851]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 3.6 % PMID[559852]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 26100.0 nM PMID[559853]
NPT2 Others Unspecified IC50 = 38200.0 nM PMID[559853]
NPT2 Others Unspecified Ratio CC50/IC50 = 450.0 n.a. PMID[559854]
NPT2 Others Unspecified Ratio IC50 = 1000.0 n.a. PMID[559854]
NPT2 Others Unspecified IC50 = 0.00031 ug.mL-1 PMID[559854]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 0.92 ug.mL-1 PMID[559854]
NPT3954 Organism Human T-lymphotropic virus 1 Human T-lymphotropic virus 1 IC50 = 1.07 ug.mL-1 PMID[559854]
NPT27 Others Unspecified Ratio = 62.0 n.a. PMID[559854]
NPT27 Others Unspecified Ratio = 33.0 n.a. PMID[559854]
NPT27 Others Unspecified Ratio = 10.0 n.a. PMID[559854]
NPT27 Others Unspecified CC50 = 201.56 ug.mL-1 PMID[559854]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -14.07 % PMID[559856]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda AFI = 87.0 % PMID[559857]
NPT1848 Organism Puccinia arachidis Puccinia arachidis Inhibition = -15.7 % PMID[559858]
NPT1848 Organism Puccinia arachidis Puccinia arachidis Inhibition = 67.7 % PMID[559858]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 102.17 % PMID[559859]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 92.09 % PMID[559859]
NPT35 Others n.a. Solubility < 5.0 ug.mL-1 PMID[559860]
NPT32 Organism Mus musculus Mus musculus Inhibition = 45.91 % PMID[559860]
NPT32 Organism Mus musculus Mus musculus Activity = 89.3 % PMID[559860]
NPT32 Organism Mus musculus Mus musculus Inhibition = 32.74 % PMID[559860]
NPT2 Others Unspecified AC50 n.a. 631.0 nM PMID[559861]
NPT2 Others Unspecified Ac50 n.a. 0.631 uM PMID[559861]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -1.4 % PMID[559862]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens IC50 = 19140.0 nM PMID[559863]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -1.96 % PMID[559864]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.15 % PMID[559865]
NPT32 Organism Mus musculus Mus musculus Inhibition = 14.42 % PMID[559866]
NPT32 Organism Mus musculus Mus musculus Inhibition = 44.2 % PMID[559866]
NPT32 Organism Mus musculus Mus musculus Inhibition = 39.71 % PMID[559866]
NPT32 Organism Mus musculus Mus musculus Inhibition = 26.32 % PMID[559866]
NPT32 Organism Mus musculus Mus musculus Inhibition = 22.0 % PMID[559866]
NPT32 Organism Mus musculus Mus musculus Inhibition = 57.28 % PMID[559866]
NPT2 Others Unspecified IC50 = 42000.0 nM PMID[559867]
NPT2 Others Unspecified Potency n.a. 13333.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5308 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8485.2 nM PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC305016 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9669 High Similarity NPC60973
0.9548 High Similarity NPC123088
0.9545 High Similarity NPC470939
0.9542 High Similarity NPC237155
0.9539 High Similarity NPC263265
0.9481 High Similarity NPC25255
0.9477 High Similarity NPC286722
0.9427 High Similarity NPC476850
0.9427 High Similarity NPC476861
0.9419 High Similarity NPC193798
0.9416 High Similarity NPC473473
0.9416 High Similarity NPC475295
0.9412 High Similarity NPC107646
0.9412 High Similarity NPC209364
0.9359 High Similarity NPC469846
0.9355 High Similarity NPC475381
0.9351 High Similarity NPC472283
0.9304 High Similarity NPC473753
0.9304 High Similarity NPC473766
0.9299 High Similarity NPC476857
0.9299 High Similarity NPC476858
0.9299 High Similarity NPC476860
0.9299 High Similarity NPC476856
0.9295 High Similarity NPC117986
0.9286 High Similarity NPC126723
0.9241 High Similarity NPC23387
0.9236 High Similarity NPC477405
0.9231 High Similarity NPC191828
0.9221 High Similarity NPC469850
0.9211 High Similarity NPC196864
0.9211 High Similarity NPC477404
0.9182 High Similarity NPC472282
0.9182 High Similarity NPC476853
0.9182 High Similarity NPC173516
0.9172 High Similarity NPC5079
0.9167 High Similarity NPC477403
0.9167 High Similarity NPC473368
0.915 High Similarity NPC18135
0.9139 High Similarity NPC221809
0.9125 High Similarity NPC160651
0.9125 High Similarity NPC271235
0.9125 High Similarity NPC471397
0.9114 High Similarity NPC39986
0.9114 High Similarity NPC234660
0.9114 High Similarity NPC476197
0.9114 High Similarity NPC302369
0.9114 High Similarity NPC51568
0.9114 High Similarity NPC292389
0.9114 High Similarity NPC469338
0.9114 High Similarity NPC134254
0.9108 High Similarity NPC472653
0.9108 High Similarity NPC335761
0.9091 High Similarity NPC75906
0.9091 High Similarity NPC476201
0.9085 High Similarity NPC159927
0.9085 High Similarity NPC469335
0.9085 High Similarity NPC46551
0.9073 High Similarity NPC262198
0.9062 High Similarity NPC472651
0.9057 High Similarity NPC469849
0.9057 High Similarity NPC276551
0.9057 High Similarity NPC470940
0.9051 High Similarity NPC69028
0.9051 High Similarity NPC263432
0.9051 High Similarity NPC82851
0.9006 High Similarity NPC472652
0.9 High Similarity NPC470875
0.8994 High Similarity NPC419
0.8987 High Similarity NPC477402
0.8981 High Similarity NPC299038
0.8981 High Similarity NPC167142
0.8981 High Similarity NPC249021
0.8981 High Similarity NPC187149
0.8974 High Similarity NPC44675
0.8974 High Similarity NPC214541
0.8974 High Similarity NPC476262
0.8961 High Similarity NPC476122
0.8957 High Similarity NPC469848
0.894 High Similarity NPC86935
0.8938 High Similarity NPC271657
0.8931 High Similarity NPC149896
0.8931 High Similarity NPC18347
0.8931 High Similarity NPC329938
0.8931 High Similarity NPC96443
0.8931 High Similarity NPC290400
0.8931 High Similarity NPC197596
0.8924 High Similarity NPC475967
0.8889 High Similarity NPC470941
0.8861 High Similarity NPC45101
0.8861 High Similarity NPC261597
0.8861 High Similarity NPC36655
0.8854 High Similarity NPC264943
0.8854 High Similarity NPC469336
0.8834 High Similarity NPC302392
0.8834 High Similarity NPC82602
0.8827 High Similarity NPC472774
0.8827 High Similarity NPC472775
0.8812 High Similarity NPC472771
0.8797 High Similarity NPC469485
0.879 High Similarity NPC57998
0.879 High Similarity NPC178932
0.879 High Similarity NPC282445
0.878 High Similarity NPC159232
0.878 High Similarity NPC160818
0.878 High Similarity NPC169299
0.8758 High Similarity NPC471168
0.8758 High Similarity NPC472773
0.8742 High Similarity NPC472772
0.8742 High Similarity NPC173544
0.8734 High Similarity NPC281258
0.8726 High Similarity NPC44577
0.8712 High Similarity NPC476224
0.8696 High Similarity NPC471167
0.8696 High Similarity NPC207978
0.8696 High Similarity NPC471166
0.8696 High Similarity NPC200782
0.8696 High Similarity NPC6326
0.8693 High Similarity NPC142113
0.8667 High Similarity NPC476943
0.865 High Similarity NPC475779
0.8642 High Similarity NPC224394
0.8642 High Similarity NPC663
0.8623 High Similarity NPC262386
0.8608 High Similarity NPC268905
0.8608 High Similarity NPC469503
0.8606 High Similarity NPC470995
0.8599 High Similarity NPC156189
0.8589 High Similarity NPC470182
0.8581 High Similarity NPC346
0.858 High Similarity NPC472668
0.8571 High Similarity NPC307383
0.8571 High Similarity NPC478177
0.8571 High Similarity NPC472665
0.8563 High Similarity NPC471437
0.8562 High Similarity NPC204663
0.8554 High Similarity NPC285227
0.8545 High Similarity NPC327922
0.8544 High Similarity NPC116717
0.8538 High Similarity NPC105395
0.8538 High Similarity NPC247563
0.8538 High Similarity NPC242068
0.8537 High Similarity NPC478178
0.8535 High Similarity NPC195325
0.8528 High Similarity NPC476035
0.8528 High Similarity NPC14499
0.8528 High Similarity NPC475039
0.8528 High Similarity NPC472669
0.8526 High Similarity NPC250228
0.8512 High Similarity NPC167340
0.8509 High Similarity NPC195131
0.8509 High Similarity NPC469847
0.8506 High Similarity NPC267632
0.8506 High Similarity NPC223415
0.8506 High Similarity NPC470741
0.8497 Intermediate Similarity NPC20500
0.8485 Intermediate Similarity NPC100333
0.8477 Intermediate Similarity NPC310830
0.8476 Intermediate Similarity NPC472664
0.8476 Intermediate Similarity NPC146991
0.8471 Intermediate Similarity NPC19747
0.8466 Intermediate Similarity NPC211777
0.8457 Intermediate Similarity NPC474932
0.8457 Intermediate Similarity NPC262872
0.8452 Intermediate Similarity NPC236004
0.8452 Intermediate Similarity NPC251865
0.8442 Intermediate Similarity NPC473152
0.8438 Intermediate Similarity NPC30222
0.8424 Intermediate Similarity NPC97574
0.8424 Intermediate Similarity NPC149945
0.8424 Intermediate Similarity NPC93172
0.8424 Intermediate Similarity NPC472141
0.8424 Intermediate Similarity NPC214600
0.8424 Intermediate Similarity NPC121995
0.8421 Intermediate Similarity NPC220094
0.8418 Intermediate Similarity NPC470790
0.8418 Intermediate Similarity NPC471001
0.8418 Intermediate Similarity NPC470791
0.8415 Intermediate Similarity NPC198047
0.8415 Intermediate Similarity NPC285567
0.8415 Intermediate Similarity NPC472139
0.8405 Intermediate Similarity NPC333139
0.8405 Intermediate Similarity NPC287559
0.8405 Intermediate Similarity NPC470789
0.8395 Intermediate Similarity NPC472777
0.8395 Intermediate Similarity NPC472776
0.8395 Intermediate Similarity NPC472778
0.8385 Intermediate Similarity NPC35000
0.8385 Intermediate Similarity NPC75310
0.8373 Intermediate Similarity NPC478179
0.8373 Intermediate Similarity NPC472764
0.8365 Intermediate Similarity NPC5180
0.8354 Intermediate Similarity NPC18986
0.8354 Intermediate Similarity NPC472767
0.8354 Intermediate Similarity NPC188649
0.8353 Intermediate Similarity NPC470181
0.8344 Intermediate Similarity NPC475226
0.8343 Intermediate Similarity NPC94763
0.8333 Intermediate Similarity NPC104736
0.8333 Intermediate Similarity NPC476944
0.8323 Intermediate Similarity NPC472765

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC305016 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8405 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD5760 Phase 2
0.8049 Intermediate Similarity NPD5761 Phase 2
0.7955 Intermediate Similarity NPD8434 Phase 2
0.767 Intermediate Similarity NPD6764 Approved
0.767 Intermediate Similarity NPD6765 Approved
0.75 Intermediate Similarity NPD6784 Approved
0.75 Intermediate Similarity NPD6785 Approved
0.7399 Intermediate Similarity NPD5494 Approved
0.7346 Intermediate Similarity NPD1471 Phase 3
0.7337 Intermediate Similarity NPD6599 Discontinued
0.731 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7075 Discontinued
0.7257 Intermediate Similarity NPD1247 Approved
0.7241 Intermediate Similarity NPD919 Approved
0.7168 Intermediate Similarity NPD5402 Approved
0.716 Intermediate Similarity NPD920 Approved
0.7151 Intermediate Similarity NPD6801 Discontinued
0.711 Intermediate Similarity NPD7819 Suspended
0.7093 Intermediate Similarity NPD7411 Suspended
0.7088 Intermediate Similarity NPD6559 Discontinued
0.7083 Intermediate Similarity NPD6799 Approved
0.7076 Intermediate Similarity NPD3226 Approved
0.7069 Intermediate Similarity NPD3817 Phase 2
0.7059 Intermediate Similarity NPD5403 Approved
0.7041 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5401 Approved
0.7027 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4628 Phase 3
0.6989 Remote Similarity NPD3749 Approved
0.6979 Remote Similarity NPD8285 Discontinued
0.6971 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6923 Remote Similarity NPD643 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8313 Approved
0.6919 Remote Similarity NPD8312 Approved
0.6889 Remote Similarity NPD3926 Phase 2
0.6868 Remote Similarity NPD3751 Discontinued
0.6868 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6868 Remote Similarity NPD7799 Discontinued
0.6867 Remote Similarity NPD2796 Approved
0.6851 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6851 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6851 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6851 Remote Similarity NPD6166 Phase 2
0.6847 Remote Similarity NPD8404 Phase 2
0.6845 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4380 Phase 2
0.6836 Remote Similarity NPD3882 Suspended
0.6836 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6833 Remote Similarity NPD3787 Discontinued
0.6831 Remote Similarity NPD5844 Phase 1
0.6826 Remote Similarity NPD2346 Discontinued
0.6809 Remote Similarity NPD8150 Discontinued
0.6798 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6959 Discontinued
0.6774 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6769 Remote Similarity NPD4107 Approved
0.6757 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6797 Phase 2
0.6746 Remote Similarity NPD1243 Approved
0.6744 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6728 Remote Similarity NPD6832 Phase 2
0.6725 Remote Similarity NPD7236 Approved
0.6723 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7473 Discontinued
0.672 Remote Similarity NPD7251 Discontinued
0.6707 Remote Similarity NPD3748 Approved
0.6706 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6273 Approved
0.6686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3818 Discontinued
0.6685 Remote Similarity NPD8127 Discontinued
0.6684 Remote Similarity NPD7808 Phase 3
0.6667 Remote Similarity NPD1934 Approved
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD3887 Approved
0.6667 Remote Similarity NPD2403 Approved
0.6667 Remote Similarity NPD6980 Clinical (unspecified phase)
0.665 Remote Similarity NPD4482 Phase 3
0.6648 Remote Similarity NPD4965 Approved
0.6648 Remote Similarity NPD6808 Phase 2
0.6648 Remote Similarity NPD6232 Discontinued
0.6648 Remote Similarity NPD4966 Approved
0.6648 Remote Similarity NPD4967 Phase 2
0.6647 Remote Similarity NPD2534 Approved
0.6647 Remote Similarity NPD2532 Approved
0.6647 Remote Similarity NPD2533 Approved
0.6646 Remote Similarity NPD3267 Approved
0.6646 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3266 Approved
0.6629 Remote Similarity NPD7239 Suspended
0.6613 Remote Similarity NPD7074 Phase 3
0.6612 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6607 Remote Similarity NPD2799 Discontinued
0.6595 Remote Similarity NPD7228 Approved
0.6591 Remote Similarity NPD7458 Discontinued
0.6588 Remote Similarity NPD1549 Phase 2
0.6576 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6234 Discontinued
0.6571 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6568 Remote Similarity NPD6099 Approved
0.6568 Remote Similarity NPD1551 Phase 2
0.6568 Remote Similarity NPD6100 Approved
0.6559 Remote Similarity NPD7054 Approved
0.6552 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6545 Remote Similarity NPD2313 Discontinued
0.6545 Remote Similarity NPD3268 Approved
0.6543 Remote Similarity NPD7685 Pre-registration
0.6536 Remote Similarity NPD1465 Phase 2
0.6529 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6529 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6527 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6527 Remote Similarity NPD6355 Discontinued
0.6527 Remote Similarity NPD1933 Approved
0.6526 Remote Similarity NPD8407 Phase 2
0.6524 Remote Similarity NPD7472 Approved
0.6517 Remote Similarity NPD5889 Approved
0.6517 Remote Similarity NPD5890 Approved
0.6515 Remote Similarity NPD6777 Approved
0.6515 Remote Similarity NPD6782 Approved
0.6515 Remote Similarity NPD6778 Approved
0.6515 Remote Similarity NPD6779 Approved
0.6515 Remote Similarity NPD6781 Approved
0.6515 Remote Similarity NPD6776 Approved
0.6515 Remote Similarity NPD6780 Approved
0.6512 Remote Similarity NPD3750 Approved
0.6509 Remote Similarity NPD7033 Discontinued
0.65 Remote Similarity NPD7696 Phase 3
0.65 Remote Similarity NPD7698 Approved
0.65 Remote Similarity NPD7697 Approved
0.65 Remote Similarity NPD1547 Clinical (unspecified phase)
0.648 Remote Similarity NPD37 Approved
0.6478 Remote Similarity NPD17 Approved
0.6476 Remote Similarity NPD7907 Approved
0.6471 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7874 Approved
0.6468 Remote Similarity NPD8320 Phase 1
0.6468 Remote Similarity NPD8319 Approved
0.6467 Remote Similarity NPD4307 Phase 2
0.6467 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6464 Remote Similarity NPD7768 Phase 2
0.6461 Remote Similarity NPD6585 Discontinued
0.6459 Remote Similarity NPD4111 Phase 1
0.6455 Remote Similarity NPD8368 Discontinued
0.6455 Remote Similarity NPD7240 Approved
0.6453 Remote Similarity NPD2800 Approved
0.6444 Remote Similarity NPD2801 Approved
0.6433 Remote Similarity NPD2353 Approved
0.6433 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6433 Remote Similarity NPD5763 Approved
0.6433 Remote Similarity NPD5762 Approved
0.6433 Remote Similarity NPD2344 Approved
0.642 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6413 Remote Similarity NPD7199 Phase 2
0.6409 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6407 Remote Similarity NPD8032 Phase 2
0.6395 Remote Similarity NPD2897 Discontinued
0.6395 Remote Similarity NPD970 Clinical (unspecified phase)
0.6392 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6386 Remote Similarity NPD7870 Phase 2
0.6386 Remote Similarity NPD7871 Phase 2
0.6381 Remote Similarity NPD4665 Approved
0.6374 Remote Similarity NPD2935 Discontinued
0.6374 Remote Similarity NPD2438 Suspended
0.6374 Remote Similarity NPD7057 Phase 3
0.6374 Remote Similarity NPD7058 Phase 2
0.6373 Remote Similarity NPD7701 Phase 2
0.6368 Remote Similarity NPD3057 Approved
0.6364 Remote Similarity NPD5980 Discovery
0.6358 Remote Similarity NPD3972 Approved
0.6358 Remote Similarity NPD1608 Approved
0.6354 Remote Similarity NPD8455 Phase 2
0.6353 Remote Similarity NPD7097 Phase 1
0.635 Remote Similarity NPD4580 Approved
0.6347 Remote Similarity NPD6798 Discontinued
0.6337 Remote Similarity NPD7497 Discontinued
0.6337 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6004 Phase 3
0.6337 Remote Similarity NPD6002 Phase 3
0.6337 Remote Similarity NPD6005 Phase 3
0.6331 Remote Similarity NPD447 Suspended
0.633 Remote Similarity NPD2163 Approved
0.6328 Remote Similarity NPD1512 Approved
0.6322 Remote Similarity NPD7003 Approved
0.6316 Remote Similarity NPD4308 Phase 3
0.6316 Remote Similarity NPD1510 Phase 2
0.6312 Remote Similarity NPD5585 Approved
0.631 Remote Similarity NPD6233 Phase 2
0.6308 Remote Similarity NPD8435 Approved
0.6307 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6303 Remote Similarity NPD2798 Approved
0.6303 Remote Similarity NPD1019 Discontinued
0.6302 Remote Similarity NPD2968 Approved
0.6302 Remote Similarity NPD2971 Approved
0.629 Remote Similarity NPD5710 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data