Structure

Physi-Chem Properties

Molecular Weight:  344.09
Volume:  334.655
LogP:  3.099
LogD:  2.584
LogS:  -3.855
# Rotatable Bonds:  4
TPSA:  98.36
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.751
Synthetic Accessibility Score:  2.356
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.829
MDCK Permeability:  1.804340718081221e-05
Pgp-inhibitor:  0.954
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.024
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  87.92850494384766%
Volume Distribution (VD):  0.73
Pgp-substrate:  15.997026443481445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.813
CYP1A2-substrate:  0.973
CYP2C19-inhibitor:  0.393
CYP2C19-substrate:  0.18
CYP2C9-inhibitor:  0.734
CYP2C9-substrate:  0.83
CYP2D6-inhibitor:  0.195
CYP2D6-substrate:  0.891
CYP3A4-inhibitor:  0.474
CYP3A4-substrate:  0.324

ADMET: Excretion

Clearance (CL):  4.558
Half-life (T1/2):  0.755

ADMET: Toxicity

hERG Blockers:  0.133
Human Hepatotoxicity (H-HT):  0.092
Drug-inuced Liver Injury (DILI):  0.821
AMES Toxicity:  0.413
Rat Oral Acute Toxicity:  0.073
Maximum Recommended Daily Dose:  0.178
Skin Sensitization:  0.691
Carcinogencity:  0.058
Eye Corrosion:  0.003
Eye Irritation:  0.717
Respiratory Toxicity:  0.385

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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC47781

Natural Product ID:  NPC47781
Common Name*:   Cirsileneol
IUPAC Name:   5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:   Cirsileneol
Standard InCHIKey:  VKOSQMWSWLZQPA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
SMILES:  COc1cc(ccc1O)c1cc(=O)c2c(cc(c(c2O)OC)OC)o1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487213
PubChem CID:   162464
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88710-5]
NPO9625 Salvia tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50003a002]
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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO8374 Allium siculum Species Amaryllidaceae Eukaryota bulb n.a. n.a. PMID[12141853]
NPO2717 Vatica cinerea Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. PMID[12608862]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[15128261]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota Whole plant Songyang County, Zhejiang Province, China n.a. PMID[15387644]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. Oakham, MA, US n.a. PMID[16562853]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[17250743]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota leaves n.a. n.a. PMID[18357995]
NPO24475 Aceriphyllum rossii n.a. n.a. n.a. n.a. n.a. n.a. PMID[19618898]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO6706 Arthrobotrys oligospora Species Orbiliaceae Eukaryota n.a. n.a. n.a. PMID[21568306]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23186307]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
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]
NPO4347 Artemisia chinensis Species Asteraceae Eukaryota n.a. leaf n.a. PMID[24689280]
NPO4347 Artemisia chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24689280]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25919052]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31836445]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO1425 Salvia palaestina Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[6677714]
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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20640 Aloysia triphylla Species Verbenaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae 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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil 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]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris 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]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9625 Salvia tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata 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]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
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]
NPO25443 Citrus reticulata 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]
NPO4347 Artemisia chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9258 Plantago cornuti Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9625 Salvia tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4711 Goniothalamus thwaitesii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9625 Salvia tomentosa Species Lamiaceae 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]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31579 Artemisia capillaries Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO851 Eupatorium lindleyanum Species Asteraceae 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]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4487 Fritillaria thunbergii Species Liliaceae 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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17388 Schefferomitra subaequalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9258 Plantago cornuti Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26042 Agnorhiza bolanderi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO51 Petalonia fascia Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25291 Lactarius scrobiculatus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO979 Salvinia imbricata Species Salviniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23805 Arnica nevadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5442 Bryum weigelii Species Bryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25623 Taxodium mucronatum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24744 Chloranthus tianmushanensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6388 Mulguraea tridens Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14027 Dacryodes normandii Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23453 Pheidole pallidula Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5784 Walsura chrysogyne Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26128 Clonostachys rosea Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25326 Dendrosenecio kilimanjari Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11112 Inulanthera nuda Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22736 Drosera peltata Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4319 Rubia lanceolata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25144 Artemisia monogyna Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25390 Pterocarpus grandiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20823 Stenostomum lucidum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5646 Phoma violacea Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25045 Senecio squalidus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25187 Cladonia evansii Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7295 Arabis hirsuta Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24556 Bassia butyracea Species Abylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25090 Araujia sericifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24383 Ficus formosana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25234 Epaltes gariepina Species Asteraceae 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]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9625 Salvia tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23567 Coccus fagi Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18352 Anaxagorea clavata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6706 Arthrobotrys oligospora Species Orbiliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14201 Riccia fluitans Species Ricciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7552 Alligator mississippiensis Species Alligatoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24068 Prunus laurocerasus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25671 Gardenia fosbergii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6605 Neodiprion sertifer Species Diprionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24987 Simira eliezeriana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24640 Echinops amplexicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22194 Kaempferia pulchra Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25471 Chromolaena pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20640 Aloysia triphylla Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8374 Allium siculum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20833 Beyeria brevifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23691 Pyrosoma giganteum Species Pyrosomatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1794 Ilex affinis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25699 Vitex madiensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24675 Quercus aegilops Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24830 Prosopis glandulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7445 Pteris prolifera Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25258 Seriphidium cinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4873 Plectranthus sylvestris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2717 Vatica cinerea Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24929 Aria pallescens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24599 Streptomyces althioticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11435 Tulipa sylvestris Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9079 Tephrosia egregia Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24511 Dipterocarpus alatus Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25359 Isodon kameba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24291 Rhizobium phaseoli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4986 Eschscholzia californica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4347 Artemisia chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4711 Goniothalamus thwaitesii Species Annonaceae 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]
NPO4487 Fritillaria thunbergii Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23963 Odixia angusta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1425 Salvia palaestina Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10412 Aglaia erythrosperma Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25529 Bursaria spinosa Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25415 Pseudopterogorgia kallos Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24439 Tristagma uniflorum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6977 Triopha carpenteri Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6714 Securidaca inappendiculata Species Polygalaceae 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
NPO20640 NPC47781 Dried Or Powder n.a. 19.10071422 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO42032 NPC47781 n.a. n.a. 19.10071 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]

☑ 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
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 1.0 % PMID[528246]
NPT179 Cell Line A2780 Homo sapiens IC50 = 33.0 ug.mL-1 PMID[528248]
NPT762 Cell Line A-431 Homo sapiens IC50 = 33.0 ug.mL-1 PMID[528248]
NPT165 Cell Line HeLa Homo sapiens IC50 = 33.0 ug.mL-1 PMID[528248]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 33.0 ug.mL-1 PMID[528248]
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 6760.83 nM PMID[528247]

☑ 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 NPC47781 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
1.0 High Similarity NPC274327
1.0 High Similarity NPC22519
1.0 High Similarity NPC69394
1.0 High Similarity NPC231018
1.0 High Similarity NPC255350
1.0 High Similarity NPC176775
1.0 High Similarity NPC145379
1.0 High Similarity NPC160951
1.0 High Similarity NPC183878
0.9932 High Similarity NPC198826
0.9932 High Similarity NPC162313
0.9932 High Similarity NPC131624
0.9932 High Similarity NPC71334
0.9932 High Similarity NPC239128
0.9932 High Similarity NPC213622
0.9932 High Similarity NPC156222
0.9932 High Similarity NPC138360
0.9932 High Similarity NPC187498
0.9932 High Similarity NPC20830
0.9932 High Similarity NPC275722
0.9932 High Similarity NPC4455
0.9932 High Similarity NPC120163
0.9932 High Similarity NPC92659
0.9932 High Similarity NPC83508
0.9932 High Similarity NPC100887
0.9932 High Similarity NPC163780
0.9932 High Similarity NPC183597
0.9932 High Similarity NPC301323
0.9932 High Similarity NPC256612
0.9932 High Similarity NPC188203
0.9932 High Similarity NPC201136
0.9932 High Similarity NPC212678
0.9932 High Similarity NPC275836
0.9932 High Similarity NPC128863
0.9932 High Similarity NPC293183
0.9932 High Similarity NPC50715
0.9932 High Similarity NPC227325
0.9932 High Similarity NPC57030
0.9932 High Similarity NPC222830
0.9932 High Similarity NPC256283
0.9932 High Similarity NPC25270
0.9932 High Similarity NPC2476
0.9932 High Similarity NPC196439
0.9932 High Similarity NPC167815
0.9932 High Similarity NPC280339
0.9932 High Similarity NPC146165
0.9932 High Similarity NPC241498
0.9865 High Similarity NPC49824
0.9864 High Similarity NPC250822
0.9864 High Similarity NPC276409
0.9864 High Similarity NPC75279
0.9863 High Similarity NPC208043
0.9863 High Similarity NPC226973
0.9799 High Similarity NPC75215
0.9799 High Similarity NPC93376
0.9799 High Similarity NPC110070
0.9799 High Similarity NPC227192
0.9799 High Similarity NPC189179
0.9799 High Similarity NPC470402
0.9799 High Similarity NPC203891
0.9799 High Similarity NPC224137
0.9799 High Similarity NPC101830
0.9797 High Similarity NPC44079
0.9797 High Similarity NPC208197
0.9797 High Similarity NPC201451
0.9797 High Similarity NPC26227
0.9796 High Similarity NPC60972
0.9796 High Similarity NPC142540
0.9796 High Similarity NPC39732
0.9795 High Similarity NPC306821
0.9795 High Similarity NPC184136
0.9733 High Similarity NPC19687
0.9733 High Similarity NPC25495
0.9733 High Similarity NPC176300
0.9733 High Similarity NPC261004
0.9733 High Similarity NPC18772
0.9733 High Similarity NPC105242
0.9733 High Similarity NPC130894
0.9733 High Similarity NPC204854
0.9733 High Similarity NPC152166
0.9733 High Similarity NPC115798
0.9733 High Similarity NPC143828
0.9733 High Similarity NPC300943
0.9733 High Similarity NPC9609
0.9733 High Similarity NPC191459
0.9733 High Similarity NPC22472
0.9733 High Similarity NPC18607
0.9733 High Similarity NPC7846
0.9733 High Similarity NPC4481
0.9733 High Similarity NPC253634
0.9733 High Similarity NPC288669
0.9732 High Similarity NPC266960
0.9732 High Similarity NPC98661
0.9732 High Similarity NPC43243
0.9732 High Similarity NPC247017
0.9732 High Similarity NPC472916
0.9732 High Similarity NPC292107
0.9732 High Similarity NPC474520
0.9732 High Similarity NPC245546
0.973 High Similarity NPC86485
0.9728 High Similarity NPC308451
0.9726 High Similarity NPC223579
0.9726 High Similarity NPC177298
0.9726 High Similarity NPC328119
0.9726 High Similarity NPC183950
0.9726 High Similarity NPC48479
0.9726 High Similarity NPC296197
0.9726 High Similarity NPC216318
0.9726 High Similarity NPC17286
0.9726 High Similarity NPC259713
0.9726 High Similarity NPC287101
0.9726 High Similarity NPC52005
0.9726 High Similarity NPC137062
0.9669 High Similarity NPC476980
0.9667 High Similarity NPC472914
0.9667 High Similarity NPC176665
0.9667 High Similarity NPC29841
0.9667 High Similarity NPC472438
0.9667 High Similarity NPC48208
0.9667 High Similarity NPC96167
0.9667 High Similarity NPC472913
0.9667 High Similarity NPC475267
0.9667 High Similarity NPC163524
0.9667 High Similarity NPC474836
0.9667 High Similarity NPC472911
0.9667 High Similarity NPC472910
0.9667 High Similarity NPC78302
0.9667 High Similarity NPC235215
0.9667 High Similarity NPC245758
0.9667 High Similarity NPC287979
0.9667 High Similarity NPC474208
0.9667 High Similarity NPC222814
0.9667 High Similarity NPC162869
0.9667 High Similarity NPC78225
0.9667 High Similarity NPC7973
0.9667 High Similarity NPC156057
0.9667 High Similarity NPC305663
0.9664 High Similarity NPC2928
0.9664 High Similarity NPC32557
0.9664 High Similarity NPC189960
0.9662 High Similarity NPC301123
0.9662 High Similarity NPC120537
0.9662 High Similarity NPC180234
0.9662 High Similarity NPC199100
0.966 High Similarity NPC45873
0.9658 High Similarity NPC120464
0.9658 High Similarity NPC195202
0.9605 High Similarity NPC258331
0.9603 High Similarity NPC193842
0.96 High Similarity NPC200388
0.96 High Similarity NPC68093
0.96 High Similarity NPC178854
0.96 High Similarity NPC191146
0.96 High Similarity NPC55619
0.96 High Similarity NPC268161
0.96 High Similarity NPC100916
0.96 High Similarity NPC235165
0.96 High Similarity NPC265511
0.96 High Similarity NPC255106
0.9597 High Similarity NPC167091
0.9597 High Similarity NPC124714
0.9597 High Similarity NPC271779
0.9597 High Similarity NPC292214
0.9597 High Similarity NPC78326
0.9597 High Similarity NPC270620
0.9597 High Similarity NPC280937
0.9597 High Similarity NPC206238
0.9597 High Similarity NPC472915
0.9597 High Similarity NPC88645
0.9597 High Similarity NPC179126
0.9597 High Similarity NPC236223
0.9595 High Similarity NPC117579
0.9595 High Similarity NPC225731
0.9595 High Similarity NPC200740
0.9595 High Similarity NPC125062
0.9595 High Similarity NPC252933
0.9595 High Similarity NPC54394
0.9592 High Similarity NPC92722
0.9592 High Similarity NPC102003
0.9589 High Similarity NPC33265
0.9589 High Similarity NPC130230
0.9589 High Similarity NPC30647
0.9589 High Similarity NPC61871
0.9589 High Similarity NPC62536
0.9589 High Similarity NPC55557
0.9589 High Similarity NPC275772
0.9589 High Similarity NPC108406
0.9589 High Similarity NPC12200
0.9589 High Similarity NPC239312
0.9542 High Similarity NPC472448
0.9542 High Similarity NPC83922
0.9539 High Similarity NPC246478
0.9539 High Similarity NPC204290
0.9536 High Similarity NPC241904
0.9536 High Similarity NPC476981
0.9536 High Similarity NPC469584
0.9536 High Similarity NPC262286
0.9536 High Similarity NPC36852
0.9536 High Similarity NPC210084
0.9536 High Similarity NPC300727

  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 NPC47781 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
1.0 High Similarity NPD2801 Approved
0.94 High Similarity NPD1934 Approved
0.9384 High Similarity NPD1511 Approved
0.9257 High Similarity NPD1512 Approved
0.9216 High Similarity NPD3882 Suspended
0.9211 High Similarity NPD2393 Clinical (unspecified phase)
0.9026 High Similarity NPD3817 Phase 2
0.8938 High Similarity NPD3818 Discontinued
0.8931 High Similarity NPD6166 Phase 2
0.8931 High Similarity NPD6167 Clinical (unspecified phase)
0.8931 High Similarity NPD6168 Clinical (unspecified phase)
0.8896 High Similarity NPD4338 Clinical (unspecified phase)
0.8882 High Similarity NPD7054 Approved
0.8827 High Similarity NPD7472 Approved
0.8808 High Similarity NPD4378 Clinical (unspecified phase)
0.8712 High Similarity NPD7074 Phase 3
0.8679 High Similarity NPD5494 Approved
0.8659 High Similarity NPD6797 Phase 2
0.8608 High Similarity NPD4868 Clinical (unspecified phase)
0.8606 High Similarity NPD7251 Discontinued
0.8554 High Similarity NPD7808 Phase 3
0.8526 High Similarity NPD4380 Phase 2
0.8467 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD6232 Discontinued
0.8456 Intermediate Similarity NPD1510 Phase 2
0.8438 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8428 Intermediate Similarity NPD5402 Approved
0.8415 Intermediate Similarity NPD7473 Discontinued
0.8411 Intermediate Similarity NPD1549 Phase 2
0.84 Intermediate Similarity NPD2796 Approved
0.8377 Intermediate Similarity NPD6799 Approved
0.8323 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7075 Discontinued
0.8311 Intermediate Similarity NPD1240 Approved
0.8311 Intermediate Similarity NPD943 Approved
0.8282 Intermediate Similarity NPD1247 Approved
0.825 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD1465 Phase 2
0.8204 Intermediate Similarity NPD5844 Phase 1
0.82 Intermediate Similarity NPD1607 Approved
0.8187 Intermediate Similarity NPD6801 Discontinued
0.817 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD7819 Suspended
0.8107 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD3926 Phase 2
0.8063 Intermediate Similarity NPD6599 Discontinued
0.8041 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD2935 Discontinued
0.8013 Intermediate Similarity NPD447 Suspended
0.8013 Intermediate Similarity NPD230 Phase 1
0.8012 Intermediate Similarity NPD7411 Suspended
0.7987 Intermediate Similarity NPD5403 Approved
0.7973 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD6959 Discontinued
0.7949 Intermediate Similarity NPD3750 Approved
0.7947 Intermediate Similarity NPD1613 Approved
0.7947 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD919 Approved
0.7885 Intermediate Similarity NPD2800 Approved
0.7875 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD3027 Phase 3
0.7862 Intermediate Similarity NPD5401 Approved
0.7857 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD6559 Discontinued
0.7826 Intermediate Similarity NPD1653 Approved
0.7815 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD1551 Phase 2
0.7771 Intermediate Similarity NPD3749 Approved
0.775 Intermediate Similarity NPD2534 Approved
0.775 Intermediate Similarity NPD2532 Approved
0.775 Intermediate Similarity NPD2533 Approved
0.774 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD9494 Approved
0.7722 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD7768 Phase 2
0.7706 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD6190 Approved
0.7662 Intermediate Similarity NPD1933 Approved
0.7658 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD920 Approved
0.7643 Intermediate Similarity NPD2344 Approved
0.7633 Intermediate Similarity NPD7199 Phase 2
0.7628 Intermediate Similarity NPD3748 Approved
0.7619 Intermediate Similarity NPD6234 Discontinued
0.7616 Intermediate Similarity NPD3751 Discontinued
0.761 Intermediate Similarity NPD4628 Phase 3
0.7588 Intermediate Similarity NPD3787 Discontinued
0.7582 Intermediate Similarity NPD2313 Discontinued
0.758 Intermediate Similarity NPD6100 Approved
0.758 Intermediate Similarity NPD6099 Approved
0.7561 Intermediate Similarity NPD3226 Approved
0.7554 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD1243 Approved
0.7544 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2799 Discontinued
0.75 Intermediate Similarity NPD6651 Approved
0.75 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD5953 Discontinued
0.7483 Intermediate Similarity NPD1203 Approved
0.7472 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7286 Phase 2
0.7459 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD2309 Approved
0.7443 Intermediate Similarity NPD7685 Pre-registration
0.7425 Intermediate Similarity NPD37 Approved
0.7425 Intermediate Similarity NPD6844 Discontinued
0.7421 Intermediate Similarity NPD2346 Discontinued
0.7415 Intermediate Similarity NPD1548 Phase 1
0.7407 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD9269 Phase 2
0.7396 Intermediate Similarity NPD4966 Approved
0.7396 Intermediate Similarity NPD4965 Approved
0.7396 Intermediate Similarity NPD4967 Phase 2
0.7362 Intermediate Similarity NPD7390 Discontinued
0.7355 Intermediate Similarity NPD3268 Approved
0.7341 Intermediate Similarity NPD5242 Approved
0.7338 Intermediate Similarity NPD6832 Phase 2
0.7338 Intermediate Similarity NPD4908 Phase 1
0.7333 Intermediate Similarity NPD422 Phase 1
0.7325 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD2798 Approved
0.7314 Intermediate Similarity NPD7228 Approved
0.7308 Intermediate Similarity NPD6233 Phase 2
0.7296 Intermediate Similarity NPD7033 Discontinued
0.7285 Intermediate Similarity NPD9717 Approved
0.7284 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3018 Phase 2
0.7262 Intermediate Similarity NPD6385 Approved
0.7262 Intermediate Similarity NPD6386 Approved
0.7256 Intermediate Similarity NPD4357 Discontinued
0.7255 Intermediate Similarity NPD2797 Approved
0.7244 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD8434 Phase 2
0.7235 Intermediate Similarity NPD5353 Approved
0.723 Intermediate Similarity NPD5536 Phase 2
0.7222 Intermediate Similarity NPD2654 Approved
0.7219 Intermediate Similarity NPD1610 Phase 2
0.7219 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD2403 Approved
0.719 Intermediate Similarity NPD3225 Approved
0.7189 Intermediate Similarity NPD4360 Phase 2
0.7189 Intermediate Similarity NPD4363 Phase 3
0.7188 Intermediate Similarity NPD4308 Phase 3
0.7184 Intermediate Similarity NPD5711 Approved
0.7184 Intermediate Similarity NPD5710 Approved
0.7181 Intermediate Similarity NPD6776 Approved
0.7181 Intermediate Similarity NPD6777 Approved
0.7181 Intermediate Similarity NPD6781 Approved
0.7181 Intermediate Similarity NPD6778 Approved
0.7181 Intermediate Similarity NPD6780 Approved
0.7181 Intermediate Similarity NPD6782 Approved
0.7181 Intermediate Similarity NPD6779 Approved
0.7171 Intermediate Similarity NPD1608 Approved
0.7167 Intermediate Similarity NPD8313 Approved
0.7167 Intermediate Similarity NPD8312 Approved
0.7161 Intermediate Similarity NPD2861 Phase 2
0.7134 Intermediate Similarity NPD6798 Discontinued
0.7134 Intermediate Similarity NPD411 Approved
0.7133 Intermediate Similarity NPD9268 Approved
0.7124 Intermediate Similarity NPD2982 Phase 2
0.7124 Intermediate Similarity NPD2983 Phase 2
0.7117 Intermediate Similarity NPD1652 Phase 2
0.7111 Intermediate Similarity NPD7549 Discontinued
0.7108 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7229 Phase 3
0.7085 Intermediate Similarity NPD2899 Discontinued
0.707 Intermediate Similarity NPD4625 Phase 3
0.7068 Intermediate Similarity NPD7435 Discontinued
0.7066 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1481 Phase 2
0.7059 Intermediate Similarity NPD2981 Phase 2
0.7059 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4361 Phase 2
0.7059 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD228 Approved
0.7049 Intermediate Similarity NPD8150 Discontinued
0.7047 Intermediate Similarity NPD7584 Approved
0.7035 Intermediate Similarity NPD4288 Approved
0.7032 Intermediate Similarity NPD1470 Approved
0.7032 Intermediate Similarity NPD3267 Approved
0.7032 Intermediate Similarity NPD3266 Approved
0.7013 Intermediate Similarity NPD4749 Approved
0.7006 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6355 Discontinued
0.6994 Remote Similarity NPD7266 Discontinued
0.6993 Remote Similarity NPD1535 Discovery
0.6993 Remote Similarity NPD1201 Approved
0.699 Remote Similarity NPD7783 Phase 2
0.699 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7697 Approved
0.6979 Remote Similarity NPD7696 Phase 3

  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