Structure

Physi-Chem Properties

Molecular Weight:  314.17
Volume:  315.648
LogP:  1.055
LogD:  1.169
LogS:  -1.369
# Rotatable Bonds:  5
TPSA:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.537
Synthetic Accessibility Score:  4.243
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.094
MDCK Permeability:  7.047721010167152e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.059
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.176
Plasma Protein Binding (PPB):  48.36770248413086%
Volume Distribution (VD):  0.833
Pgp-substrate:  49.150508880615234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.074
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.131
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.069
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.192
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.093

ADMET: Excretion

Clearance (CL):  2.376
Half-life (T1/2):  0.865

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.14
Drug-inuced Liver Injury (DILI):  0.082
AMES Toxicity:  0.592
Rat Oral Acute Toxicity:  0.082
Maximum Recommended Daily Dose:  0.573
Skin Sensitization:  0.179
Carcinogencity:  0.94
Eye Corrosion:  0.004
Eye Irritation:  0.182
Respiratory Toxicity:  0.73

Download Data

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

  Natural Product: NPC176025

Natural Product ID:  NPC176025
Common Name*:   MDCGEAGEQVMWPE-PLWSPRCSSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MDCGEAGEQVMWPE-PLWSPRCSSA-N
Standard InCHI:  InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,10,12,14H,8H2,1-4H3/b6-5+/t10-,12-/m1/s1
SMILES:  CC1=CC(=O)CC(C)(C)[C@@H]1/C=C/[C@@H](C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   124355562
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.bse.2004.02.008]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/01496395.2011.635623]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. seed n.a. PMID[10661881]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO15659 Zanthoxylum tetraspermum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11324918]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. PMID[11430011]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO12848 Carpinus cordata Species Betulaceae Eukaryota stems n.a. n.a. PMID[12350169]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[14600382]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[15387673]
NPO15063 Leathesia nana Species Chordariaceae Eukaryota n.a. n.a. n.a. PMID[15497936]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota stem bark Veikabu bridge along the Hiritano highway 40 km from Port Moresby, Papua New Guinea 1998-FEB PMID[16038553]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO11917 Asterospicularia laurae Species Xeniidae Eukaryota n.a. n.a. n.a. PMID[19863101]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[20121250]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO4181 Pseudoalteromonas luteoviolacea Species Pseudoalteromonadaceae Bacteria n.a. n.a. n.a. PMID[20973551]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. Hainan soft coral n.a. PMID[23357636]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25611131]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[25894905]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. whole plant n.a. PMID[28294414]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[28358502]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[464561]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7513747]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7561895]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root Essent. Oil n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11641 Solanum laxum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15697 Camellia sasanqua Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14936 Agave shawii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5866 Bitis arietans Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4325 Blastochloris viridis Species Hyphomicrobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16089 Dumortiera hirsuta Species Dumortieraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11808 Ania latifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17702 Astragalus sempervirens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12490 Lecidea speirodes Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14395 Lysimachia mauritiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17865 Amathia pinnata Species Vesiculariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16493 Nasutitermes ephratae Species Termitoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12848 Carpinus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20219 Rhizobium etli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4589 Sarcotragus spinosulus Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15467 Hedysarum connatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15063 Leathesia nana Species Chordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8506 Cotyledon secunda Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17400 Peltostigma guatemalense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6881 Caragana aurantiaca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4181 Pseudoalteromonas luteoviolacea Species Pseudoalteromonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11436 Baeomyces roseus Species Baeomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO820 Grindelia perennis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2507 Rumex maritimus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27733 Rosa hybrid cultivar Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15697 Camellia sasanqua Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7562 Premna odorata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16557 Polygala ruwenzoriensis Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16125 Micromonas pusilla Species Mamiellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24409 Evasterias troschelii Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9479 Ambrosia grayi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10417 Ipomoea digitata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14313 Pachybasium candidum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5047 Evodiopanax innovans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15659 Zanthoxylum tetraspermum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10989 Annona cornifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17633 Viguiera incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2827 Plumeria alba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12703 Eucalyptus melliodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15349 Acacia sparsiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11917 Asterospicularia laurae Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16369 Lepisorus ussuriensis Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14807 Arenaria juncea Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15205 Alaria crispa Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12293 Euphorbia iberica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13407 Goniothalamus malayanus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16796 Rumex conglomeratus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17169 Adiantum lunulatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21724 Sabina sargentii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17472 Drechslera avenae Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13442 Eucalyptus regnans Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15588 Senecio desfontainei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8804 Raputia simulans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17544 Acacia adunca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18022 Naucleopsis ternstroemiiflora Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17942 Wikstroemia retusa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15797 Drypetes littoralis Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15552 Anacystis montana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11641 Solanum laxum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14859 Bishovia boliviensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17786 Marrubium anisodon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13139 Anatheca montagnei Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11002 Hopea jucunda Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11994 Thesium humile Species Thesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11987 Silene inflata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17242 Laurencia spectabilis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16025 Werneria decora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15227 Helipterum roseum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16718 Pinna nobilis Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3964 Calostephane divaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2038 Myrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16731 Phoebe pittieri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14463 Dirca occidentalis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16475 Plumbago pulchella Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15803 Artemisia assoana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11538 Salvia syriaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16611 Alstonia spathulata Species Apocynaceae 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

☑ 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 NPC176025 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

  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 NPC176025 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

  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