Structure

Physi-Chem Properties

Molecular Weight:  204.19
Volume:  245.61
LogP:  5.341
LogD:  4.242
LogS:  -5.23
# Rotatable Bonds:  1
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.542
Synthetic Accessibility Score:  4.011
Fsp3:  0.733
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.543
MDCK Permeability:  1.6756932382122613e-05
Pgp-inhibitor:  0.504
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.806
30% Bioavailability (F30%):  0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.099
Plasma Protein Binding (PPB):  94.58480072021484%
Volume Distribution (VD):  2.921
Pgp-substrate:  3.7737131118774414%

ADMET: Metabolism

CYP1A2-inhibitor:  0.637
CYP1A2-substrate:  0.746
CYP2C19-inhibitor:  0.375
CYP2C19-substrate:  0.935
CYP2C9-inhibitor:  0.284
CYP2C9-substrate:  0.701
CYP2D6-inhibitor:  0.197
CYP2D6-substrate:  0.855
CYP3A4-inhibitor:  0.738
CYP3A4-substrate:  0.309

ADMET: Excretion

Clearance (CL):  6.842
Half-life (T1/2):  0.141

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.198
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.919
Skin Sensitization:  0.548
Carcinogencity:  0.744
Eye Corrosion:  0.929
Eye Irritation:  0.98
Respiratory Toxicity:  0.656

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Similar NPs/Drugs  

  Natural Product: NPC86683

Natural Product ID:  NPC86683
Common Name*:   (3R,4As,5R)-4A,5-Dimethyl-3-Prop-1-En-2-Yl-2,3,4,5,6,7-Hexahydro-1H-Naphthalene
IUPAC Name:   (3R,4aS,5R)-4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
Synonyms:  
Standard InCHIKey:  QEBNYNLSCGVZOH-NFAWXSAZSA-N
Standard InCHI:  InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1
SMILES:  CC(=C)[C@@H]1CCC2=CCC[C@H]([C@@]2(C1)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3186909
PubChem CID:   9855795
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(81)85171-0]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1039/C8GC03728K]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[19245261]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20151678]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20853876]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[20929806]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21268200]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22544021]
NPO41690 Escherichia coli LAFCmlcPU [alsS, kivD, ilvC, ilvD, adhA ldhA adhE pflB pta-ackA mlc] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22561880]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22851214]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22909174]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23113661]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23727191]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23864262]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26062534]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26358188]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26488898]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26951651]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[27825357]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[29077207]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[29096626]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30061932]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30496827]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30684358]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[32830192]
NPO41714 Escherichia coli WΔ4IB4 [budB ilvCFBR ilvD kdcA adhAFBR ldhA adhE pta frdA] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[33068182]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[33195815]
NPO41850 A new engineered strain of Escherichia coli [n.a.] Strain Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[34824227]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
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]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae 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]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17295 Chrysanthemum zawadskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae 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]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae 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]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22715 Alpinia oxyphylla Species Zingiberaceae 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]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17295 Chrysanthemum zawadskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3987 Syzygium aromaticum Species Myrtaceae 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 30895.6 nM PubChem BioAssay data set
NPT472 Individual Protein Vanilloid receptor Homo sapiens Activity = 31.0 % PMID[452072]
NPT472 Individual Protein Vanilloid receptor Homo sapiens Inhibition = 69.0 % PMID[452072]
NPT169 Cell Line B16-F10 Mus musculus Activity = 94.82 % PMID[452072]
NPT169 Cell Line B16-F10 Mus musculus Activity = 82.66 % PMID[452072]
NPT169 Cell Line B16-F10 Mus musculus Activity = 41.58 % PMID[452072]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 9.9 % PMID[452072]
NPT2 Others Unspecified Potency n.a. 34665.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 218.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15355.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38895.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43641.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT22464 SINGLE PROTEIN Calcium release-activated calcium channel protein 1 Homo sapiens Activity = 5.0 % PMID[452072]
NPT22464 SINGLE PROTEIN Calcium release-activated calcium channel protein 1 Homo sapiens Inhibition = 94.0 % PMID[452072]
NPT22464 SINGLE PROTEIN Calcium release-activated calcium channel protein 1 Homo sapiens Inhibition = 13.0 % PMID[452072]
NPT22464 SINGLE PROTEIN Calcium release-activated calcium channel protein 1 Homo sapiens Inhibition = 45.0 % PMID[452072]
NPT2 Others Unspecified Activity = 53.0 % PMID[452072]
NPT2 Others Unspecified Activity = 75.0 % PMID[452072]
NPT2 Others Unspecified Activity = 85.0 % PMID[452072]

☑ 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 NPC86683 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
0.9333 High Similarity NPC17518
0.907 High Similarity NPC192529
0.8913 High Similarity NPC22765
0.8864 High Similarity NPC202189
0.8696 High Similarity NPC124851
0.8667 High Similarity NPC241784
0.8667 High Similarity NPC13991
0.8667 High Similarity NPC114239
0.8667 High Similarity NPC296337
0.8605 High Similarity NPC103290
0.8444 Intermediate Similarity NPC248411
0.8409 Intermediate Similarity NPC193180
0.8409 Intermediate Similarity NPC105246
0.8409 Intermediate Similarity NPC190232
0.8235 Intermediate Similarity NPC469770
0.8 Intermediate Similarity NPC473728
0.8 Intermediate Similarity NPC177470
0.7959 Intermediate Similarity NPC200129
0.7955 Intermediate Similarity NPC62086
0.7955 Intermediate Similarity NPC227632
0.7955 Intermediate Similarity NPC78551
0.7925 Intermediate Similarity NPC474415
0.7925 Intermediate Similarity NPC475696
0.7925 Intermediate Similarity NPC474528
0.7907 Intermediate Similarity NPC139717
0.7907 Intermediate Similarity NPC297643
0.7907 Intermediate Similarity NPC229262
0.7885 Intermediate Similarity NPC123194
0.7826 Intermediate Similarity NPC60556
0.7826 Intermediate Similarity NPC86538
0.7826 Intermediate Similarity NPC109813
0.7778 Intermediate Similarity NPC469769
0.7778 Intermediate Similarity NPC144023
0.7755 Intermediate Similarity NPC17810
0.7674 Intermediate Similarity NPC190810
0.7674 Intermediate Similarity NPC76145
0.7674 Intermediate Similarity NPC34764
0.7636 Intermediate Similarity NPC474454
0.7636 Intermediate Similarity NPC474455
0.7636 Intermediate Similarity NPC475716
0.7636 Intermediate Similarity NPC474420
0.7593 Intermediate Similarity NPC474457
0.7556 Intermediate Similarity NPC183670
0.7547 Intermediate Similarity NPC470893
0.75 Intermediate Similarity NPC311809
0.75 Intermediate Similarity NPC127582
0.75 Intermediate Similarity NPC49088
0.75 Intermediate Similarity NPC239039
0.7455 Intermediate Similarity NPC60772
0.7368 Intermediate Similarity NPC469728
0.7347 Intermediate Similarity NPC323445
0.7273 Intermediate Similarity NPC470369
0.7273 Intermediate Similarity NPC470370
0.7273 Intermediate Similarity NPC11130
0.7255 Intermediate Similarity NPC476681
0.7241 Intermediate Similarity NPC202118
0.7241 Intermediate Similarity NPC197238
0.7234 Intermediate Similarity NPC473912
0.717 Intermediate Similarity NPC14002
0.717 Intermediate Similarity NPC23117
0.7143 Intermediate Similarity NPC213749
0.7119 Intermediate Similarity NPC285371
0.7119 Intermediate Similarity NPC475124
0.7119 Intermediate Similarity NPC469662
0.7111 Intermediate Similarity NPC48638
0.7111 Intermediate Similarity NPC45727
0.7083 Intermediate Similarity NPC141777
0.7083 Intermediate Similarity NPC166362
0.7083 Intermediate Similarity NPC227670
0.7045 Intermediate Similarity NPC92224
0.7037 Intermediate Similarity NPC5626
0.7021 Intermediate Similarity NPC120926
0.7021 Intermediate Similarity NPC218918
0.7018 Intermediate Similarity NPC276764
0.7018 Intermediate Similarity NPC472304
0.7018 Intermediate Similarity NPC309825
0.6949 Remote Similarity NPC81615
0.6949 Remote Similarity NPC474086
0.6905 Remote Similarity NPC3649
0.6897 Remote Similarity NPC176621
0.6897 Remote Similarity NPC135648
0.6885 Remote Similarity NPC242945
0.6885 Remote Similarity NPC92327
0.6885 Remote Similarity NPC222366
0.6885 Remote Similarity NPC259156
0.6885 Remote Similarity NPC286669
0.6885 Remote Similarity NPC176171
0.6885 Remote Similarity NPC279434
0.6885 Remote Similarity NPC476039
0.6863 Remote Similarity NPC178644
0.6852 Remote Similarity NPC127944
0.6852 Remote Similarity NPC476679
0.6852 Remote Similarity NPC474416
0.6842 Remote Similarity NPC56905
0.6842 Remote Similarity NPC27610
0.6833 Remote Similarity NPC169275
0.6833 Remote Similarity NPC52449
0.6809 Remote Similarity NPC246165
0.68 Remote Similarity NPC229403
0.6786 Remote Similarity NPC179024
0.678 Remote Similarity NPC194208
0.678 Remote Similarity NPC282694
0.678 Remote Similarity NPC60565
0.678 Remote Similarity NPC79576
0.678 Remote Similarity NPC213152
0.678 Remote Similarity NPC219621
0.6774 Remote Similarity NPC4370
0.6774 Remote Similarity NPC193770
0.6774 Remote Similarity NPC197805
0.6774 Remote Similarity NPC176107
0.6774 Remote Similarity NPC171225
0.6774 Remote Similarity NPC290350
0.6739 Remote Similarity NPC266298
0.6727 Remote Similarity NPC476683
0.6724 Remote Similarity NPC472827
0.6721 Remote Similarity NPC268039
0.6721 Remote Similarity NPC107258
0.6721 Remote Similarity NPC163678
0.6667 Remote Similarity NPC20610
0.6667 Remote Similarity NPC208999
0.6667 Remote Similarity NPC155198
0.6667 Remote Similarity NPC288253
0.6667 Remote Similarity NPC181255
0.6667 Remote Similarity NPC157781
0.6667 Remote Similarity NPC35519
0.6667 Remote Similarity NPC188292
0.6667 Remote Similarity NPC174956
0.6667 Remote Similarity NPC39157
0.6667 Remote Similarity NPC306195
0.6667 Remote Similarity NPC260474
0.6667 Remote Similarity NPC296697
0.6667 Remote Similarity NPC476945
0.6667 Remote Similarity NPC142754
0.6667 Remote Similarity NPC145715
0.6667 Remote Similarity NPC179169
0.6667 Remote Similarity NPC283247
0.6667 Remote Similarity NPC82477
0.6667 Remote Similarity NPC310992
0.6667 Remote Similarity NPC216460
0.6667 Remote Similarity NPC282119
0.6613 Remote Similarity NPC323005
0.6613 Remote Similarity NPC149680
0.6613 Remote Similarity NPC185587
0.661 Remote Similarity NPC317778
0.6607 Remote Similarity NPC200258
0.6562 Remote Similarity NPC138409
0.6562 Remote Similarity NPC474248
0.6562 Remote Similarity NPC182815
0.6562 Remote Similarity NPC184919
0.6562 Remote Similarity NPC139397
0.6562 Remote Similarity NPC286814
0.6557 Remote Similarity NPC473959
0.6557 Remote Similarity NPC290367
0.6557 Remote Similarity NPC6697
0.6557 Remote Similarity NPC212210
0.6557 Remote Similarity NPC329698
0.6552 Remote Similarity NPC308108
0.6552 Remote Similarity NPC311852
0.6552 Remote Similarity NPC170799
0.6545 Remote Similarity NPC69898
0.6545 Remote Similarity NPC295777
0.6512 Remote Similarity NPC66577
0.6512 Remote Similarity NPC206088
0.6508 Remote Similarity NPC69649
0.6508 Remote Similarity NPC68703
0.6508 Remote Similarity NPC220210
0.6508 Remote Similarity NPC20181
0.6491 Remote Similarity NPC55412
0.6491 Remote Similarity NPC39068
0.6491 Remote Similarity NPC264779
0.6491 Remote Similarity NPC249645
0.6481 Remote Similarity NPC26906
0.6481 Remote Similarity NPC236623
0.6481 Remote Similarity NPC214584
0.6462 Remote Similarity NPC145498
0.6462 Remote Similarity NPC307176
0.6462 Remote Similarity NPC34834
0.6462 Remote Similarity NPC159577
0.6462 Remote Similarity NPC265782
0.6462 Remote Similarity NPC2634
0.6462 Remote Similarity NPC475728
0.6462 Remote Similarity NPC92801
0.6462 Remote Similarity NPC35734
0.6462 Remote Similarity NPC251929
0.6462 Remote Similarity NPC282593
0.6462 Remote Similarity NPC260040
0.6452 Remote Similarity NPC251118
0.6406 Remote Similarity NPC87141
0.6406 Remote Similarity NPC96484
0.6406 Remote Similarity NPC94192
0.6406 Remote Similarity NPC160209
0.6406 Remote Similarity NPC32055
0.64 Remote Similarity NPC51762
0.64 Remote Similarity NPC90506
0.64 Remote Similarity NPC90803
0.64 Remote Similarity NPC474118
0.64 Remote Similarity NPC23145
0.6379 Remote Similarity NPC208749
0.6379 Remote Similarity NPC321568
0.6379 Remote Similarity NPC22019

  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 NPC86683 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
0.8409 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD8262 Approved
0.7674 Intermediate Similarity NPD319 Phase 1
0.6667 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4137 Phase 3
0.6552 Remote Similarity NPD287 Approved
0.6491 Remote Similarity NPD4219 Approved
0.6462 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6462 Remote Similarity NPD6939 Phase 2
0.6462 Remote Similarity NPD4691 Approved
0.6462 Remote Similarity NPD4747 Approved
0.6364 Remote Similarity NPD5276 Approved
0.6364 Remote Similarity NPD4243 Approved
0.6176 Remote Similarity NPD4058 Approved
0.6176 Remote Similarity NPD4785 Approved
0.6176 Remote Similarity NPD4784 Approved
0.6176 Remote Similarity NPD4687 Approved
0.6176 Remote Similarity NPD5733 Approved
0.6087 Remote Similarity NPD5275 Approved
0.6087 Remote Similarity NPD6942 Approved
0.6087 Remote Similarity NPD7339 Approved
0.6087 Remote Similarity NPD4190 Phase 3
0.6061 Remote Similarity NPD6923 Approved
0.6061 Remote Similarity NPD6922 Approved
0.6 Remote Similarity NPD3701 Clinical (unspecified phase)
0.597 Remote Similarity NPD7144 Approved
0.597 Remote Similarity NPD7143 Approved
0.5968 Remote Similarity NPD4192 Approved
0.5968 Remote Similarity NPD4191 Approved
0.5968 Remote Similarity NPD4194 Approved
0.5968 Remote Similarity NPD4193 Approved
0.5882 Remote Similarity NPD7152 Approved
0.5882 Remote Similarity NPD7150 Approved
0.5882 Remote Similarity NPD7151 Approved
0.5857 Remote Similarity NPD8264 Approved
0.5781 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5753 Remote Similarity NPD7645 Phase 2
0.5753 Remote Similarity NPD4195 Approved
0.5714 Remote Similarity NPD6926 Approved
0.5714 Remote Similarity NPD6924 Approved
0.5676 Remote Similarity NPD4695 Discontinued

  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