Structure

Physi-Chem Properties

Molecular Weight:  204.19
Volume:  251.53
LogP:  5.802
LogD:  4.815
LogS:  -5.162
# Rotatable Bonds:  4
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.572
Synthetic Accessibility Score:  3.917
Fsp3:  0.6
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:  -4.653
MDCK Permeability:  2.006165414059069e-05
Pgp-inhibitor:  0.802
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.959
30% Bioavailability (F30%):  0.695

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.179
Plasma Protein Binding (PPB):  96.81237030029297%
Volume Distribution (VD):  5.108
Pgp-substrate:  3.0851848125457764%

ADMET: Metabolism

CYP1A2-inhibitor:  0.795
CYP1A2-substrate:  0.679
CYP2C19-inhibitor:  0.555
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.436
CYP2C9-substrate:  0.702
CYP2D6-inhibitor:  0.404
CYP2D6-substrate:  0.77
CYP3A4-inhibitor:  0.729
CYP3A4-substrate:  0.465

ADMET: Excretion

Clearance (CL):  14.814
Half-life (T1/2):  0.306

ADMET: Toxicity

hERG Blockers:  0.08
Human Hepatotoxicity (H-HT):  0.929
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.603
Skin Sensitization:  0.976
Carcinogencity:  0.239
Eye Corrosion:  0.092
Eye Irritation:  0.91
Respiratory Toxicity:  0.721

Download Data

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

  Natural Product: NPC183670

Natural Product ID:  NPC183670
Common Name*:   Alpha-Zingiberene
IUPAC Name:   (5S)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
Synonyms:   Alpha-Zingiberene
Standard InCHIKey:  KKOXKGNSUHTUBV-CABCVRRESA-N
Standard InCHI:  InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m1/s1
SMILES:  CC(=CCC[C@H]([C@@H]1CC=C(C=C1)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479020
PubChem CID:   11127403
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
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]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
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]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17996677]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota leaves and stems n.a. n.a. PMID[25442304]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota Radix n.a. n.a. PMID[29236488]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota Plant 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 n.a. n.a. Database[FooDB]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23332.1 Dendrobium fimbriatum var. oculatum Varieties Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30019 Curcuma sp Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9369 Curcuma sp. Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23332.1 Dendrobium fimbriatum var. oculatum Varieties Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17274 Rhizoma zingiberis recens preparata n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19335 Rhizoma zingiberis praeparata n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae 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]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae 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]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25094 Artemisia princeps Species Asteraceae 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]
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18951 Ligusticum sinense Species Apiaceae 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]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10492 Artemisia montana 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]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2838 Verbena officinalis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae 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
NPT2517 Organism Human rhinovirus 1B Human rhinovirus 1B ED50 = 1.9 ug PMID[559293]

☑ 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 NPC183670 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
0.9737 High Similarity NPC144023
0.9487 High Similarity NPC177470
0.9459 High Similarity NPC45727
0.9459 High Similarity NPC48638
0.8947 High Similarity NPC239039
0.8919 High Similarity NPC282119
0.875 High Similarity NPC120926
0.875 High Similarity NPC218918
0.8684 High Similarity NPC34764
0.8684 High Similarity NPC190810
0.8684 High Similarity NPC76145
0.8462 Intermediate Similarity NPC139717
0.8462 Intermediate Similarity NPC229262
0.8462 Intermediate Similarity NPC297643
0.8108 Intermediate Similarity NPC213749
0.8 Intermediate Similarity NPC266298
0.7949 Intermediate Similarity NPC92224
0.7838 Intermediate Similarity NPC206088
0.7838 Intermediate Similarity NPC3649
0.7727 Intermediate Similarity NPC248411
0.7727 Intermediate Similarity NPC202189
0.7568 Intermediate Similarity NPC60288
0.7556 Intermediate Similarity NPC86683
0.7556 Intermediate Similarity NPC114239
0.7556 Intermediate Similarity NPC296337
0.7556 Intermediate Similarity NPC13991
0.7556 Intermediate Similarity NPC241784
0.7447 Intermediate Similarity NPC17810
0.7297 Intermediate Similarity NPC138113
0.7273 Intermediate Similarity NPC473912
0.7255 Intermediate Similarity NPC470893
0.7234 Intermediate Similarity NPC124851
0.7111 Intermediate Similarity NPC60556
0.7111 Intermediate Similarity NPC109813
0.7111 Intermediate Similarity NPC86538
0.7083 Intermediate Similarity NPC17518
0.7027 Intermediate Similarity NPC64176
0.7027 Intermediate Similarity NPC262789
0.7027 Intermediate Similarity NPC288991
0.7021 Intermediate Similarity NPC323445
0.7021 Intermediate Similarity NPC159420
0.7 Intermediate Similarity NPC173592
0.7 Intermediate Similarity NPC99088
0.7 Intermediate Similarity NPC305759
0.6923 Remote Similarity NPC66577
0.6923 Remote Similarity NPC100879
0.6923 Remote Similarity NPC471327
0.6889 Remote Similarity NPC190232
0.6889 Remote Similarity NPC105246
0.6863 Remote Similarity NPC476679
0.6863 Remote Similarity NPC14002
0.6852 Remote Similarity NPC469769
0.6809 Remote Similarity NPC49088
0.68 Remote Similarity NPC26906
0.68 Remote Similarity NPC214584
0.6739 Remote Similarity NPC192529
0.6735 Remote Similarity NPC22765
0.6731 Remote Similarity NPC5626
0.6667 Remote Similarity NPC473728
0.6667 Remote Similarity NPC294358
0.6667 Remote Similarity NPC177112
0.6667 Remote Similarity NPC40417
0.6667 Remote Similarity NPC35519
0.6667 Remote Similarity NPC179169
0.6667 Remote Similarity NPC71506
0.6667 Remote Similarity NPC306195
0.6667 Remote Similarity NPC208638
0.6667 Remote Similarity NPC157781
0.6667 Remote Similarity NPC181255
0.66 Remote Similarity NPC32351
0.66 Remote Similarity NPC200129
0.6538 Remote Similarity NPC268564
0.6538 Remote Similarity NPC23117
0.6538 Remote Similarity NPC295777
0.6538 Remote Similarity NPC37644
0.6538 Remote Similarity NPC69898
0.6531 Remote Similarity NPC91962
0.6531 Remote Similarity NPC178644
0.65 Remote Similarity NPC151719
0.6491 Remote Similarity NPC469728
0.6481 Remote Similarity NPC55412
0.6481 Remote Similarity NPC249645
0.6471 Remote Similarity NPC244038
0.6444 Remote Similarity NPC227632
0.6444 Remote Similarity NPC62086
0.6444 Remote Similarity NPC78551
0.6429 Remote Similarity NPC475716
0.641 Remote Similarity NPC34671
0.641 Remote Similarity NPC115959
0.641 Remote Similarity NPC123965
0.64 Remote Similarity NPC106990
0.6364 Remote Similarity NPC208749
0.6364 Remote Similarity NPC321568
0.6364 Remote Similarity NPC281986
0.6364 Remote Similarity NPC22019
0.6346 Remote Similarity NPC68014
0.6316 Remote Similarity NPC176621
0.6304 Remote Similarity NPC188596
0.6304 Remote Similarity NPC103290
0.6296 Remote Similarity NPC469770
0.6275 Remote Similarity NPC329773
0.6275 Remote Similarity NPC176819
0.6275 Remote Similarity NPC163984
0.6275 Remote Similarity NPC58970
0.625 Remote Similarity NPC311852
0.6216 Remote Similarity NPC88325
0.6182 Remote Similarity NPC141699
0.6182 Remote Similarity NPC469967
0.617 Remote Similarity NPC193180
0.6154 Remote Similarity NPC138325
0.6154 Remote Similarity NPC27438
0.6122 Remote Similarity NPC210560
0.6122 Remote Similarity NPC165651
0.6122 Remote Similarity NPC24824
0.6102 Remote Similarity NPC474086
0.6087 Remote Similarity NPC246165
0.6071 Remote Similarity NPC475696
0.6071 Remote Similarity NPC165808
0.6071 Remote Similarity NPC474415
0.6071 Remote Similarity NPC470369
0.6071 Remote Similarity NPC474528
0.6071 Remote Similarity NPC470370
0.6053 Remote Similarity NPC266144
0.6053 Remote Similarity NPC266539
0.6053 Remote Similarity NPC31891
0.6053 Remote Similarity NPC287191
0.6047 Remote Similarity NPC182392
0.6042 Remote Similarity NPC269862
0.6 Remote Similarity NPC130209
0.6 Remote Similarity NPC195246
0.6 Remote Similarity NPC148216
0.6 Remote Similarity NPC123194
0.6 Remote Similarity NPC262558
0.6 Remote Similarity NPC8610
0.6 Remote Similarity NPC148163
0.6 Remote Similarity NPC232247
0.6 Remote Similarity NPC251666
0.6 Remote Similarity NPC276009
0.6 Remote Similarity NPC22098
0.5965 Remote Similarity NPC60772
0.5962 Remote Similarity NPC182102
0.5962 Remote Similarity NPC26960
0.5957 Remote Similarity NPC469969
0.5957 Remote Similarity NPC473614
0.5932 Remote Similarity NPC326645
0.5932 Remote Similarity NPC329416
0.5932 Remote Similarity NPC225342
0.5932 Remote Similarity NPC317177
0.5932 Remote Similarity NPC135924
0.5932 Remote Similarity NPC317025
0.5926 Remote Similarity NPC45283
0.5918 Remote Similarity NPC114841
0.5902 Remote Similarity NPC198023
0.5902 Remote Similarity NPC155172
0.5902 Remote Similarity NPC268039
0.5902 Remote Similarity NPC32312
0.5897 Remote Similarity NPC10183
0.5893 Remote Similarity NPC4881
0.5893 Remote Similarity NPC473733
0.5862 Remote Similarity NPC474420
0.5862 Remote Similarity NPC472304
0.5862 Remote Similarity NPC474455
0.5862 Remote Similarity NPC276764
0.5862 Remote Similarity NPC143834
0.5862 Remote Similarity NPC474454
0.5849 Remote Similarity NPC64866
0.5849 Remote Similarity NPC30433
0.5833 Remote Similarity NPC67761
0.5833 Remote Similarity NPC174956
0.5833 Remote Similarity NPC209279
0.5833 Remote Similarity NPC108494
0.5833 Remote Similarity NPC88079
0.5833 Remote Similarity NPC68889
0.5833 Remote Similarity NPC194586
0.5833 Remote Similarity NPC180871
0.5833 Remote Similarity NPC197238
0.5833 Remote Similarity NPC202118
0.5833 Remote Similarity NPC51758
0.5818 Remote Similarity NPC202850
0.5818 Remote Similarity NPC105780
0.5818 Remote Similarity NPC209431
0.5818 Remote Similarity NPC100809
0.5818 Remote Similarity NPC63396
0.5818 Remote Similarity NPC168518
0.5814 Remote Similarity NPC62779
0.5806 Remote Similarity NPC255781
0.5806 Remote Similarity NPC149680
0.58 Remote Similarity NPC166788
0.5789 Remote Similarity NPC11130
0.5789 Remote Similarity NPC269586
0.5789 Remote Similarity NPC38513
0.5789 Remote Similarity NPC474457
0.5789 Remote Similarity NPC115385
0.5769 Remote Similarity NPC62755
0.5769 Remote Similarity NPC234597
0.5763 Remote Similarity NPC135648
0.5763 Remote Similarity NPC127582
0.5763 Remote Similarity NPC311809
0.5763 Remote Similarity NPC66020
0.575 Remote Similarity NPC179103

  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 NPC183670 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
0.8684 High Similarity NPD319 Phase 1
0.7447 Intermediate Similarity NPD8262 Approved
0.6889 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6481 Remote Similarity NPD4219 Approved
0.6 Remote Similarity NPD342 Phase 1
0.5932 Remote Similarity NPD4194 Approved
0.5932 Remote Similarity NPD4191 Approved
0.5932 Remote Similarity NPD4193 Approved
0.5932 Remote Similarity NPD4192 Approved
0.5738 Remote Similarity NPD5325 Clinical (unspecified phase)
0.569 Remote Similarity NPD287 Approved
0.5667 Remote Similarity NPD368 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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