Structure

Physi-Chem Properties

Molecular Weight:  204.19
Volume:  251.53
LogP:  6.296
LogD:  4.636
LogS:  -5.637
# 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:  0.563
Synthetic Accessibility Score:  3.431
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:  -4.56
MDCK Permeability:  1.4533802641381044e-05
Pgp-inhibitor:  0.967
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.956
30% Bioavailability (F30%):  0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.27
Plasma Protein Binding (PPB):  97.953857421875%
Volume Distribution (VD):  4.429
Pgp-substrate:  3.5442068576812744%

ADMET: Metabolism

CYP1A2-inhibitor:  0.888
CYP1A2-substrate:  0.272
CYP2C19-inhibitor:  0.448
CYP2C19-substrate:  0.5
CYP2C9-inhibitor:  0.318
CYP2C9-substrate:  0.852
CYP2D6-inhibitor:  0.072
CYP2D6-substrate:  0.545
CYP3A4-inhibitor:  0.251
CYP3A4-substrate:  0.203

ADMET: Excretion

Clearance (CL):  11.552
Half-life (T1/2):  0.128

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.863
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.007
Maximum Recommended Daily Dose:  0.233
Skin Sensitization:  0.761
Carcinogencity:  0.487
Eye Corrosion:  0.313
Eye Irritation:  0.976
Respiratory Toxicity:  0.032

Download Data

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

  Natural Product: NPC139717

Natural Product ID:  NPC139717
Common Name*:   Beta-Bisabolene
IUPAC Name:   (4R)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohexene
Synonyms:   Beta-Bisabolene
Standard InCHIKey:  XZRVRYFILCSYSP-HNNXBMFYSA-N
Standard InCHI:  InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m0/s1
SMILES:  CC(=CCCC(=C)[C@H]1CC=C(C)CC1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444389
PubChem CID:   68128
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
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/S0031-9422(01)00459-9]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[11575963]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[12662092]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. stem n.a. PMID[12770595]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[1294697]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. whole plant n.a. PMID[15356999]
NPO1396 Cladogynos orientalis n.a. n.a. n.a. n.a. n.a. n.a. PMID[15679308]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. Caribbean n.a. PMID[1686898]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1800637]
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]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. stem n.a. PMID[21226514]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota roots n.a. n.a. PMID[24940955]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2607355]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[26281591]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2809609]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Seeds n.a. n.a. PMID[28134521]
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]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[3404159]
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]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8158155]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8277307]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota Pt 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]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8306 Berneuxia thibetica Species Diapensiaceae 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]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20553 Zingiber officinale Species Zingiberaceae 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]
NPO27681 Mikania grazielae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28061 Gyrothyra underwoodiana Species Gyrothyraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8132 Fritillaria meleagris Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19991 Mantella aurantiaca Species Mantellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27318 Sideritis lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27861 Laggera aurita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28049 Piper callosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28208 Salvia dichroa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28262 Marasmius graminum Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2323 Plantago lundborgii Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28174 Poterium sanguisorba Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2008 Streptomyces ehimensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28253 Ceratiomyxa fruticulosa Species Ceratiomyxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27480 Pinna muricata Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28191 Hardwickia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28139 Umbilicaria pustulata Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1706 Eragrostis curvula Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17152 Pittocaulon bombycophole Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28512 Astragalus glycyphyllos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28330 Colchicum arenarium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1396 Cladogynos orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23272 Cassinia subtropica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4836 Sideritis arborescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27532 Lamprolobium fruticosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28321 Cortinellus berkeleyanus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8950 Stilpnopappus pickelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4094 Aspergillus ruber Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28555 Adina trichotoma Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16983 Persea obovatifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28499 Aethalium septicum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16927 Erodendrum neriifolium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO643 Astragalus ernestii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4266 Botryotrichum murorum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5339 Isophysis tasmanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3445 Dumoria heckeli n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20121 Afraegle paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28568 Hippeastrum aulicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1203 Solanum pseudoquina Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27350 Scytalidium uredinicola Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28074 Dianella revoluta Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8433 Bongardia chrysogonum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28006 Pinus pumila Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17179 Elizabethkingia meningoseptica Species Flavobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27894 Rubus pungens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO117 Acacia armata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21493 Bunodosoma caissarum Species Actiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1541 Clusia ellipticifolia Species Clusiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28168 Armina maculata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27220 Centaurea cheiranthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15295 Polyachyrus sphaerocephalus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28305 Daphnandra johnsonii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27334 Siphula roccellaeformis Species Icmadophilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28345 Cladanthus arabicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1049 Tethya amamensis Species Tethyidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7793 Matricaria matricarioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13682 Lonchocarpus laxiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28534 Athrixia elata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9367 Jacobaea argunensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9138 Syzygium cumini 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
NPT2517 Organism Human rhinovirus 1B Human rhinovirus 1B ED50 = 14.3 ug PMID[575503]

☑ 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 NPC139717 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 NPC297643
1.0 High Similarity NPC229262
0.9714 High Similarity NPC190810
0.9714 High Similarity NPC34764
0.9714 High Similarity NPC76145
0.8571 High Similarity NPC213749
0.8537 High Similarity NPC202189
0.8537 High Similarity NPC248411
0.85 High Similarity NPC177470
0.8462 Intermediate Similarity NPC183670
0.8421 Intermediate Similarity NPC239039
0.8378 Intermediate Similarity NPC92224
0.8333 Intermediate Similarity NPC296337
0.8286 Intermediate Similarity NPC3649
0.825 Intermediate Similarity NPC144023
0.7949 Intermediate Similarity NPC45727
0.7949 Intermediate Similarity NPC48638
0.7907 Intermediate Similarity NPC241784
0.7907 Intermediate Similarity NPC13991
0.7907 Intermediate Similarity NPC114239
0.7907 Intermediate Similarity NPC86683
0.7895 Intermediate Similarity NPC282119
0.7778 Intermediate Similarity NPC206088
0.7778 Intermediate Similarity NPC17518
0.7619 Intermediate Similarity NPC473912
0.7556 Intermediate Similarity NPC124851
0.75 Intermediate Similarity NPC266298
0.7447 Intermediate Similarity NPC244038
0.7442 Intermediate Similarity NPC86538
0.7442 Intermediate Similarity NPC109813
0.7442 Intermediate Similarity NPC192529
0.7442 Intermediate Similarity NPC60556
0.7391 Intermediate Similarity NPC22765
0.7381 Intermediate Similarity NPC120926
0.7381 Intermediate Similarity NPC218918
0.7297 Intermediate Similarity NPC471327
0.7297 Intermediate Similarity NPC100879
0.7292 Intermediate Similarity NPC179169
0.7292 Intermediate Similarity NPC306195
0.7292 Intermediate Similarity NPC181255
0.7292 Intermediate Similarity NPC473728
0.7292 Intermediate Similarity NPC157781
0.7292 Intermediate Similarity NPC35519
0.7234 Intermediate Similarity NPC200129
0.7209 Intermediate Similarity NPC105246
0.7209 Intermediate Similarity NPC190232
0.7174 Intermediate Similarity NPC91962
0.7111 Intermediate Similarity NPC49088
0.7083 Intermediate Similarity NPC214584
0.7083 Intermediate Similarity NPC26906
0.7021 Intermediate Similarity NPC17810
0.6957 Remote Similarity NPC323445
0.6939 Remote Similarity NPC71506
0.6939 Remote Similarity NPC177112
0.6875 Remote Similarity NPC163984
0.6875 Remote Similarity NPC58970
0.6875 Remote Similarity NPC176819
0.6875 Remote Similarity NPC32351
0.6863 Remote Similarity NPC469770
0.6842 Remote Similarity NPC151719
0.6842 Remote Similarity NPC66577
0.6818 Remote Similarity NPC193180
0.68 Remote Similarity NPC476679
0.68 Remote Similarity NPC268564
0.6757 Remote Similarity NPC138113
0.6757 Remote Similarity NPC123965
0.6757 Remote Similarity NPC115959
0.6744 Remote Similarity NPC78551
0.6744 Remote Similarity NPC227632
0.6744 Remote Similarity NPC62086
0.6667 Remote Similarity NPC5626
0.6604 Remote Similarity NPC475696
0.6604 Remote Similarity NPC474415
0.6604 Remote Similarity NPC470370
0.6604 Remote Similarity NPC474528
0.6604 Remote Similarity NPC470369
0.66 Remote Similarity NPC294358
0.66 Remote Similarity NPC40417
0.6591 Remote Similarity NPC103290
0.6591 Remote Similarity NPC188596
0.6579 Remote Similarity NPC60288
0.6538 Remote Similarity NPC232247
0.6538 Remote Similarity NPC123194
0.6538 Remote Similarity NPC148163
0.6538 Remote Similarity NPC130209
0.6538 Remote Similarity NPC251666
0.6538 Remote Similarity NPC470893
0.6538 Remote Similarity NPC148216
0.6531 Remote Similarity NPC26960
0.6531 Remote Similarity NPC182102
0.6481 Remote Similarity NPC469769
0.6471 Remote Similarity NPC14002
0.6471 Remote Similarity NPC23117
0.6458 Remote Similarity NPC178644
0.6415 Remote Similarity NPC141699
0.6415 Remote Similarity NPC473733
0.64 Remote Similarity NPC27438
0.6389 Remote Similarity NPC287191
0.6389 Remote Similarity NPC31891
0.6389 Remote Similarity NPC266144
0.6389 Remote Similarity NPC266539
0.6383 Remote Similarity NPC24824
0.6383 Remote Similarity NPC165651
0.6383 Remote Similarity NPC210560
0.6364 Remote Similarity NPC474420
0.6364 Remote Similarity NPC246165
0.6364 Remote Similarity NPC472304
0.6364 Remote Similarity NPC474454
0.6364 Remote Similarity NPC474455
0.6364 Remote Similarity NPC475716
0.6364 Remote Similarity NPC276764
0.6346 Remote Similarity NPC100809
0.6346 Remote Similarity NPC209431
0.6341 Remote Similarity NPC182392
0.6327 Remote Similarity NPC106990
0.6316 Remote Similarity NPC34671
0.6296 Remote Similarity NPC474457
0.6296 Remote Similarity NPC165808
0.625 Remote Similarity NPC8610
0.625 Remote Similarity NPC22098
0.625 Remote Similarity NPC276009
0.625 Remote Similarity NPC159420
0.625 Remote Similarity NPC262558
0.625 Remote Similarity NPC195246
0.6226 Remote Similarity NPC298299
0.6222 Remote Similarity NPC473614
0.6216 Remote Similarity NPC10183
0.62 Remote Similarity NPC329773
0.6182 Remote Similarity NPC56905
0.6182 Remote Similarity NPC27610
0.6154 Remote Similarity NPC295777
0.6154 Remote Similarity NPC69898
0.614 Remote Similarity NPC469728
0.614 Remote Similarity NPC194208
0.614 Remote Similarity NPC282694
0.614 Remote Similarity NPC79576
0.6122 Remote Similarity NPC100445
0.6111 Remote Similarity NPC88325
0.6111 Remote Similarity NPC249645
0.6111 Remote Similarity NPC55412
0.6111 Remote Similarity NPC38513
0.6098 Remote Similarity NPC305759
0.6098 Remote Similarity NPC62779
0.6098 Remote Similarity NPC173592
0.6098 Remote Similarity NPC99088
0.6078 Remote Similarity NPC64866
0.6053 Remote Similarity NPC262789
0.6053 Remote Similarity NPC179103
0.6053 Remote Similarity NPC64176
0.6053 Remote Similarity NPC138325
0.6053 Remote Similarity NPC288991
0.6053 Remote Similarity NPC76765
0.6042 Remote Similarity NPC166788
0.6038 Remote Similarity NPC202850
0.6038 Remote Similarity NPC63396
0.6034 Remote Similarity NPC145715
0.6034 Remote Similarity NPC165695
0.6034 Remote Similarity NPC174956
0.6 Remote Similarity NPC22019
0.6 Remote Similarity NPC281986
0.6 Remote Similarity NPC321568
0.6 Remote Similarity NPC208749
0.6 Remote Similarity NPC115385
0.6 Remote Similarity NPC11130
0.6 Remote Similarity NPC234597
0.5965 Remote Similarity NPC66020
0.5965 Remote Similarity NPC317778
0.5965 Remote Similarity NPC135648
0.5965 Remote Similarity NPC127582
0.5965 Remote Similarity NPC19241
0.5965 Remote Similarity NPC240506
0.5965 Remote Similarity NPC176621
0.5965 Remote Similarity NPC311809
0.5962 Remote Similarity NPC68014
0.5962 Remote Similarity NPC208638
0.5957 Remote Similarity NPC106819
0.5957 Remote Similarity NPC269862
0.5957 Remote Similarity NPC51762
0.5957 Remote Similarity NPC141777
0.5957 Remote Similarity NPC23145
0.5957 Remote Similarity NPC474118
0.5957 Remote Similarity NPC227670
0.5957 Remote Similarity NPC90803
0.5957 Remote Similarity NPC90506
0.5957 Remote Similarity NPC166362
0.5932 Remote Similarity NPC475124
0.5932 Remote Similarity NPC285371
0.5932 Remote Similarity NPC6697
0.5932 Remote Similarity NPC473959
0.5932 Remote Similarity NPC469662
0.5926 Remote Similarity NPC223604
0.5926 Remote Similarity NPC275472
0.5918 Remote Similarity NPC236355
0.5918 Remote Similarity NPC4079
0.5918 Remote Similarity NPC14917
0.5893 Remote Similarity NPC60772
0.5893 Remote Similarity NPC170799
0.5893 Remote Similarity NPC311852
0.5893 Remote Similarity NPC308108
0.5882 Remote Similarity NPC289388

  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 NPC139717 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
0.9714 High Similarity NPD319 Phase 1
0.7209 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD8262 Approved
0.6538 Remote Similarity NPD342 Phase 1
0.6111 Remote Similarity NPD4219 Approved
0.5893 Remote Similarity NPD287 Approved
0.5862 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