Natural Product: NPC8981

Natural Product IDNPC8981
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 5'-(3-Buten-1-Ynyl)-2,2'-Bithiophene
IUPAC Name 2-but-3-en-1-ynyl-5-thiophen-2-ylthiophene
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2252901
PubChem CID 70813
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002021] Bi- and oligothiophenes

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey GWAIEOFEEWQORO-UHFFFAOYSA-N
Standard InCHI InChI=1S/C12H8S2/c1-2-3-5-10-7-8-12(14-10)11-6-4-9-13-11/h2,4,6-9H,1H2
SMILES C=CC#Cc1ccc(c2cccs2)s1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   216.01 Volume:   217.558
?
Van der Waals volume.
Dense:   0.993 LogP:   4.72
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.389
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -5.249
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   12.0
TPSA:   0.0
?
Topological Polar Surface Area.
 H-Bond Acceptor:   0.0
H-Bond Donor:   0.0 Rings:   2.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.632 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.999 Fsp3:   0.0
MCE-18:   9.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.3 Fluc inhibitor:   0.97
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.483
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.699
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.921 Promiscuous compounds:   0.019

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.515 MDCK Permeability:   -4.624
Pgp-inhibitor:   0.291 Pgp-substrate:   0.0
PAMPA:   0.06
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.048
20% Bioavailability (F20%):   0.891 30% Bioavailability (F30%):   0.854
50% Bioavailability (F50%):   0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.042 MRP1:   0.09
Plasma Protein Binding (PPB):   97.326% Volume Distribution (VD):   0.367
Fu: 1.87%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.425
OATP1B3 inhibitor:   0.823 BCRP inhibitor:   0.1
BSEP inhibitor:   0.994

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.892
CYP2C19-inhibitor:   0.78 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   1.0 CYP2C9-substrate:   0.012
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   0.961
CYP3A4-inhibitor:   0.016 CYP3A4-substrate:   0.106
CYP2B6-substrate:   0.028 CYP2C8-inhibitor:   1.0
HLM stability:   0.001
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  6.316 Half-life (T1/2):  0.585

ADMET: Toxicity

hERG Blockers:  0.365 hERG Blockers (10um):  0.609
Human Hepatotoxicity (H-HT):  0.8 Drug-induced Liver Injury (DILI):  1.0
AMES Toxicity:  0.764 Rat Oral Acute Toxicity:  0.7
Maximum Recommended Daily Dose:  0.461 Skin Sensitization:  0.821
Carcinogencity:  0.803 Eye Corrosion:  0.997
Eye Irritation:  0.993 Respiratory Toxicity:  0.998
Drug-induced Neurotoxicity:  0.385 Ototoxicity:  0.512
Hematotoxicity:  0.033 Drug-induced Nephrotoxicity:  0.265
Genotoxicity:  0.972 RPMI-8226 Immunitoxicity:  0.04
A549 Cytotoxicity:  0.011 Hek293 Cytotoxicity:  0.691
BCF:   1.63
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.687
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.855
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.614
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1155/2014/726070]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[17011103]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO23021 Solanum congestiflorum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[21905650]
NPO1672 Apostichopus japonicus Species Stichopodidae Eukaryota n.a. n.a. n.a. PMID[22700234]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[25700090]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[39181940]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[39716808]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15546 Herba ecliptae prostratae n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO17904 Cassia renigera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18770 Euphausia pacifica Species Euphausiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18931 Buellia canescens Species Caliciaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23021 Solanum congestiflorum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1672 Apostichopus japonicus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18678 Actinomadura pelletieri Species Thermomonosporaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO18266 Microsphaeropsis olivacea Species n.a. Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10392 Strychnos soubrensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21183 Peziza mollissima Species Pezizaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21011 Ormosia amazonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18882 Chondrococcus hornemannii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO17639 Stevia achalensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4947 Tagetes minuta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3608 Eleutherococcus giraldii Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20606 Piper tuberculatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota Roots n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4947 Tagetes minuta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20606 Piper tuberculatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20606 Piper tuberculatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4947 Tagetes minuta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3608 Eleutherococcus giraldii Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15546 Herba ecliptae prostratae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1672 Apostichopus japonicus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4163 Echinopsis latifolius Species Cactaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22699 Echinops setifer Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10392 Strychnos soubrensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28696 Rhaponticum uniflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17639 Stevia achalensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18678 Actinomadura pelletieri Species Thermomonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3608 Eleutherococcus giraldii Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18770 Euphausia pacifica Species Euphausiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4947 Tagetes minuta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21011 Ormosia amazonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21183 Peziza mollissima Species Pezizaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17904 Cassia renigera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20606 Piper tuberculatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4597 Campanula lactiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23021 Solanum congestiflorum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1672 Apostichopus japonicus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17357 Bactrocera kraussi Species Tephritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18266 Microsphaeropsis olivacea Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18931 Buellia canescens Species Caliciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18882 Chondrococcus hornemannii n.a. n.a. n.a. 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana IC50 > 50000.0 nM PMID[16506815]
NPT637 Organism Fusarium oxysporum Fusarium oxysporum GI = 96.0 % PMID[16506815]
NPT637 Organism Fusarium oxysporum Fusarium oxysporum IC50 > 50000.0 nM PMID[16506815]
NPT852 Organism Phomopsis obscurans Phomopsis obscurans IC50 > 50000.0 nM PMID[16506815]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae IC50 = 46000.0 nM PMID[16506815]
NPT1096 Organism Colletotrichum acutatum Colletotrichum acutatum IC50 = 28500.0 nM PMID[16506815]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae IC50 = 28000.0 nM PMID[16506815]
NPT1096 Organism Colletotrichum acutatum Colletotrichum acutatum IC50 = 7600.0 nM PMID[16506815]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 96.0 % PMID[16506815]
NPT1095 Organism Plasmopara viticola Plasmopara viticola IC50 = 22000.0 nM PMID[16506815]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides IC50 = 10200.0 nM PMID[16506815]
NPT1095 Organism Plasmopara viticola Plasmopara viticola IC50 = 19500.0 nM PMID[16506815]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides IC50 = 4200.0 nM PMID[16506815]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC8981 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.675 Remote Similarity NPC602091
0.5122 Remote Similarity NPC173019

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC8981 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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