Natural Product: NPC180340

Natural Product IDNPC180340
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Dehydrodeguelin
IUPAC Name n.a.
Synonyms Dehydrodeguelin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL465673
PubChem CID 3083803
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0001607] Rotenoids
          • [CHEMONTID:0003528] Rotenones

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 NGQVFILFHVPLFE-UHFFFAOYSA-N
Standard InCHI InChI=1S/C23H20O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10H,11H2,1-4H3
SMILES COc1cc2c(cc1OC)OCc1c2c(=O)c2c(o1)c1C=CC(Oc1cc2)(C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   392.13 Volume:   392.595
?
Van der Waals volume.
Dense:   0.999 LogP:   3.557
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.284
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -5.418
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   27.0
TPSA:   67.13
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   0.0 Rings:   5.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.637 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.056 Fsp3:   0.261
MCE-18:   62.0
?
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:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.643 Fluc inhibitor:   0.341
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.791
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.637
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.165 Promiscuous compounds:   0.3

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.771 MDCK Permeability:   -4.739
Pgp-inhibitor:   0.968 Pgp-substrate:   0.031
PAMPA:   0.071
?
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):   0.04
20% Bioavailability (F20%):   0.22 30% Bioavailability (F30%):   0.386
50% Bioavailability (F50%):   0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.075 MRP1:   0.791
Plasma Protein Binding (PPB):   97.223% Volume Distribution (VD):   0.14
Fu: 2.036%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.994
OATP1B3 inhibitor:   0.998 BCRP inhibitor:   0.978
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.377 CYP1A2-substrate:   0.986
CYP2C19-inhibitor:   0.501 CYP2C19-substrate:   0.927
CYP2C9-inhibitor:   0.935 CYP2C9-substrate:   0.039
CYP2D6-inhibitor:   0.285 CYP2D6-substrate:   0.983
CYP3A4-inhibitor:   0.563 CYP3A4-substrate:   0.969
CYP2B6-substrate:   0.001 CYP2C8-inhibitor:   0.992
HLM stability:   0.7
?
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):  5.749 Half-life (T1/2):  1.127

ADMET: Toxicity

hERG Blockers:  0.172 hERG Blockers (10um):  0.486
Human Hepatotoxicity (H-HT):  0.703 Drug-induced Liver Injury (DILI):  0.971
AMES Toxicity:  0.726 Rat Oral Acute Toxicity:  0.56
Maximum Recommended Daily Dose:  0.626 Skin Sensitization:  0.372
Carcinogencity:  0.968 Eye Corrosion:  0.006
Eye Irritation:  0.728 Respiratory Toxicity:  0.774
Drug-induced Neurotoxicity:  0.392 Ototoxicity:  0.319
Hematotoxicity:  0.411 Drug-induced Nephrotoxicity:  0.296
Genotoxicity:  0.469 RPMI-8226 Immunitoxicity:  0.157
A549 Cytotoxicity:  0.08 Hek293 Cytotoxicity:  0.41
BCF:   1.683
?
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:   4.287
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.354
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.422
?
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
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. DOI[10.1021/np50028a032]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10814365]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. PMID[10993241]
NPO32669 derris malaccensis plain Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11975515]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16644212]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18841906]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO8274 Geijera parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[23848189]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[24684844]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[26434122]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26476665]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota Fruits n.a. n.a. PMID[28075580]
NPO5368 Achillea cretica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[36408972]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8326318]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8350086]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[8759159]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. PMID[8759159]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9322358]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[9834152]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5368 Achillea cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12750 Cordia americana Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2671 Pedicularis semitorta Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO439 Luffa operculata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8274 Geijera parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa 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]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6147 Eupatorium riparium 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]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO439 Luffa operculata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1007 Crotalaria paniculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21911 Tephrosia purpurea Species Fabaceae 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]
NPO16886 Amorpha fruticosa Species Fabaceae 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]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30657 Lndigofera tinctoria n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae 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]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12750 Cordia americana Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15101 Tricholoma panaeolum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO439 Luffa operculata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8274 Geijera parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5368 Achillea cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2671 Pedicularis semitorta Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1007 Crotalaria paniculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4520 Allium macrostemon Species Amaryllidaceae 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 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
NPT1864 Cell line L5178Y Mus musculus IC50 = 10200.0 nM PMID[28075580]
NPT319 Cell line B16 Mus musculus IC50 = 560.0 nM PMID[28665590]
NPT65 Cell line HepG2 Homo sapiens IC50 = 560.0 nM PMID[28665590]
NPT451 Organism Helicobacter pylori Helicobacter pylori MIC = 4.0 ug.mL-1 PMID[11975515]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 500000.0 nM PMID[23186287]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 1200.0 nM PMID[26467198]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 80000.0 nM PMID[26467198]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. GI = 40.0 % PMID[26467198]

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 NPC180340 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
0.7432 Intermediate Similarity NPC40037
0.6438 Remote Similarity NPC128961
0.641 Remote Similarity NPC19097
0.5904 Remote Similarity NPC604547
0.5696 Remote Similarity NPC273021
0.5625 Remote Similarity NPC248299
0.5385 Remote Similarity NPC604955
0.5065 Remote Similarity NPC607923

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC180340 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