Natural Product: NPC300943

Natural Product IDNPC300943
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 5,6,3'-Trihydroxy-3,7,4'-Trimethoxyflavone
IUPAC Name 5,6-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1085428
PubChem CID 442621
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

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 UQBUUCDVKDSHCE-UHFFFAOYSA-N
Standard InCHI InChI=1S/C18H16O8/c1-23-10-5-4-8(6-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3
SMILES COc1ccc(cc1O)c1oc2cc(OC)c(c(c2c(=O)c1OC)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   360.08 Volume:   343.445
?
Van der Waals volume.
Dense:   1.048 LogP:   1.978
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.005
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.802
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   18.0
TPSA:   118.59
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   3.0 Rings:   3.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.608 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.506 Fsp3:   0.167
MCE-18:   20.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.403 Fluc inhibitor:   0.437
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.862
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.632
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.377 Promiscuous compounds:   0.803

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.201 MDCK Permeability:   -4.797
Pgp-inhibitor:   0.691 Pgp-substrate:   0.088
PAMPA:   0.36
?
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):   0.316
20% Bioavailability (F20%):   0.125 30% Bioavailability (F30%):   0.523
50% Bioavailability (F50%):   0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.002 MRP1:   0.94
Plasma Protein Binding (PPB):   96.432% Volume Distribution (VD):   -0.593
Fu: 3.332%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.565
OATP1B3 inhibitor:   0.994 BCRP inhibitor:   0.984
BSEP inhibitor:   0.909

ADMET: Metabolism

CYP1A2-inhibitor:   0.466 CYP1A2-substrate:   0.02
CYP2C19-inhibitor:   0.004 CYP2C19-substrate:   0.469
CYP2C9-inhibitor:   0.529 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.508 CYP2D6-substrate:   0.194
CYP3A4-inhibitor:   0.003 CYP3A4-substrate:   0.023
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.969
HLM stability:   0.888
?
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):  5.495 Half-life (T1/2):  2.014

ADMET: Toxicity

hERG Blockers:  0.082 hERG Blockers (10um):  0.513
Human Hepatotoxicity (H-HT):  0.393 Drug-induced Liver Injury (DILI):  0.74
AMES Toxicity:  0.466 Rat Oral Acute Toxicity:  0.341
Maximum Recommended Daily Dose:  0.412 Skin Sensitization:  0.725
Carcinogencity:  0.721 Eye Corrosion:  0.43
Eye Irritation:  0.98 Respiratory Toxicity:  0.667
Drug-induced Neurotoxicity:  0.139 Ototoxicity:  0.204
Hematotoxicity:  0.203 Drug-induced Nephrotoxicity:  0.126
Genotoxicity:  0.327 RPMI-8226 Immunitoxicity:  0.08
A549 Cytotoxicity:  0.268 Hek293 Cytotoxicity:  0.314
BCF:   0.844
?
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:   3.452
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.442
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.972
?
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
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[12608858]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO23263 Crinum yemense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[15270564]
NPO23510 Vicia faba Species Fabaceae Eukaryota flowers n.a. n.a. PMID[16180811]
NPO14937 Gelonium aequoreum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[17714747]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota aerial parts n.a. n.a. PMID[19299148]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota Whole Plant Tawangmangu village, Karanganyar, Central Java, Indonesia 2003-FEB PMID[19422206]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[19422206]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota leaves Guangxi Province, China 2000-JAN PMID[22040053]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota n.a. leaf n.a. PMID[22040053]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22210168]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. stem n.a. PMID[22210168]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23282042]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[2691636]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2691636]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[28099005]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[39355945]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[7807120]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. root n.a. PMID[8945774]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO845 Cyrtanthus obliquus Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14937 Gelonium aequoreum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16719 Alluaudia dumosa Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15464 Argylia radiata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9482 Durio kutejensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11989 Erythrostemon gilliesii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5874 Fumago vagans n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16231 Helichrysum acutatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3903 Hemizonia congesta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16558 Mallotus stenanthus Species Salangidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5195.1 Odontites vernus subsp. serotinus Subspecies Orobanchaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10679 Scutellaria nepetoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14473 Stellaria delavayi Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24279 Streptomyces inusitatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO14140 Vernonia arbor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13988 Westiella intricata Species Hapalosiphonaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23427 Becium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO18884 Apuleia leiocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23263 Crinum yemense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23107 Adiantum monochlamys Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23562 Pachyphragma macrophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23510 Vicia faba Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23107 Adiantum monochlamys Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5195.1 Odontites vernus subsp. serotinus Subspecies Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16558 Mallotus stenanthus Species Salangidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14937 Gelonium aequoreum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13731 Centaurea webbiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13988 Westiella intricata Species Hapalosiphonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6943 Vernonanthura chamaedrys Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14140 Vernonia arbor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20857 Commiphora erythraea Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9482 Durio kutejensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15464 Argylia radiata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23107 Adiantum monochlamys Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO845 Cyrtanthus obliquus Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23562 Pachyphragma macrophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5874 Fumago vagans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10679 Scutellaria nepetoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14473 Stellaria delavayi Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23263 Crinum yemense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16719 Alluaudia dumosa Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11989 Erythrostemon gilliesii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24279 Streptomyces inusitatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3903 Hemizonia congesta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16231 Helichrysum acutatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5195.1 Odontites vernus subsp. serotinus Subspecies Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23648 Spilanthes mauritiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23427 Becium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18884 Apuleia leiocarpa Species Fabaceae 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
NPT163 Individual protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens ED50 > 50.0 uM PMID[19422206]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell line HT-29 Homo sapiens ED50 = 3.6 uM PMID[19422206]
NPT139 Cell line HT-29 Homo sapiens ED50 = 310.0 nM PMID[19422206]

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 NPC300943 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
0.7925 Intermediate Similarity NPC305663
0.7547 Intermediate Similarity NPC43243
0.7455 Intermediate Similarity NPC270620
0.7321 Intermediate Similarity NPC25495
0.7321 Intermediate Similarity NPC18607
0.7143 Intermediate Similarity NPC212678
0.6964 Remote Similarity NPC9609
0.6964 Remote Similarity NPC603827
0.6842 Remote Similarity NPC82325
0.6552 Remote Similarity NPC605582
0.6271 Remote Similarity NPC204854
0.6167 Remote Similarity NPC4481
0.6167 Remote Similarity NPC603112
0.6034 Remote Similarity NPC262094
0.5932 Remote Similarity NPC57030
0.5738 Remote Similarity NPC265511
0.5667 Remote Similarity NPC214138
0.5667 Remote Similarity NPC110070
0.5667 Remote Similarity NPC188871
0.5645 Remote Similarity NPC236769
0.5645 Remote Similarity NPC283600
0.5574 Remote Similarity NPC162313
0.5574 Remote Similarity NPC18772
0.5556 Remote Similarity NPC78326
0.55 Remote Similarity NPC203891
0.55 Remote Similarity NPC275722
0.55 Remote Similarity NPC103904
0.5484 Remote Similarity NPC176300
0.5484 Remote Similarity NPC200740
0.541 Remote Similarity NPC59951
0.541 Remote Similarity NPC198826
0.541 Remote Similarity NPC146679
0.541 Remote Similarity NPC163524
0.541 Remote Similarity NPC610660
0.5397 Remote Similarity NPC93376
0.5397 Remote Similarity NPC58382
0.5397 Remote Similarity NPC160951
0.5397 Remote Similarity NPC223579
0.5397 Remote Similarity NPC206604
0.5395 Remote Similarity NPC21666
0.5385 Remote Similarity NPC485299
0.5312 Remote Similarity NPC261004
0.5263 Remote Similarity NPC611303
0.5246 Remote Similarity NPC123886
0.5238 Remote Similarity NPC115798
0.5224 Remote Similarity NPC99671
0.5161 Remote Similarity NPC286342
0.5161 Remote Similarity NPC76376
0.5161 Remote Similarity NPC101830
0.5156 Remote Similarity NPC75215
0.5156 Remote Similarity NPC603596
0.5156 Remote Similarity NPC608258
0.5082 Remote Similarity NPC607530
0.5079 Remote Similarity NPC100916
0.5079 Remote Similarity NPC256283
0.5077 Remote Similarity NPC279989
0.5075 Remote Similarity NPC76482

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC300943 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