Natural Product: NPC490411

Natural Product IDNPC490411
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Procyanidin B5
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID n.a.
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 GMISZFQPFDAPGI-WXXMRKNTSA-N
Standard InCHI InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21?,26-,28-,29+,30-/m1/s1
SMILES OC1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C=C1)=C2O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   578.14 Volume:   549.942
?
Van der Waals volume.
Dense:   1.051 LogP:   1.088
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.564
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.192
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   34.0
TPSA:   220.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   12.0
H-Bond Donor:   10.0 Rings:   6.0
Heavy Atoms:   12.0

MedChem Properties

QED Drug-Likeness Score:   0.159 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.527 Fsp3:   0.2
MCE-18:   126.667
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Accepted BMS Rule:   1
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.829 Fluc inhibitor:   0.252
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.252
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.461
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.563 Promiscuous compounds:   0.207

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -7.135 MDCK Permeability:   -4.919
Pgp-inhibitor:   0.0 Pgp-substrate:   0.047
PAMPA:   0.315
?
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):   0.006
20% Bioavailability (F20%):   0.997 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.007 MRP1:   0.845
Plasma Protein Binding (PPB):   92.226% Volume Distribution (VD):   0.216
Fu: 15.58%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.992
OATP1B3 inhibitor:   0.997 BCRP inhibitor:   0.062
BSEP inhibitor:   0.001

ADMET: Metabolism

CYP1A2-inhibitor:   1.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.023 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   1.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.999
HLM stability:   0.0
?
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):  10.695 Half-life (T1/2):  3.379

ADMET: Toxicity

hERG Blockers:  0.12 hERG Blockers (10um):  0.844
Human Hepatotoxicity (H-HT):  0.926 Drug-induced Liver Injury (DILI):  0.568
AMES Toxicity:  0.506 Rat Oral Acute Toxicity:  0.685
Maximum Recommended Daily Dose:  0.975 Skin Sensitization:  1.0
Carcinogencity:  0.016 Eye Corrosion:  0.0
Eye Irritation:  0.812 Respiratory Toxicity:  0.905
Drug-induced Neurotoxicity:  0.015 Ototoxicity:  0.958
Hematotoxicity:  0.017 Drug-induced Nephrotoxicity:  0.137
Genotoxicity:  1.0 RPMI-8226 Immunitoxicity:  0.039
A549 Cytotoxicity:  0.998 Hek293 Cytotoxicity:  0.973
BCF:   1.066
?
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:   3.469
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.726
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.134
?
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
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[ 16712885]
NPO15336 Prunus avium Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1016/j.foodchem.2007.08.004]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO15336 Prunus avium Species Rosaceae Eukaryota n.a. fruit n.a. DOI[10.1016/j.phytochem.2007.01.008]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1021/jf970571j]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. stem n.a. DOI[10.1021/np50053a043]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. kernel n.a. PMID[12232058]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO15336 Prunus avium Species Rosaceae Eukaryota n.a. fruit n.a. PMID[17328933]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. fruit n.a. PMID[21648406]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. fruit n.a. PMID[240326]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[37255739]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[38279238]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. kernel n.a. PMID[7092570]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8277309]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15336 Prunus avium Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5019 Mespilus germanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7546 Prunus domestica Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7546 Prunus domestica Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO5019 Mespilus germanica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15336 Prunus avium Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15336 Prunus avium Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO7546 Prunus domestica Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15336 Prunus avium Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5019 Mespilus germanica Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7546 Prunus domestica Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5019 Mespilus germanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15336 Prunus avium Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7546 Prunus domestica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[USDA]

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
NPO14992 Prunus persica Raw n.a. 0.039999999 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO15336 Prunus avium Raw n.a. 0.200000008 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO16230 Malus pumila n.a. n.a. 0.967499996 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO25145 Cydonia oblonga Other n.a. 0.119999995 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO366 Pyrus communis Raw n.a. 0.005 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO5019 Mespilus germanica Other n.a. 0.029999999 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO7546 Prunus domestica Raw n.a. 1.589999994 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO8258 Camellia sinensis Tea Or Coffee n.a. 0.01 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO9632 Annona reticulata Raw n.a. 0.820000013 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

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

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 NPC490411 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
1.0 High Similarity NPC294558
1.0 High Similarity NPC18185
1.0 High Similarity NPC263940
0.918 High Similarity NPC226809
0.7619 Intermediate Similarity NPC58190
0.7619 Intermediate Similarity NPC82917
0.7619 Intermediate Similarity NPC108811
0.7619 Intermediate Similarity NPC170103
0.7619 Intermediate Similarity NPC236202
0.7619 Intermediate Similarity NPC262911
0.7619 Intermediate Similarity NPC202742
0.75 Intermediate Similarity NPC246202
0.75 Intermediate Similarity NPC224161
0.75 Intermediate Similarity NPC46335
0.75 Intermediate Similarity NPC279406
0.75 Intermediate Similarity NPC486519
0.7458 Intermediate Similarity NPC178054
0.7432 Intermediate Similarity NPC478340
0.6974 Remote Similarity NPC78074
0.6897 Remote Similarity NPC261619
0.6897 Remote Similarity NPC61477
0.6897 Remote Similarity NPC78770
0.6897 Remote Similarity NPC219876
0.6897 Remote Similarity NPC126029
0.6897 Remote Similarity NPC15658
0.6761 Remote Similarity NPC278548
0.6625 Remote Similarity NPC159526
0.6522 Remote Similarity NPC313116
0.6522 Remote Similarity NPC603340
0.6456 Remote Similarity NPC478337
0.6456 Remote Similarity NPC478338
0.6338 Remote Similarity NPC70409
0.6338 Remote Similarity NPC204770
0.6338 Remote Similarity NPC600551
0.6338 Remote Similarity NPC601980
0.6338 Remote Similarity NPC602065
0.6338 Remote Similarity NPC611024
0.6269 Remote Similarity NPC96576
0.6203 Remote Similarity NPC86630
0.6164 Remote Similarity NPC600630
0.6164 Remote Similarity NPC607896
0.6164 Remote Similarity NPC611369
0.6154 Remote Similarity NPC147743
0.6154 Remote Similarity NPC4809
0.6154 Remote Similarity NPC73517
0.6125 Remote Similarity NPC106601
0.6125 Remote Similarity NPC151474
0.6049 Remote Similarity NPC212614
0.6049 Remote Similarity NPC205613
0.5946 Remote Similarity NPC272552
0.5946 Remote Similarity NPC226108
0.5946 Remote Similarity NPC322899
0.5867 Remote Similarity NPC46283
0.5867 Remote Similarity NPC469944
0.5811 Remote Similarity NPC211561
0.5789 Remote Similarity NPC44192
0.5738 Remote Similarity NPC207179
0.5738 Remote Similarity NPC167571
0.5738 Remote Similarity NPC278552
0.5658 Remote Similarity NPC302549
0.5641 Remote Similarity NPC478616
0.5641 Remote Similarity NPC478339
0.5634 Remote Similarity NPC601999
0.56 Remote Similarity NPC601997
0.56 Remote Similarity NPC609211
0.56 Remote Similarity NPC610665
0.5517 Remote Similarity NPC478617
0.5513 Remote Similarity NPC20050
0.5484 Remote Similarity NPC268266
0.5484 Remote Similarity NPC42760
0.5484 Remote Similarity NPC220825
0.5484 Remote Similarity NPC268342
0.5455 Remote Similarity NPC134911
0.5443 Remote Similarity NPC306267
0.5405 Remote Similarity NPC28440
0.5375 Remote Similarity NPC135021
0.5323 Remote Similarity NPC601844
0.527 Remote Similarity NPC184245
0.527 Remote Similarity NPC187801
0.527 Remote Similarity NPC610920
0.5181 Remote Similarity NPC9309
0.5147 Remote Similarity NPC16435
0.5147 Remote Similarity NPC171932
0.5132 Remote Similarity NPC155564
0.5122 Remote Similarity NPC471404
0.5075 Remote Similarity NPC36835
0.5075 Remote Similarity NPC246162
0.5075 Remote Similarity NPC9743
0.5075 Remote Similarity NPC260491
0.5075 Remote Similarity NPC61506
0.5075 Remote Similarity NPC240476

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC490411 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
0.6897 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6897 Remote Similarity NPD1613 Phase 4

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