Natural Product: NPC239608

Natural Product IDNPC239608
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (-)-Evofolin B
IUPAC Name (2S)-3-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)propan-1-one
Synonyms (-)-Evofolin B
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL602133
PubChem CID 46229015
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

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 QMYGRGKKZBRZKH-GFCCVEGCSA-N
Standard InCHI InChI=1S/C17H18O6/c1-22-15-7-10(3-5-13(15)19)12(9-18)17(21)11-4-6-14(20)16(8-11)23-2/h3-8,12,18-20H,9H2,1-2H3/t12-/m1/s1
SMILES OC[C@@H](C(=O)c1ccc(c(c1)OC)O)c1ccc(c(c1)OC)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   318.11 Volume:   319.761
?
Van der Waals volume.
Dense:   0.995 LogP:   1.169
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.512
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.13
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   6.0 Rigid Bonds:   13.0
TPSA:   96.22
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   3.0 Rings:   2.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.706 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.675 Fsp3:   0.235
MCE-18:   28.0
?
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:   0
Colloidal aggregators:   0.197 Fluc inhibitor:   0.703
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.041
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.288
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.395 Promiscuous compounds:   0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.103 MDCK Permeability:   -4.83
Pgp-inhibitor:   0.024 Pgp-substrate:   0.091
PAMPA:   0.444
?
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%):   0.116 30% Bioavailability (F30%):   0.278
50% Bioavailability (F50%):   0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.605
Plasma Protein Binding (PPB):   62.689% Volume Distribution (VD):   -0.043
Fu: 38.586%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.802
BSEP inhibitor:   0.285

ADMET: Metabolism

CYP1A2-inhibitor:   0.039 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.005 CYP2C19-substrate:   0.013
CYP2C9-inhibitor:   0.763 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.923 CYP2D6-substrate:   0.126
CYP3A4-inhibitor:   0.02 CYP3A4-substrate:   0.024
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.493
HLM stability:   0.067
?
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):  8.785 Half-life (T1/2):  1.541

ADMET: Toxicity

hERG Blockers:  0.089 hERG Blockers (10um):  0.206
Human Hepatotoxicity (H-HT):  0.695 Drug-induced Liver Injury (DILI):  0.31
AMES Toxicity:  0.244 Rat Oral Acute Toxicity:  0.116
Maximum Recommended Daily Dose:  0.365 Skin Sensitization:  0.973
Carcinogencity:  0.087 Eye Corrosion:  0.025
Eye Irritation:  0.971 Respiratory Toxicity:  0.873
Drug-induced Neurotoxicity:  0.436 Ototoxicity:  0.447
Hematotoxicity:  0.262 Drug-induced Nephrotoxicity:  0.502
Genotoxicity:  0.413 RPMI-8226 Immunitoxicity:  0.076
A549 Cytotoxicity:  0.194 Hek293 Cytotoxicity:  0.317
BCF:   0.85
?
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:   3.224
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.04
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.59
?
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
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[12643908]
NPO21341 Morus macroura Species Moraceae Eukaryota n.a. stem n.a. PMID[15467233]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota Leaves n.a. n.a. PMID[17637068]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[18302336]
NPO22421 Microtropis japonica Species Celastraceae Eukaryota stem n.a. n.a. PMID[18471021]
NPO22421 Microtropis japonica Species Celastraceae Eukaryota n.a. stem n.a. PMID[18471021]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. whole plant n.a. PMID[18771268]
NPO22421 Microtropis japonica Species Celastraceae Eukaryota Stems n.a. n.a. PMID[19534471]
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[20189399]
NPO10464 Epipedobates anthonyi Species Dendrobatidae Eukaryota n.a. n.a. n.a. PMID[20337496]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[21131198]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22432912]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[26724423]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[26724423]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[32004936]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[39053741]
NPO23441 Schisandra sphaerandra Species Schisandraceae Eukaryota n.a. stem n.a. PMID[8778243]
NPO21610 Laurencia rigida Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[9358636]
NPO20787 Achyranthes aspera Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1109 Corydalis persica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22272 Raphanus raphanistrum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21341 Morus macroura Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6425 Betula davurica Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22421 Microtropis japonica Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22788 Barnettia kerrii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3277 Salix alba Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21776 Sesbania grandiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21610 Laurencia rigida Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22212 Rhizophora mangle Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21341 Morus macroura Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20787 Achyranthes aspera Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21341 Morus macroura Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20787 Achyranthes aspera Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23441 Schisandra sphaerandra Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5933 Drimia fugax Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21610 Laurencia rigida Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14938 Cybister lateralimarginalis Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22212 Rhizophora mangle Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20787 Achyranthes aspera Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6425 Betula davurica Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22788 Barnettia kerrii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10464 Epipedobates anthonyi Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19561 Garcinia conrauana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22421 Microtropis japonica Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22670 Phebalium bilobum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23441 Schisandra sphaerandra Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22915 Stereocaulon azoreum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22272 Raphanus raphanistrum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21341 Morus macroura Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17102 Ocypus olens Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3277 Salix alba Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22734 Neopringlea integrifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5933 Drimia fugax Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1109 Corydalis persica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21776 Sesbania grandiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4554 Isatis tinctoria Species Brassicaceae 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
NPT2 Others Unspecified n.a. Inhibition = 18.2 % PMID[20189399]
NPT2 Others Unspecified n.a. Inhibition = 15.0 % PMID[20189399]
NPT2 Others Unspecified n.a. Inhibition = 16.4 % PMID[20189399]
NPT2 Others Unspecified n.a. Inhibition = 23.5 % PMID[20189399]

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 NPC239608 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 NPC46161
0.8537 High Similarity NPC474903
0.6667 Remote Similarity NPC604189
0.6585 Remote Similarity NPC139519
0.625 Remote Similarity NPC32163
0.6136 Remote Similarity NPC50763
0.6136 Remote Similarity NPC325625
0.587 Remote Similarity NPC165045
0.587 Remote Similarity NPC118533
0.5814 Remote Similarity NPC16651
0.5238 Remote Similarity NPC203719
0.5227 Remote Similarity NPC160380
0.5227 Remote Similarity NPC38996
0.5116 Remote Similarity NPC309203

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC239608 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
0.5556 Remote Similarity NPD824 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