Natural Product: NPC30432

Natural Product IDNPC30432
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Physcion 8-O-Glucoside
IUPAC Name 1-hydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Synonyms Physcion 8-O-Glucoside
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL457944
PubChem CID 5319323
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

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 WLXGUTUUWXVZNM-DQMLXFRHSA-N
Standard InCHI InChI=1S/C22H22O10/c1-8-3-10-16(19(27)15-11(17(10)25)5-9(30-2)6-12(15)24)13(4-8)31-22-21(29)20(28)18(26)14(7-23)32-22/h3-6,14,18,20-24,26,28-29H,7H2,1-2H3/t14-,18-,20+,21-,22-/m1/s1
SMILES OC[C@H]1O[C@@H](Oc2cc(C)cc3c2C(=O)c2c(C3=O)cc(cc2O)OC)[C@@H]([C@H]([C@@H]1O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   446.12 Volume:   421.653
?
Van der Waals volume.
Dense:   1.058 LogP:   1.999
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.284
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.811
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   24.0
TPSA:   162.98
?
Topological Polar Surface Area.
 H-Bond Acceptor:   10.0
H-Bond Donor:   5.0 Rings:   4.0
Heavy Atoms:   10.0

MedChem Properties

QED Drug-Likeness Score:   0.358 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.855 Fsp3:   0.364
MCE-18:   90.0
?
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:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   1
Colloidal aggregators:   0.508 Fluc inhibitor:   0.142
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.365
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.761
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.152 Promiscuous compounds:   0.363

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.857 MDCK Permeability:   -5.067
Pgp-inhibitor:   0.03 Pgp-substrate:   0.087
PAMPA:   0.978
?
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):   0.749
20% Bioavailability (F20%):   0.023 30% Bioavailability (F30%):   0.952
50% Bioavailability (F50%):   0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.426
Plasma Protein Binding (PPB):   92.884% Volume Distribution (VD):   0.321
Fu: 5.915%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.03
BSEP inhibitor:   0.026

ADMET: Metabolism

CYP1A2-inhibitor:   0.149 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.026
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.001
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.002
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.003
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.997
HLM stability:   0.062
?
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):  2.951 Half-life (T1/2):  2.926

ADMET: Toxicity

hERG Blockers:  0.038 hERG Blockers (10um):  0.167
Human Hepatotoxicity (H-HT):  0.884 Drug-induced Liver Injury (DILI):  0.994
AMES Toxicity:  0.98 Rat Oral Acute Toxicity:  0.063
Maximum Recommended Daily Dose:  0.056 Skin Sensitization:  0.996
Carcinogencity:  0.67 Eye Corrosion:  0.0
Eye Irritation:  0.337 Respiratory Toxicity:  0.066
Drug-induced Neurotoxicity:  0.049 Ototoxicity:  0.955
Hematotoxicity:  0.879 Drug-induced Nephrotoxicity:  0.888
Genotoxicity:  0.879 RPMI-8226 Immunitoxicity:  0.291
A549 Cytotoxicity:  0.854 Hek293 Cytotoxicity:  0.423
BCF:   0.895
?
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:   3.585
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.997
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.281
?
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
NPO12079 Dysoxylum cumingianum Species Meliaceae Eukaryota n.a. leaf n.a. DOI[10.1021/jo00051a050]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO14520 Bassia muricata Species Chenopodiaceae Eukaryota n.a. aerial part n.a. PMID[11454355]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota Roots Gorkha district, Nepal 1996-OCT PMID[12932135]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. root n.a. PMID[16564530]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[19719093]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[22512738]
NPO13237 Teucrium yemense Species n.a. n.a. Aerial Parts n.a. n.a. PMID[28581290]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[29359942]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[31944695]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots; Tubers n.a. n.a. PMID[7714535]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7819.1 Epichloe festucae var. lolii Varieties Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15297 Aconitum seravschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13716 Aconitum tasiromontanum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14217 Adansonia grandidieri Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14412 Aphyllocladus denticulatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2631 Aster sedifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14520 Bassia muricata Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4345 Caulocystis cephalornithos Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16590 Cytophaga hutchinsoni Species Cytophagaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO14104 Dendriopoterium menendezii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9448 Dictyopteris australis Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12079 Dysoxylum cumingianum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8386 Enceliopsis argophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11749 Eria mollis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10688 Flacourtia jangomas Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13403 Gadus morhua callarias Species Gadidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO624 Isaria fumosorosea Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22526 Justicia secunda Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3214 Lavandula vera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9752 Miliusa velutina Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13523 Neobalanocarpus heimii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12252 Psychotria stachyoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO986 Rattus rattus Species Muridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2198 Rivularia firma Species Rivulariaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO1501 Senecio subdentatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13421 Sphaerella laricina n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO13237 Teucrium yemense Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15297 Aconitum seravschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16590 Cytophaga hutchinsoni Species Cytophagaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2631 Aster sedifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12252 Psychotria stachyoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO624 Isaria fumosorosea Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14412 Aphyllocladus denticulatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8386 Enceliopsis argophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9448 Dictyopteris australis Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13237 Teucrium yemense Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14520 Bassia muricata Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4345 Caulocystis cephalornithos Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2198 Rivularia firma Species Rivulariaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13523 Neobalanocarpus heimii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3214 Lavandula vera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14217 Adansonia grandidieri Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7819.1 Epichloe festucae var. lolii Varieties Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12079 Dysoxylum cumingianum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10688 Flacourtia jangomas Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15297 Aconitum seravschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13716 Aconitum tasiromontanum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1501 Senecio subdentatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22526 Justicia secunda Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14104 Dendriopoterium menendezii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13403 Gadus morhua callarias Species Gadidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13421 Sphaerella laricina n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9752 Miliusa velutina Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11749 Eria mollis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO986 Rattus rattus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae 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
NPT1 Others Radical scavenging activity n.a. IC50 > 100.0 ug.mL-1 PMID[12932135]

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 NPC30432 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
0.7576 Intermediate Similarity NPC5029
0.7576 Intermediate Similarity NPC146837
0.7353 Intermediate Similarity NPC76128
0.7231 Intermediate Similarity NPC111536
0.6812 Remote Similarity NPC271385
0.6615 Remote Similarity NPC222455
0.6571 Remote Similarity NPC278329
0.6389 Remote Similarity NPC212099
0.6377 Remote Similarity NPC604892
0.6271 Remote Similarity NPC118027
0.6269 Remote Similarity NPC483778
0.625 Remote Similarity NPC212290
0.6125 Remote Similarity NPC46958
0.6111 Remote Similarity NPC605700
0.6111 Remote Similarity NPC606849
0.5946 Remote Similarity NPC199357
0.5942 Remote Similarity NPC605264
0.5909 Remote Similarity NPC23084
0.5811 Remote Similarity NPC101116
0.5694 Remote Similarity NPC146803
0.5616 Remote Similarity NPC210192
0.56 Remote Similarity NPC604833
0.5556 Remote Similarity NPC610808
0.5541 Remote Similarity NPC99233
0.5526 Remote Similarity NPC606202
0.5455 Remote Similarity NPC214454
0.5385 Remote Similarity NPC12308
0.5312 Remote Similarity NPC152722
0.5294 Remote Similarity NPC218685
0.527 Remote Similarity NPC600107
0.5068 Remote Similarity NPC199335
0.5063 Remote Similarity NPC61594
0.5063 Remote Similarity NPC219163

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC30432 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