Natural Product: NPC115159

Natural Product IDNPC115159
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (Z)-1-(2,4-Dihydroxyphenyl)-3-(4-Hydroxyphenyl)Prop-2-En-1-One
IUPAC Name (Z)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1395334
PubChem CID 6603886
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003472] 2'-Hydroxychalcones

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 DXDRHHKMWQZJHT-BAQGIRSFSA-N
Standard InCHI InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3-
SMILES c1cc(ccc1/C=CC(=O)c1ccc(cc1O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   256.07 Volume:   264.953
?
Van der Waals volume.
Dense:   0.966 LogP:   2.788
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.752
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.572
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   14.0
TPSA:   77.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   3.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.583 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.056 Fsp3:   0.0
MCE-18:   12.0
?
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:   0 PAINS Alert:   0
Colloidal aggregators:   0.923 Fluc inhibitor:   1.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.485
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.387
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.988 Promiscuous compounds:   0.439

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.893 MDCK Permeability:   -4.795
Pgp-inhibitor:   0.198 Pgp-substrate:   0.009
PAMPA:   0.263
?
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):   0.004
20% Bioavailability (F20%):   0.468 30% Bioavailability (F30%):   0.791
50% Bioavailability (F50%):   0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.007 MRP1:   0.178
Plasma Protein Binding (PPB):   96.038% Volume Distribution (VD):   -0.298
Fu: 5.283%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.981
OATP1B3 inhibitor:   0.997 BCRP inhibitor:   0.623
BSEP inhibitor:   0.698

ADMET: Metabolism

CYP1A2-inhibitor:   0.63 CYP1A2-substrate:   0.962
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.917
CYP2C9-inhibitor:   0.957 CYP2C9-substrate:   0.997
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   0.998
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.998
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.354
?
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):  6.376 Half-life (T1/2):  1.482

ADMET: Toxicity

hERG Blockers:  0.316 hERG Blockers (10um):  0.593
Human Hepatotoxicity (H-HT):  0.514 Drug-induced Liver Injury (DILI):  0.011
AMES Toxicity:  0.406 Rat Oral Acute Toxicity:  0.08
Maximum Recommended Daily Dose:  0.386 Skin Sensitization:  0.998
Carcinogencity:  0.043 Eye Corrosion:  0.512
Eye Irritation:  0.999 Respiratory Toxicity:  0.592
Drug-induced Neurotoxicity:  0.469 Ototoxicity:  0.14
Hematotoxicity:  0.008 Drug-induced Nephrotoxicity:  0.237
Genotoxicity:  0.156 RPMI-8226 Immunitoxicity:  0.052
A549 Cytotoxicity:  0.607 Hek293 Cytotoxicity:  0.722
BCF:   1.35
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.158
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.635
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.382
?
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
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11164-015-2099-x]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s40502-015-0143-x]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1093/pcp/pcg054]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1134/S1021443709050069]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1134/S1021443711030101]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota bark n.a. n.a. PMID[12828464]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. stem n.a. PMID[14510590]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota Roots n.a. n.a. PMID[2045815]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. root n.a. PMID[2045815]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[39683057]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22420 Lignum dalbergiae odoriferae rosewood n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8300 Apis mellifera ligustica Species Apidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO277 Caulis millettiae n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15124 Herba sedi sarmentosi n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO3982 Dalbergia stevensonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3982 Dalbergia stevensonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15124 Herba sedi sarmentosi n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO8300 Apis mellifera ligustica Species Apidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO277 Caulis millettiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO22420 Lignum dalbergiae odoriferae rosewood n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15711 Radix glycyrrhizae preparata Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28394 Rohdea chinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3982 Dalbergia stevensonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10331 Allium ascalonicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28394 Rohdea chinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17207 Panicum miliaceum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3982 Dalbergia stevensonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17729 Tephrosia toxicaria Species Geometridae 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 Potency = 3162.3 nM PubChem BioAssay data set
NPT2741 Individual protein Pyruvate kinase Leishmania mexicana Potency = 12589.3 nM PubChem BioAssay data set
NPT213 Individual protein Cytochrome P450 2C19 Homo sapiens Potency = 12589.3 nM PubChem BioAssay data set
NPT282 Individual protein MAP kinase ERK2 Homo sapiens Potency = 251.2 nM PubChem BioAssay data set
NPT149 Individual protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 10000.0 nM PubChem BioAssay data set
NPT109 Individual protein Cytochrome P450 3A4 Homo sapiens Potency = 3162.3 nM PubChem BioAssay data set
NPT110 Individual protein Cytochrome P450 2D6 Homo sapiens Potency = 15848.9 nM PubChem BioAssay data set
NPT212 Individual protein Cytochrome P450 2C9 Homo sapiens Potency = 19952.6 nM PubChem BioAssay data set
NPT212 Individual protein Cytochrome P450 2C9 Homo sapiens AC50 = 19952.62 nM PubChem BioAssay data set
NPT213 Individual protein Cytochrome P450 2C19 Homo sapiens AC50 = 12589.25 nM PubChem BioAssay data set
NPT109 Individual protein Cytochrome P450 3A4 Homo sapiens AC50 = 3162.28 nM PubChem BioAssay data set
NPT208 Individual protein Cytochrome P450 1A2 Homo sapiens AC50 = 5011.87 nM PubChem BioAssay data set
NPT110 Individual protein Cytochrome P450 2D6 Homo sapiens AC50 = 15848.93 nM PubChem BioAssay data set
NPT484 Individual protein Luciferin 4-monooxygenase Photinus pyralis Potency = 25118.9 nM PubChem BioAssay data set
NPT96 Individual protein Thrombopoietin Homo sapiens Potency = 3162.3 nM PubChem BioAssay data set
NPT792 Individual protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set
NPT52 Individual protein Pyruvate kinase isozymes M1/M2 Homo sapiens Potency = 15848.9 nM PubChem BioAssay data set
NPT539 Individual protein Cellular tumor antigen p53 Homo sapiens Potency = 31622.8 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified n.a. Potency n.a. 10000.0 nM PubChem BioAssay data set

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 NPC115159 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 NPC19174
0.8378 Intermediate Similarity NPC297186
0.8158 Intermediate Similarity NPC26697
0.7778 Intermediate Similarity NPC267552
0.7561 Intermediate Similarity NPC262359
0.75 Intermediate Similarity NPC13238
0.7368 Intermediate Similarity NPC73532
0.7333 Intermediate Similarity NPC44960
0.7 Intermediate Similarity NPC224273
0.7 Intermediate Similarity NPC122793
0.6957 Remote Similarity NPC169250
0.6889 Remote Similarity NPC190043
0.6889 Remote Similarity NPC254659
0.6829 Remote Similarity NPC167205
0.6757 Remote Similarity NPC17525
0.6744 Remote Similarity NPC205468
0.6667 Remote Similarity NPC144281
0.66 Remote Similarity NPC185526
0.65 Remote Similarity NPC158222
0.6327 Remote Similarity NPC65005
0.6226 Remote Similarity NPC190487
0.62 Remote Similarity NPC131039
0.617 Remote Similarity NPC72158
0.617 Remote Similarity NPC30501
0.6087 Remote Similarity NPC129132
0.5882 Remote Similarity NPC485637
0.58 Remote Similarity NPC213485
0.58 Remote Similarity NPC188879
0.5714 Remote Similarity NPC45438
0.5686 Remote Similarity NPC479645
0.5686 Remote Similarity NPC479648
0.566 Remote Similarity NPC235239
0.56 Remote Similarity NPC162612
0.5556 Remote Similarity NPC161617
0.5556 Remote Similarity NPC192304
0.5556 Remote Similarity NPC600232
0.5536 Remote Similarity NPC484050
0.5439 Remote Similarity NPC608873
0.5439 Remote Similarity NPC609853
0.5435 Remote Similarity NPC257756
0.5435 Remote Similarity NPC336114
0.5417 Remote Similarity NPC119660
0.5417 Remote Similarity NPC263670
0.54 Remote Similarity NPC98254
0.5385 Remote Similarity NPC269694
0.537 Remote Similarity NPC154304
0.5366 Remote Similarity NPC603691
0.5333 Remote Similarity NPC34070
0.5333 Remote Similarity NPC139813
0.5283 Remote Similarity NPC147688
0.5273 Remote Similarity NPC266689
0.5263 Remote Similarity NPC286006
0.5254 Remote Similarity NPC259767
0.5254 Remote Similarity NPC609169
0.5208 Remote Similarity NPC312318
0.5208 Remote Similarity NPC284556
0.5208 Remote Similarity NPC477243
0.5208 Remote Similarity NPC605344
0.5179 Remote Similarity NPC474998
0.5161 Remote Similarity NPC600882
0.5128 Remote Similarity NPC181709
0.5106 Remote Similarity NPC64359
0.5098 Remote Similarity NPC103356
0.5094 Remote Similarity NPC168105
0.5094 Remote Similarity NPC156590
0.5091 Remote Similarity NPC11056
0.5091 Remote Similarity NPC473017
0.5088 Remote Similarity NPC484873

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC115159 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