Natural Product: NPC270456

Natural Product IDNPC270456
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (3R)-Mucronulatol
IUPAC Name (3R)-3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Synonyms (3R)-Mucronulatol
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1087024
PubChem CID 13873811
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002586] O-methylated isoflavonoids
          • [CHEMONTID:0002606] 4'-O-methylated isoflavonoids
            • [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

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 NUNFZNIXYWTZMW-NSHDSACASA-N
Standard InCHI InChI=1S/C17H18O5/c1-20-14-6-5-13(17(21-2)16(14)19)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3/t11-/m0/s1
SMILES COc1c(ccc(c1O)OC)[C@@H]1COc2c(C1)ccc(c2)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   302.12 Volume:   305.051
?
Van der Waals volume.
Dense:   0.99 LogP:   2.486
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.576
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.552
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   17.0
TPSA:   68.15
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.912 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.932 Fsp3:   0.294
MCE-18:   55.636
?
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:   0.391 Fluc inhibitor:   0.942
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.036
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.196
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.338 Promiscuous compounds:   0.251

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.027 MDCK Permeability:   -4.795
Pgp-inhibitor:   0.05 Pgp-substrate:   0.334
PAMPA:   0.039
?
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):   0.0
20% Bioavailability (F20%):   0.526 30% Bioavailability (F30%):   0.275
50% Bioavailability (F50%):   0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.452 MRP1:   0.912
Plasma Protein Binding (PPB):   94.289% Volume Distribution (VD):   -0.54
Fu: 6.204%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.987
OATP1B3 inhibitor:   0.966 BCRP inhibitor:   0.452
BSEP inhibitor:   0.774

ADMET: Metabolism

CYP1A2-inhibitor:   0.999 CYP1A2-substrate:   0.911
CYP2C19-inhibitor:   0.891 CYP2C19-substrate:   0.872
CYP2C9-inhibitor:   0.888 CYP2C9-substrate:   0.584
CYP2D6-inhibitor:   0.986 CYP2D6-substrate:   0.569
CYP3A4-inhibitor:   0.999 CYP3A4-substrate:   0.913
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.745
HLM stability:   0.747
?
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):  3.796 Half-life (T1/2):  2.244

ADMET: Toxicity

hERG Blockers:  0.223 hERG Blockers (10um):  0.615
Human Hepatotoxicity (H-HT):  0.715 Drug-induced Liver Injury (DILI):  0.734
AMES Toxicity:  0.441 Rat Oral Acute Toxicity:  0.534
Maximum Recommended Daily Dose:  0.736 Skin Sensitization:  0.74
Carcinogencity:  0.641 Eye Corrosion:  0.086
Eye Irritation:  0.975 Respiratory Toxicity:  0.919
Drug-induced Neurotoxicity:  0.709 Ototoxicity:  0.517
Hematotoxicity:  0.189 Drug-induced Nephrotoxicity:  0.418
Genotoxicity:  0.576 RPMI-8226 Immunitoxicity:  0.113
A549 Cytotoxicity:  0.572 Hek293 Cytotoxicity:  0.602
BCF:   0.93
?
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:   3.524
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.779
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.212
?
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
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. seed n.a. DOI[10.1007/s11418-005-0009-z]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. seed n.a. PMID[10661881]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[10691704]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16378371]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16643065]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. leaf n.a. PMID[17124632]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. fruit n.a. PMID[17124632]
NPO15741 Embelia ribes Species Primulaceae Eukaryota roots n.a. n.a. PMID[17125236]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[17125236]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[18257536]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19177635]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19433363]
NPO14114 Dalbergia parviflora Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[19928832]
NPO10682 Cystoseira mediterranea Species Sargassaceae Eukaryota n.a. n.a. n.a. PMID[2045820]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. Sunan County, Gansu Province, China 2006-JUN PMID[20684529]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[22032651]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[22032651]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota whole plant Guide County, Qinghai Province, China 2008-AUG PMID[22775441]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[30219526]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[32705864]
NPO6065 Brassica carinata Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[36599374]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4536 Remirea maritima Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6065 Brassica carinata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14114 Dalbergia parviflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10682 Cystoseira mediterranea Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15553 Barringtonia acutangula Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6807 Ranunculus asiaticus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5857 Achlya heterosexualis Species Saprolegniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3151 Solanum lanceolatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4901 Arnica mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16182 Desmodium canadense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7418 Eucalyptus resinifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1281 Schleichera trijuga Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16096 Astragalus adsurgens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8938 Halobacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO4123 Trididemnum cyanophorum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7032 Marasmiellus troyanus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO784 Sinapis alba Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5457 Dalbergia congestiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4123 Trididemnum cyanophorum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9594 Lysimachia fordiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6065 Brassica carinata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8938 Halobacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16182 Desmodium canadense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13474 Euphrasia genargentea Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO593 Wikstroemia viridiflora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3838 Chrysosporum ovalisporum Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6807 Ranunculus asiaticus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2670 Maytenus chuchuhuasha Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10682 Cystoseira mediterranea Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4901 Arnica mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2439 Diplopterygium glaucum Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3151 Solanum lanceolatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16096 Astragalus adsurgens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10038.1 Abies pinsapo var. marocana Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9867 Ixeris debilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15741 Embelia ribes Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1281 Schleichera trijuga Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10132 Schizophyllum lobatum Species Schizophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7418 Eucalyptus resinifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1293 Streptomyces matensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5857 Achlya heterosexualis Species Saprolegniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9091 Orthosiphon spicatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9737 Ampelocera edentula Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10947 Aspilia parvifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5086 Alternaria macrospora Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10447 Triclisia subcordata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7032 Marasmiellus troyanus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4536 Remirea maritima Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21472 Pterolobium hexapetalum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7887 Schultesia guianensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5457 Dalbergia congestiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9998 Abies excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13641 Napoleonaea vogelii Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13520 Craibiodendron yunnanense Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15553 Barringtonia acutangula Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15206 Mabea fistulifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12581 Corydalis densiflora Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14114 Dalbergia parviflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT396 Cell line T47D Homo sapiens Activity > 100.0 uM PMID[19928832]
NPT396 Cell line T47D Homo sapiens Activity = 6.3 uM PMID[19928832]
NPT83 Cell line MCF7 Homo sapiens Activity = 7.8 uM PMID[19928832]
NPT83 Cell line MCF7 Homo sapiens Activity = 0.9 uM PMID[19928832]
NPT396 Cell line T47D Homo sapiens Activity = 6.4 uM PMID[19928832]
NPT396 Cell line T47D Homo sapiens Activity = 0.4 uM PMID[19928832]
NPT83 Cell line MCF7 Homo sapiens Activity > 100.0 uM PMID[19928832]

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 NPC270456 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 NPC265433
1.0 High Similarity NPC162659
0.75 Intermediate Similarity NPC26879
0.6604 Remote Similarity NPC479545
0.6364 Remote Similarity NPC230479
0.6364 Remote Similarity NPC482710
0.6364 Remote Similarity NPC50315
0.6275 Remote Similarity NPC193364
0.625 Remote Similarity NPC129684
0.625 Remote Similarity NPC299520
0.5965 Remote Similarity NPC173660
0.5873 Remote Similarity NPC70682
0.5818 Remote Similarity NPC479543
0.5667 Remote Similarity NPC236306
0.5455 Remote Similarity NPC2613
0.5333 Remote Similarity NPC127218
0.5172 Remote Similarity NPC479544
0.5161 Remote Similarity NPC132222
0.5147 Remote Similarity NPC131866
0.5075 Remote Similarity NPC293203

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC270456 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
0.6275 Remote Similarity NPD1610 Phase 2

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