Natural Product: NPC314329

Natural Product IDNPC314329
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Flavanone
IUPAC Name 2-phenyl-2,3-dihydrochromen-4-one
Synonyms NSC-50393
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL274318
PubChem CID 10251
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0001632] Flavanones

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 ZONYXWQDUYMKFB-UHFFFAOYSA-N
Standard InCHI InChI=1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
SMILES O=C1CC(Oc2c1cccc2)c1ccccc1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   224.08 Volume:   241.452
?
Van der Waals volume.
Dense:   0.928 LogP:   3.188
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.265
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.621
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   18.0
TPSA:   26.3
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.742 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.261 Fsp3:   0.133
MCE-18:   45.294
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.511 Fluc inhibitor:   0.63
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.23
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.256
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.795 Promiscuous compounds:   0.102

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.496 MDCK Permeability:   -4.576
Pgp-inhibitor:   1.0 Pgp-substrate:   0.01
PAMPA:   0.097
?
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%):   0.0 30% Bioavailability (F30%):   0.123
50% Bioavailability (F50%):   0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.976 MRP1:   0.771
Plasma Protein Binding (PPB):   96.908% Volume Distribution (VD):   -0.002
Fu: 2.582%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.849
OATP1B3 inhibitor:   0.996 BCRP inhibitor:   0.813
BSEP inhibitor:   0.997

ADMET: Metabolism

CYP1A2-inhibitor:   0.765 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.612 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   0.43 CYP2C9-substrate:   0.001
CYP2D6-inhibitor:   0.07 CYP2D6-substrate:   0.944
CYP3A4-inhibitor:   0.298 CYP3A4-substrate:   0.008
CYP2B6-substrate:   0.107 CYP2C8-inhibitor:   0.529
HLM stability:   0.999
?
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):  4.088 Half-life (T1/2):  1.843

ADMET: Toxicity

hERG Blockers:  0.311 hERG Blockers (10um):  0.654
Human Hepatotoxicity (H-HT):  0.778 Drug-induced Liver Injury (DILI):  0.534
AMES Toxicity:  0.601 Rat Oral Acute Toxicity:  0.466
Maximum Recommended Daily Dose:  0.43 Skin Sensitization:  0.56
Carcinogencity:  0.653 Eye Corrosion:  0.074
Eye Irritation:  0.967 Respiratory Toxicity:  0.414
Drug-induced Neurotoxicity:  0.807 Ototoxicity:  0.295
Hematotoxicity:  0.367 Drug-induced Nephrotoxicity:  0.671
Genotoxicity:  0.189 RPMI-8226 Immunitoxicity:  0.041
A549 Cytotoxicity:  0.137 Hek293 Cytotoxicity:  0.348
BCF:   1.459
?
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:   4.032
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.941
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.65
?
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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11240-015-0761-z]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s12010-013-0354-4]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1055/S-2006-958077]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1186/s40064-015-0831-z]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1501/Tarimbil_0000001065]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11473446]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. fruit n.a. PMID[16417304]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[21608987]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. PMID[36557810]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[37446586]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[37570937]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO65033 Eurypon laughlini Species Suberitidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Bulb n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit Juice n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruits n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO65033 Eurypon laughlini Species Suberitidae Eukaryota n.a. n.a. n.a. DOI[http://dx.doi.org/10.3906/bot-1801-22]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae 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
NPO10856 Passiflora edulis Other Fruit 1030 1000 1060 mg/100g Database [DUKE]
NPO17024 Vitis vinifera Raw Leaf 4500 4000 5000 mg/100g Database [DUKE]
NPO1751 Ribes nigrum Other Leaf 460 460 460 mg/100g Database [DUKE]
NPO22234 Ficus carica Other (raw) Leaf 530 530 530 mg/100g Database [DUKE]
NPO24124 Curcuma longa Other Rhizome 9.25 9 9.5 mg/100g Database [DUKE]

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
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 32000.0 nM PMID[8691424]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Ki = 50100.0 nM PMID[8691424]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens pKi(uM) = -1.21 n.a. PMID[9438021]
NPT299 Individual protein Androgen Receptor Rattus norvegicus IC50 = 54954.09 nM PMID[16134935]
NPT1587 Individual protein Estradiol 17-beta-dehydrogenase 1 Homo sapiens Activity = 110.0 % PMID[18533708]
NPT1588 Individual protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens Activity = 70.7 % PMID[18533708]
NPT153 Individual protein Androgen Receptor Homo sapiens IC50 = 20000.0 nM PMID[19592245]
NPT249 Individual protein Glucocorticoid receptor Homo sapiens EC150 = 380.0 uM PMID[19592245]
NPT153 Individual protein Androgen Receptor Homo sapiens EC150 = 380.0 uM PMID[19592245]
NPT149 Individual protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 39810.7 nM PubChem BioAssay data set
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 79432.8 nM PubChem BioAssay data set
NPT1474 Individual protein ATP-dependent Clp protease proteolytic subunit Bacillus subtilis (strain 168) Potency n.a. 15848.9 nM PubChem BioAssay data set
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT160 Individual protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT161 Individual protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 56234.1 nM PubChem BioAssay data set
NPT582 Individual protein Monoamine oxidase B Homo sapiens IC50 = 2870.0 nM PMID[20045650]
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 79.68 % PMID[23571415]
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 76.99 % PMID[23571415]
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens IC50 = 28500.0 nM PMID[11909717]
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens IC50 = 28000.0 nM PMID[18042388]
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens Activity = 0.2 n.a. PMID[18042388]
NPT442 Individual protein Ferritin light chain Equus caballus Potency = 25118.9 nM PubChem BioAssay data set
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens IC50 = 8000.0 nM PMID[26301554]
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens IC50 = 13803.84 nM PMID[28622580]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT181 Cell line Bel-7402 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[17137679]
NPT83 Cell line MCF7 Homo sapiens IC50 > 25.0 ug.mL-1 PMID[17137679]
NPT306 Cell line PC-3 Homo sapiens IC50 = 16.6 ug.mL-1 PMID[17137679]
NPT116 Cell line HL-60 Homo sapiens IC50 = 3.4 ug.mL-1 PMID[17137679]
NPT81 Cell line A549 Homo sapiens IC50 = 14.2 ug.mL-1 PMID[17137679]
NPT384 Cell line TK-10 Homo sapiens Activity = 79.0 % PMID[17383189]
NPT83 Cell line MCF7 Homo sapiens Activity = 54.0 % PMID[17383189]
NPT139 Cell line HT-29 Homo sapiens Activity = 69.0 % PMID[17383189]
NPT759 Cell line H9 Homo sapiens IC50 = 45000.0 nM PMID[8158164]
NPT71 Cell line HEK293 Homo sapiens FC = 2.3 n.a. PMID[19307119]
NPT520 Cell line 3T3-L1 Mus musculus Activity = 5.1 % PMID[21493073]
NPT520 Cell line 3T3-L1 Mus musculus Activity = -1.9 % PMID[21493073]
NPT520 Cell line 3T3-L1 Mus musculus Activity = 2.5 % PMID[21493073]
NPT520 Cell line 3T3-L1 Mus musculus Activity = 1.0 % PMID[21493073]
NPT369 Cell line ACHN Homo sapiens GI50 n.a. 47643.1 nM PubChem BioAssay data set
NPT370 Cell line NCI-H23 Homo sapiens GI50 n.a. 15885.47 nM PubChem BioAssay data set
NPT371 Cell line UO-31 Homo sapiens GI50 n.a. 47643.1 nM PubChem BioAssay data set
NPT372 Cell line HOP-92 Homo sapiens GI50 n.a. 24945.95 nM PubChem BioAssay data set
NPT116 Cell line HL-60 Homo sapiens GI50 n.a. 21478.3 nM PubChem BioAssay data set
NPT90 Cell line DU-145 Homo sapiens GI50 n.a. 67608.3 nM PubChem BioAssay data set
NPT374 Cell line SF-539 Homo sapiens GI50 n.a. 21777.1 nM PubChem BioAssay data set
NPT373 Cell line SK-MEL-5 Homo sapiens GI50 n.a. 25061.09 nM PubChem BioAssay data set
NPT111 Cell line K562 Homo sapiens GI50 n.a. 12589.25 nM PubChem BioAssay data set
NPT376 Cell line A498 Homo sapiens GI50 n.a. 30338.91 nM PubChem BioAssay data set
NPT112 Cell line MOLT-4 Homo sapiens GI50 n.a. 13740.42 nM PubChem BioAssay data set
NPT379 Cell line HOP-62 Homo sapiens GI50 n.a. 48417.24 nM PubChem BioAssay data set
NPT378 Cell line NCI/ADR-RES Homo sapiens GI50 n.a. 34914.03 nM PubChem BioAssay data set
NPT380 Cell line U-251 Homo sapiens GI50 n.a. 38636.7 nM PubChem BioAssay data set
NPT381 Cell line OVCAR-8 Homo sapiens GI50 n.a. 48865.24 nM PubChem BioAssay data set
NPT82 Cell line MDA-MB-231 Homo sapiens GI50 n.a. 32210.69 nM PubChem BioAssay data set
NPT383 Cell line SNB-19 Homo sapiens GI50 n.a. 23067.47 nM PubChem BioAssay data set
NPT385 Cell line SR Homo sapiens GI50 n.a. 24043.63 nM PubChem BioAssay data set
NPT384 Cell line TK-10 Homo sapiens GI50 n.a. 76383.58 nM PubChem BioAssay data set
NPT323 Cell line SW-620 Homo sapiens GI50 n.a. 10000.0 nM PubChem BioAssay data set
NPT386 Cell line KM12 Homo sapiens GI50 n.a. 35727.28 nM PubChem BioAssay data set
NPT387 Cell line M14 Homo sapiens GI50 n.a. 51880.0 nM PubChem BioAssay data set
NPT388 Cell line NCI-H322M Homo sapiens GI50 n.a. 93325.43 nM PubChem BioAssay data set
NPT389 Cell line RPMI-8226 Homo sapiens GI50 n.a. 17139.57 nM PubChem BioAssay data set
NPT456 Cell line OVCAR-4 Homo sapiens GI50 n.a. 66069.34 nM PubChem BioAssay data set
NPT390 Cell line LOX IMVI Homo sapiens GI50 n.a. 26546.06 nM PubChem BioAssay data set
NPT457 Cell line BT-549 Homo sapiens GI50 n.a. 15381.55 nM PubChem BioAssay data set
NPT147 Cell line SK-MEL-2 Homo sapiens GI50 n.a. 30060.76 nM PubChem BioAssay data set
NPT391 Cell line HCC 2998 Homo sapiens GI50 n.a. 76913.04 nM PubChem BioAssay data set
NPT392 Cell line SNB-75 Homo sapiens GI50 n.a. 63386.97 nM PubChem BioAssay data set
NPT148 Cell line HCT-15 Homo sapiens GI50 n.a. 26061.54 nM PubChem BioAssay data set
NPT393 Cell line HCT-116 Homo sapiens GI50 n.a. 30269.13 nM PubChem BioAssay data set
NPT395 Cell line SF-268 Homo sapiens GI50 n.a. 64714.26 nM PubChem BioAssay data set
NPT394 Cell line EKVX Homo sapiens GI50 n.a. 38904.51 nM PubChem BioAssay data set
NPT306 Cell line PC-3 Homo sapiens GI50 n.a. 38459.18 nM PubChem BioAssay data set
NPT83 Cell line MCF7 Homo sapiens GI50 n.a. 37757.22 nM PubChem BioAssay data set
NPT146 Cell line SK-OV-3 Homo sapiens GI50 n.a. 84139.51 nM PubChem BioAssay data set
NPT396 Cell line T47D Homo sapiens GI50 n.a. 35809.64 nM PubChem BioAssay data set
NPT397 Cell line NCI-H460 Homo sapiens GI50 n.a. 32136.61 nM PubChem BioAssay data set
NPT308 Cell line CAKI-1 Homo sapiens GI50 n.a. 48305.88 nM PubChem BioAssay data set
NPT398 Cell line UACC-62 Homo sapiens GI50 n.a. 51286.14 nM PubChem BioAssay data set
NPT400 Cell line MDA-MB-435 Homo sapiens GI50 n.a. 31915.38 nM PubChem BioAssay data set
NPT399 Cell line SF-295 Homo sapiens GI50 n.a. 58076.44 nM PubChem BioAssay data set
NPT458 Cell line IGROV-1 Homo sapiens GI50 n.a. 23442.29 nM PubChem BioAssay data set
NPT402 Cell line Hs-578T Homo sapiens GI50 n.a. 67297.67 nM PubChem BioAssay data set
NPT401 Cell line 786-0 Homo sapiens GI50 n.a. 29308.93 nM PubChem BioAssay data set
NPT403 Cell line UACC-257 Homo sapiens GI50 n.a. 77268.06 nM PubChem BioAssay data set
NPT404 Cell line CCRF-CEM Homo sapiens GI50 n.a. 24210.29 nM PubChem BioAssay data set
NPT405 Cell line NCI-H226 Homo sapiens GI50 n.a. 32359.37 nM PubChem BioAssay data set
NPT139 Cell line HT-29 Homo sapiens GI50 n.a. 27989.81 nM PubChem BioAssay data set
NPT170 Cell line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT406 Cell line RXF 393 Homo sapiens GI50 n.a. 36224.3 nM PubChem BioAssay data set
NPT407 Cell line COLO 205 Homo sapiens GI50 n.a. 33573.76 nM PubChem BioAssay data set
NPT1653 Cell line WM-115 Homo sapiens IC50 = 71200.0 nM PMID[23756061]
NPT623 Cell line NALM-6 Homo sapiens IC50 = 57600.0 nM PMID[23756061]
NPT116 Cell line HL-60 Homo sapiens IC50 = 51100.0 nM PMID[23756061]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 27.7 ug.mL-1 PMID[17137679]
NPT20 Organism Candida albicans Candida albicans IC50 > 50.0 ug.mL-1 PMID[12502337]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda log10LT50 = 1.656 n.a. PMID[20415424]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 71200.0 nM PMID[25091929]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 57600.0 nM PMID[25091929]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 51100.0 nM PMID[27234147]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 > 50.0 ug.mL-1 PMID[12502337]
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus EC50 = 0.09 g/m2 PMID[12762809]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 58000.0 nM PMID[8158164]
NPT1 Others Radical scavenging activity n.a. Inhibition = 2.6 % DOI[10.1007/s00044-007-9060-5]
NPT2555 Others Adenosine receptors; A1 & A3 Rattus norvegicus Ratio = 0.64 n.a. PMID[8691424]
NPT2 Others Unspecified n.a. Activity = 6.5 % PMID[2959755]
NPT2 Others Unspecified n.a. Activity = 84.8 % PMID[2959755]
NPT2 Others Unspecified n.a. Activity = 73.4 % PMID[2959755]
NPT2 Others Unspecified n.a. IC50 = 310.0 nM PMID[2959755]
NPT2 Others Unspecified n.a. IC50 > 50.0 ug.mL-1 PMID[12502337]
NPT2 Others Unspecified n.a. Activity = 2.82 /M PMID[19236029]
NPT2 Others Unspecified n.a. Ratio IC50 > 35.0 n.a. PMID[20045650]
NPT2 Others Unspecified n.a. Potency n.a. 5623.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. ID50 > 445.9 uM PMID[1378087]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus Protection = 24.0 % DOI[10.1016/0960-894X(96)00134-5]





 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 NPC314329 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 NPC603208
0.6905 Remote Similarity NPC485642
0.6905 Remote Similarity NPC611561
0.675 Remote Similarity NPC228184
0.6591 Remote Similarity NPC476480
0.6591 Remote Similarity NPC84585
0.5833 Remote Similarity NPC99597
0.5652 Remote Similarity NPC265871
0.5652 Remote Similarity NPC205093
0.5476 Remote Similarity NPC486692
0.5435 Remote Similarity NPC329225
0.5435 Remote Similarity NPC147686
0.5417 Remote Similarity NPC243083
0.5417 Remote Similarity NPC13768
0.5417 Remote Similarity NPC287246
0.5417 Remote Similarity NPC204515
0.5306 Remote Similarity NPC150648
0.5306 Remote Similarity NPC312391
0.5208 Remote Similarity NPC22467
0.52 Remote Similarity NPC255106
0.52 Remote Similarity NPC482119
0.52 Remote Similarity NPC235165
0.52 Remote Similarity NPC482120
0.5094 Remote Similarity NPC472409

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC314329 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
1.0 High Similarity NPD1547 Clinical (unspecified phase)
0.5435 Remote Similarity NPD1549 Phase 2
0.5417 Remote Similarity NPD1550 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