Natural Product: NPC185497

Natural Product IDNPC185497
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 5,7-Dihydroxychromone
IUPAC Name 5,7-dihydroxychromen-4-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL3604316
PubChem CID 5281343
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0000144] Chromones

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 NYCXYKOXLNBYID-UHFFFAOYSA-N
Standard InCHI InChI=1S/C9H6O4/c10-5-3-7(12)9-6(11)1-2-13-8(9)4-5/h1-4,10,12H
SMILES Oc1cc(O)c2c(c1)occc2=O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   178.03 Volume:   169.086
?
Van der Waals volume.
Dense:   1.053 LogP:   1.129
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.513
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.353
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   12.0
TPSA:   70.67
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.635 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.484 Fsp3:   0.0
MCE-18:   11.0
?
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:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.248 Fluc inhibitor:   0.04
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.3
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.098
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.955 Promiscuous compounds:   0.935

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.858 MDCK Permeability:   -4.847
Pgp-inhibitor:   0.055 Pgp-substrate:   0.504
PAMPA:   0.385
?
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):   0.031
20% Bioavailability (F20%):   0.412 30% Bioavailability (F30%):   0.786
50% Bioavailability (F50%):   0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.122 MRP1:   0.596
Plasma Protein Binding (PPB):   88.41% Volume Distribution (VD):   -0.336
Fu: 9.803%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.607
OATP1B3 inhibitor:   0.801 BCRP inhibitor:   0.901
BSEP inhibitor:   0.325

ADMET: Metabolism

CYP1A2-inhibitor:   0.794 CYP1A2-substrate:   0.116
CYP2C19-inhibitor:   0.012 CYP2C19-substrate:   0.123
CYP2C9-inhibitor:   0.888 CYP2C9-substrate:   0.793
CYP2D6-inhibitor:   0.91 CYP2D6-substrate:   0.892
CYP3A4-inhibitor:   0.002 CYP3A4-substrate:   0.08
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.886
HLM stability:   0.779
?
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):  6.267 Half-life (T1/2):  1.099

ADMET: Toxicity

hERG Blockers:  0.096 hERG Blockers (10um):  0.463
Human Hepatotoxicity (H-HT):  0.462 Drug-induced Liver Injury (DILI):  0.696
AMES Toxicity:  0.706 Rat Oral Acute Toxicity:  0.639
Maximum Recommended Daily Dose:  0.819 Skin Sensitization:  0.308
Carcinogencity:  0.751 Eye Corrosion:  0.233
Eye Irritation:  0.995 Respiratory Toxicity:  0.885
Drug-induced Neurotoxicity:  0.181 Ototoxicity:  0.145
Hematotoxicity:  0.145 Drug-induced Nephrotoxicity:  0.147
Genotoxicity:  0.963 RPMI-8226 Immunitoxicity:  0.089
A549 Cytotoxicity:  0.248 Hek293 Cytotoxicity:  0.554
BCF:   0.926
?
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:   3.288
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.17
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.581
?
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
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. 2007; 2008 DOI[10.1007/s11746-010-1589-7]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1080/10496475.2013.791908]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. aerial part n.a. PMID[11141127]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. cotyledon n.a. PMID[11283027]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[12670184]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. rhizome n.a. PMID[14993759]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[15595606]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[15787460]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[15787460]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[16203143]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[16394559]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562827]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[16919944]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. root n.a. PMID[17480099]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota roots Phitsanulok Province, Thailand 2004-MAY PMID[17480099]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota root bark n.a. n.a. PMID[17608532]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[17950599]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota fruits n.a. n.a. PMID[19113968]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota Roots n.a. n.a. PMID[19191562]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[19280148]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[19285413]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[19660948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[21348467]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. PMID[22537213]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24456525]
NPO5645 Silybum marianum Species Asteraceae Eukaryota Seeds n.a. n.a. PMID[24597776]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota Root barks n.a. n.a. PMID[25051453]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota Roots n.a. n.a. PMID[25322455]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO5755.1 Bauhinia glauca Under-species n.a. n.a. n.a. n.a. n.a. PMID[26096681]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota root barks purchased from the local herbal market, Chungbuk, Korea 2012-JUL PMID[26227773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[27420919]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO25426 Arachis hypogaea Species n.a. n.a. Peanut Skins n.a. n.a. PMID[28231711]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[35268681]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. PMID[36431807]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38308284]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[39410132]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. whole plant n.a. PMID[8588862]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3357 Alnus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4628 Aloe deltoideodonta Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4382 Elmerrillia papuana n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO1490 Goldfussia yunnanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO8807 Laurentia longiflora n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9608 Lepraria citrina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8977 Notholaena aschenborniana Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9881 Petrosia hebes Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6828 Purpura aperta Species Muricidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25475 Syphonota geographica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2455 Thermopsis mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Oil n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. Oils n.a. Database[Phenol-Explorer]
NPO25426 Arachis hypogaea Species n.a. n.a. Seeds n.a. Database[Phenol-Explorer]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1490 Goldfussia yunnanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9881 Petrosia hebes Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4628 Aloe deltoideodonta Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8977 Notholaena aschenborniana Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3357 Alnus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2455 Thermopsis mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6828 Purpura aperta Species Muricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9608 Lepraria citrina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8807 Laurentia longiflora n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4382 Elmerrillia papuana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25475 Syphonota geographica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25426 Arachis hypogaea Species n.a. n.a. 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
NPT1120 Individual protein Pancreatic triacylglycerol lipase Sus scrofa Inhibition = 17.5 % PMID[26227773]
NPT1120 Individual protein Pancreatic triacylglycerol lipase Sus scrofa IC50 > 100000.0 nM PMID[26227773]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 6.83 % PMID[26096681]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. EC50 = 1900.0 nM PMID[27420919]

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 NPC185497 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
0.6098 Remote Similarity NPC65060
0.5714 Remote Similarity NPC60558
0.5556 Remote Similarity NPC143903
0.5532 Remote Similarity NPC193792
0.5455 Remote Similarity NPC270369
0.5217 Remote Similarity NPC296380
0.5102 Remote Similarity NPC39426
0.5102 Remote Similarity NPC608554

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC185497 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
0.5102 Remote Similarity NPD1510 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