Natural Product: NPC242893

Natural Product IDNPC242893
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 3-(3,4-Dihydroxyphenyl)-7-Hydroxychromen-4-One
IUPAC Name 3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
Synonyms 3',4',7-Trihydroxyisoflavone; 7,3',4'-Trihydroxyisoflavone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL13486
PubChem CID 5284648
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002901] Isoflav-2-enes
          • [CHEMONTID:0000494] Isoflavones

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 DDKGKOOLFLYZDL-UHFFFAOYSA-N
Standard InCHI InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H
SMILES Oc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   270.05 Volume:   265.186
?
Van der Waals volume.
Dense:   1.018 LogP:   1.676
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.814
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.681
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   18.0
TPSA:   90.9
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   3.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.591 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.253 Fsp3:   0.0
MCE-18:   17.0
?
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:   1 PAINS Alert:   1
Colloidal aggregators:   0.696 Fluc inhibitor:   0.971
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.986
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.459
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.838 Promiscuous compounds:   0.803

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.984 MDCK Permeability:   -4.807
Pgp-inhibitor:   0.002 Pgp-substrate:   0.121
PAMPA:   0.469
?
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):   0.044
20% Bioavailability (F20%):   0.975 30% Bioavailability (F30%):   0.992
50% Bioavailability (F50%):   0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.008 MRP1:   0.365
Plasma Protein Binding (PPB):   86.595% Volume Distribution (VD):   -0.462
Fu: 13.285%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.781
OATP1B3 inhibitor:   0.932 BCRP inhibitor:   0.923
BSEP inhibitor:   0.165

ADMET: Metabolism

CYP1A2-inhibitor:   0.545 CYP1A2-substrate:   0.774
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.477
CYP2C9-inhibitor:   0.213 CYP2C9-substrate:   0.416
CYP2D6-inhibitor:   0.948 CYP2D6-substrate:   0.735
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.975
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.998
HLM stability:   0.211
?
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):  12.469 Half-life (T1/2):  1.571

ADMET: Toxicity

hERG Blockers:  0.156 hERG Blockers (10um):  0.666
Human Hepatotoxicity (H-HT):  0.436 Drug-induced Liver Injury (DILI):  0.627
AMES Toxicity:  0.604 Rat Oral Acute Toxicity:  0.546
Maximum Recommended Daily Dose:  0.807 Skin Sensitization:  0.863
Carcinogencity:  0.671 Eye Corrosion:  0.188
Eye Irritation:  0.993 Respiratory Toxicity:  0.628
Drug-induced Neurotoxicity:  0.104 Ototoxicity:  0.367
Hematotoxicity:  0.062 Drug-induced Nephrotoxicity:  0.051
Genotoxicity:  0.934 RPMI-8226 Immunitoxicity:  0.026
A549 Cytotoxicity:  0.564 Hek293 Cytotoxicity:  0.518
BCF:   1.214
?
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:   3.927
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.547
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.231
?
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
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(79)80020-5]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. Brazilian n.a. PMID[10328294]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[10423860]
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]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[11054840]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota twigs n.a. n.a. PMID[1453182]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[15165152]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota leaves n.a. n.a. PMID[15165152]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[15863936]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. PMID[15911254]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
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]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18348535]
NPO32821 korean fermented soypaste Species n.a. n.a. n.a. n.a. n.a. PMID[18722771]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[19407970]
NPO33272 aged korean fermented soybean paste n.a. n.a. n.a. n.a. n.a. n.a. PMID[20022495]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. bark n.a. PMID[21553897]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[21848266]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21848266]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[23743282]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
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]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[34142352]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. PMID[36670952]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9525107]
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]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19912 Vellozia nanuzae Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18117 Dalbergia odorifera Species Fabaceae 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]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens 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]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota 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]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20680 Erythrina melanacantha 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]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[Title]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae 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]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19912 Vellozia nanuzae Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8707.1 Pueraria montana var. lobata Varieties 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
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens Ki = 38.0 nM PMID[19090668]
NPT2739 Individual protein Tyrosinase Mus musculus IC50 = 5230.0 nM PMID[20022495]
NPT1721 Individual protein Death-associated protein kinase 1 Homo sapiens IC50 = 280000.0 nM PMID[26322379]
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens IC50 = 38.0 nM PMID[27156768]
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens Ki = 15000.0 nM PMID[27156768]
NPT178 Individual protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 28.0 % PMID[28522265]
NPT99 Individual protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 1.8 n.a. PMID[19807106]
NPT99 Individual protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 7.5 n.a. PMID[19807106]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -13.69 % DOI[10.6019/CHEMBL4495564]
NPT967 Individual protein Xanthine dehydrogenase Homo sapiens IC50 = 16800.0 nM PMID[18722771]
NPT967 Individual protein Xanthine dehydrogenase Homo sapiens IC50 > 1000000.0 nM PMID[18722771]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT189 Cell line Vero Chlorocebus aethiops IC50 = 135000.0 nM PMID[16441066]
NPT848 Cell line N9 Homo sapiens IC50 > 100000.0 nM PMID[28073678]
NPT83 Cell line MCF7 Homo sapiens GI = 0.0 % PMID[28522265]
NPT660 Cell line SW480 Homo sapiens GI = 43.0 % PMID[28522265]
NPT65 Cell line HepG2 Homo sapiens GI = 3.0 % PMID[28522265]
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 0.0 % PMID[28522265]
NPT34 Cell line BV-2 Mus musculus IC50 > 100000.0 nM PMID[28911817]
NPT451 Organism Helicobacter pylori Helicobacter pylori MIC > 20.0 ug.mL-1 PMID[10328294]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.19 % DOI[10.6019/CHEMBL4495565]
NPT28438 Unchecked Unchecked n.a. IC50 = 70000.0 nM PMID[33646787]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 10540.0 nM PMID[20022495]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 31970.0 nM PMID[21848266]
NPT1 Others Radical scavenging activity n.a. IC50 = 28.7 nM PMID[18722771]
NPT1 Others Radical scavenging activity n.a. ED50 = 30.0 uM PMID[20800321]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 7100.0 nM PMID[16441066]
NPT22410 Cell line Melan-a Mus musculus IC50 = 7830.0 nM PMID[20022495]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Activity = 63.5 % PMID[35489224]





 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 NPC242893 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
0.8222 Intermediate Similarity NPC234560
0.766 Intermediate Similarity NPC212767
0.7143 Intermediate Similarity NPC324929
0.7037 Intermediate Similarity NPC80710
0.6792 Remote Similarity NPC209560
0.6792 Remote Similarity NPC490700
0.6735 Remote Similarity NPC188074
0.6731 Remote Similarity NPC487215
0.6727 Remote Similarity NPC139364
0.6667 Remote Similarity NPC38065
0.6667 Remote Similarity NPC235428
0.6545 Remote Similarity NPC12377
0.6481 Remote Similarity NPC203747
0.6481 Remote Similarity NPC609386
0.6429 Remote Similarity NPC191741
0.6275 Remote Similarity NPC218490
0.623 Remote Similarity NPC611071
0.6207 Remote Similarity NPC35544
0.6167 Remote Similarity NPC215311
0.6167 Remote Similarity NPC607759
0.5965 Remote Similarity NPC262623
0.5962 Remote Similarity NPC125449
0.5873 Remote Similarity NPC610903
0.5862 Remote Similarity NPC12175
0.5862 Remote Similarity NPC40290
0.5862 Remote Similarity NPC195763
0.5763 Remote Similarity NPC200060
0.5763 Remote Similarity NPC55162
0.5763 Remote Similarity NPC291802
0.5672 Remote Similarity NPC605730
0.5614 Remote Similarity NPC245382
0.5606 Remote Similarity NPC104406
0.5606 Remote Similarity NPC285623
0.5606 Remote Similarity NPC108859
0.5593 Remote Similarity NPC156953
0.5538 Remote Similarity NPC149875
0.5484 Remote Similarity NPC161124
0.537 Remote Similarity NPC39426
0.5362 Remote Similarity NPC123653
0.5345 Remote Similarity NPC181124
0.5345 Remote Similarity NPC100971
0.5306 Remote Similarity NPC60558
0.5303 Remote Similarity NPC266572
0.5294 Remote Similarity NPC223701
0.5294 Remote Similarity NPC472583
0.5294 Remote Similarity NPC7989
0.5238 Remote Similarity NPC215375
0.5211 Remote Similarity NPC607477
0.5091 Remote Similarity NPC70136
0.5079 Remote Similarity NPC20472
0.507 Remote Similarity NPC258035

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC242893 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
0.537 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