Natural Product: NPC161617

Natural Product IDNPC161617
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 2,4-Dihydroxyacetophenone
IUPAC Name 1-(2,4-dihydroxyphenyl)ethanone
Synonyms 2,4-Dihydroxy Acetophenone; 2,4-Dihydroxyacetophenone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL243374
PubChem CID 6990
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003670] Aryl ketones
              • [CHEMONTID:0004296] Phenylketones
                • [CHEMONTID:0004298] Alkyl-phenylketones

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 SULYEHHGGXARJS-UHFFFAOYSA-N
Standard InCHI InChI=1S/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H3
SMILES Oc1ccc(c(c1)O)C(=O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   152.05 Volume:   154.193
?
Van der Waals volume.
Dense:   0.986 LogP:   1.142
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.249
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.465
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   7.0
TPSA:   57.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   2.0 Rings:   1.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.596 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.888 Fsp3:   0.125
MCE-18:   7.0
?
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:   0.226 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.093
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.0
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.998 Promiscuous compounds:   0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.737 MDCK Permeability:   -4.762
Pgp-inhibitor:   0.167 Pgp-substrate:   0.261
PAMPA:   0.335
?
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):   0.037
20% Bioavailability (F20%):   0.199 30% Bioavailability (F30%):   0.505
50% Bioavailability (F50%):   0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.218 MRP1:   0.772
Plasma Protein Binding (PPB):   88.095% Volume Distribution (VD):   -0.355
Fu: 13.113%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.894
OATP1B3 inhibitor:   0.971 BCRP inhibitor:   0.383
BSEP inhibitor:   0.099

ADMET: Metabolism

CYP1A2-inhibitor:   0.951 CYP1A2-substrate:   0.974
CYP2C19-inhibitor:   0.016 CYP2C19-substrate:   0.43
CYP2C9-inhibitor:   0.108 CYP2C9-substrate:   0.977
CYP2D6-inhibitor:   0.847 CYP2D6-substrate:   0.443
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.021
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.998
HLM stability:   0.909
?
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):  2.902 Half-life (T1/2):  1.797

ADMET: Toxicity

hERG Blockers:  0.055 hERG Blockers (10um):  0.481
Human Hepatotoxicity (H-HT):  0.388 Drug-induced Liver Injury (DILI):  0.14
AMES Toxicity:  0.439 Rat Oral Acute Toxicity:  0.158
Maximum Recommended Daily Dose:  0.293 Skin Sensitization:  0.766
Carcinogencity:  0.488 Eye Corrosion:  0.843
Eye Irritation:  0.999 Respiratory Toxicity:  0.765
Drug-induced Neurotoxicity:  0.232 Ototoxicity:  0.162
Hematotoxicity:  0.162 Drug-induced Nephrotoxicity:  0.1
Genotoxicity:  0.557 RPMI-8226 Immunitoxicity:  0.058
A549 Cytotoxicity:  0.091 Hek293 Cytotoxicity:  0.403
BCF:   1.095
?
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:   3.309
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.014
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.42
?
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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)80275-7]
NPO27831 Phakellia flabellata Species Bubaridae Eukaryota n.a. n.a. n.a. DOI[10.1021/jo00445a028]
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]
NPO8809 Cynanchum wilfordii Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[10217732]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota Roots n.a. n.a. PMID[11374953]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15056914]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15270557]
NPO25999 Ferula communis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15620264]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16644212]
NPO280 Dysidea chlorea Species Dysideidae Eukaryota n.a. Okinawan n.a. PMID[16872148]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[17488128]
NPO27850 Trichilia catigua Species Meliaceae Eukaryota n.a. bark n.a. PMID[18020420]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[19534474]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[19948405]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[20121210]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20415462]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota roots Whitessence Srl, Viterbo, Italy 2005-OCT PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. seed n.a. PMID[23672042]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24024763]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota Roots n.a. n.a. PMID[24054487]
NPO55 Croton urucurana Species Euphorbiaceae Eukaryota n.a. twig n.a. PMID[24354204]
NPO55 Croton urucurana Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[24354204]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24412339]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO55 Croton urucurana Species Euphorbiaceae Eukaryota Latex n.a. n.a. PMID[26561866]
NPO8809 Cynanchum wilfordii Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26716755]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[28558206]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[32031796]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds DingXi, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds LanZhou, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China Maturation PMID[33131958]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[36483735]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36838931]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37480748]
NPO28333 Syzygium levinei Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[38005226]
NPO62416 Phoebe zhennan Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[38595765]
NPO26953 Hebeloma senescens Species Cortinariaceae Eukaryota fruiting bodies n.a. n.a. PMID[7561908]
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]
NPO26455 Merwilla natalensis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO28176 Russula lepida Species Russulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25999 Ferula communis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27973 Simaba cuneata Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26809 Synoicum blochmanni Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27918 Pterocarpus macrocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO280 Dysidea chlorea Species Dysideidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29373 Trichoplusia ni Species Noctuidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2641 Marsupella aquatica Species Gymnomitriaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5745 Randia formosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27850 Trichilia catigua Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6086 Axinella polypoides Species Axinellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6312 Picea engelmannii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28228 Kielmeyera rubriflora Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4538 Paysonia densipila Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3834 Periplaneta americana Species Blattoidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26953 Hebeloma senescens Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28507 Hymenoxys grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28543 Alcyonium coralloides Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28425 Senecio miser Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8276 Harpullia ramiflora Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26214 Baccharis artemisioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8942 Hedysarum coronarium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7220 Artemisia latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28525 Urginea riparia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28494 Hydroclathrus tenuis Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28214 Phyllosticta cirsii Species Phyllostictaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14547.1 Ilex pubescens var. glaber Varieties Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7170 Tylophora ovata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7170 Tylophora ovata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24694 Vincetoxicum pycnostelma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14547.1 Ilex pubescens var. glaber Varieties Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28507 Hymenoxys grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5745 Randia formosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28176 Russula lepida Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8680 Polypodium niponicum Species Polypodiaceae 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]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14547.1 Ilex pubescens var. glaber Varieties Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2727 Actaea simplex Species Ranunculaceae 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]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO842 Vincetoxicum versicolor Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8809 Cynanchum wilfordii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24694 Vincetoxicum pycnostelma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28214 Phyllosticta cirsii Species Phyllostictaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28479 Campanula hypopolia Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29373 Trichoplusia ni Species Noctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28461 Crepis czerepanovii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28404 Chasmanthera dependens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28176 Russula lepida Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27973 Simaba cuneata Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6086 Axinella polypoides Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO55 Croton urucurana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11786 Cylindropuntia leptocaulis Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28593 Pteris pedata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25999 Ferula communis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27891 Lethariella sinensis Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28009 Pellina semitubulosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27850 Trichilia catigua Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28333 Syzygium levinei Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26214 Baccharis artemisioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28651 Othonna tagetes Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26953 Hebeloma senescens Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28443 Larix lyallii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28228 Kielmeyera rubriflora Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27956 Eupatoriastrum nelsonii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28543 Alcyonium coralloides Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10135 Tripteris microcarpa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10658 Pedicularis rhinanthoides Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28507 Hymenoxys grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28282 Turbina corymbosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7220 Artemisia latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28071 Dendrobates auratus Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27831 Phakellia flabellata Species Bubaridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9245 Ventilago madraspatana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28316 Scandix pecten-veneris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26455 Merwilla natalensis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28525 Urginea riparia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28611 Phragmatobia fuliginosa Species Erebidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28668 Agave cocui Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8942 Hedysarum coronarium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25330 Maackia floribunda Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27906 Philadelphus coronarius Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27938 Meliosma wightii Species Sabiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3834 Periplaneta americana Species Blattoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25900 Pteris podophylla Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28425 Senecio miser Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1017 Dendrobium gibsonii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28494 Hydroclathrus tenuis Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6312 Picea engelmannii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8809 Cynanchum wilfordii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25823 Haminoea navicula Species Haminoeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4983 Bromelia pinguin Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28100 Jacobaea othonnae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26324 Fevillea cordifolia Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25927 Dictyota dentata Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27918 Pterocarpus macrocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2641 Marsupella aquatica Species Gymnomitriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8531 Centaurea ferox Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23643 Thalictrum aquilegiifolium Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26885 Dictyosphaeria favulosa Species Siphonocladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5745 Randia formosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5486 Helicoon richonis Species Orbiliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO280 Dysidea chlorea Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25874 Tuber borchii Species Tuberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4538 Paysonia densipila Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26809 Synoicum blochmanni Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8276 Harpullia ramiflora Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13333 Paenibacillus thiaminolyticus Species Paenibacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8407 Polyporus fomentarius Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2727 Actaea simplex Species Ranunculaceae 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
NPO62416 Phoebe zhennan Oil n.a. 0.22 n.a. n.a. % PMID[38595765]
NPO62416 Phoebe zhennan Oil n.a. 0.19 n.a. n.a. % PMID[38595765]
NPO62416 Phoebe zhennan Oil n.a. 0.32 n.a. n.a. % PMID[38595765]

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
NPT2875 Individual protein Solute carrier family 28 member 3 Homo sapiens Ki > 100000.0 nM PMID[19097778]
NPT67 Individual protein Cholinesterase Equus caballus Inhibition < 5.0 % PMID[31444085]
NPT66 Individual protein Acetylcholinesterase Electrophorus electricus Inhibition < 5.0 % PMID[29033233]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell line A549 Homo sapiens IC50 > 100000.0 nM PMID[21696954]
NPT306 Cell line PC-3 Homo sapiens IC50 > 100000.0 nM PMID[21696954]
NPT170 Cell line SK-MEL-28 Homo sapiens IC50 > 100000.0 nM PMID[21696954]
NPT114 Cell line LoVo Homo sapiens IC50 = 97000.0 nM PMID[21696954]
NPT22906 Protein complex Urease subunit alpha/Urease subunit beta Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori) Inhibition = 14.0 % PMID[17400458]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[21696954]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 45000.0 nM PMID[21696954]
NPT2 Others Unspecified n.a. Ki = 33.31 nM PMID[18423943]
NPT2 Others Unspecified n.a. Ki = 32.1 nM PMID[18423943]
NPT2 Others Unspecified n.a. IC50 = 700000.0 nM PMID[926120]
NPT2 Others Unspecified n.a. IC50 = 520000.0 nM PMID[926120]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 127.0 % PMID[926120]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 77.0 % PMID[926120]





 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
- Rattus norvegicus LD50 = 2830.0 mg/kg ToxVal

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 NPC161617 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
0.7692 Intermediate Similarity NPC600232
0.6296 Remote Similarity NPC224584
0.6071 Remote Similarity NPC283844
0.5926 Remote Similarity NPC209486
0.5926 Remote Similarity NPC6984
0.5882 Remote Similarity NPC267552
0.5714 Remote Similarity NPC80027
0.5556 Remote Similarity NPC19174
0.5556 Remote Similarity NPC115159
0.5556 Remote Similarity NPC133909
0.5517 Remote Similarity NPC240163
0.5405 Remote Similarity NPC484341
0.5405 Remote Similarity NPC484342
0.5405 Remote Similarity NPC120488
0.5405 Remote Similarity NPC484343
0.5405 Remote Similarity NPC262435
0.5405 Remote Similarity NPC484344
0.5405 Remote Similarity NPC202856
0.5405 Remote Similarity NPC305858
0.5405 Remote Similarity NPC102829
0.5405 Remote Similarity NPC484340
0.5385 Remote Similarity NPC198249
0.5385 Remote Similarity NPC213603
0.5385 Remote Similarity NPC602737
0.5312 Remote Similarity NPC32032
0.5312 Remote Similarity NPC95309
0.5263 Remote Similarity NPC156139
0.5263 Remote Similarity NPC224273
0.5263 Remote Similarity NPC297186
0.5161 Remote Similarity NPC231717
0.5135 Remote Similarity NPC158222
0.5128 Remote Similarity NPC26697
0.5128 Remote Similarity NPC601647

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC161617 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data