Natural Product: NPC260000

Natural Product IDNPC260000
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Raspberryketone
IUPAC Name 4-(4-hydroxyphenyl)butan-2-one
Synonyms Raspberry Ketone; Raspberryketone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL105912
PubChem CID 21648
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

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 NJGBTKGETPDVIK-UHFFFAOYSA-N
Standard InCHI InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
SMILES CC(=O)CCc1ccc(cc1)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   164.08 Volume:   179.994
?
Van der Waals volume.
Dense:   0.912 LogP:   1.614
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.335
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -0.968
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   7.0
TPSA:   37.3
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   1.0 Rings:   1.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.741 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.649 Fsp3:   0.3
MCE-18:   6.0
?
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:   0.076 Fluc inhibitor:   0.004
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.02
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.997 Promiscuous compounds:   0.083

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.402 MDCK Permeability:   -4.689
Pgp-inhibitor:   0.57 Pgp-substrate:   0.342
PAMPA:   0.367
?
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):   0.003
20% Bioavailability (F20%):   0.139 30% Bioavailability (F30%):   0.138
50% Bioavailability (F50%):   0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.057 MRP1:   0.356
Plasma Protein Binding (PPB):   95.955% Volume Distribution (VD):   -0.212
Fu: 4.386%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.747
OATP1B3 inhibitor:   0.857 BCRP inhibitor:   0.093
BSEP inhibitor:   0.984

ADMET: Metabolism

CYP1A2-inhibitor:   0.367 CYP1A2-substrate:   0.039
CYP2C19-inhibitor:   0.812 CYP2C19-substrate:   0.036
CYP2C9-inhibitor:   0.788 CYP2C9-substrate:   0.008
CYP2D6-inhibitor:   0.962 CYP2D6-substrate:   0.176
CYP3A4-inhibitor:   0.002 CYP3A4-substrate:   0.012
CYP2B6-substrate:   0.005 CYP2C8-inhibitor:   0.745
HLM stability:   0.285
?
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):  10.597 Half-life (T1/2):  1.055

ADMET: Toxicity

hERG Blockers:  0.117 hERG Blockers (10um):  0.546
Human Hepatotoxicity (H-HT):  0.516 Drug-induced Liver Injury (DILI):  0.044
AMES Toxicity:  0.224 Rat Oral Acute Toxicity:  0.104
Maximum Recommended Daily Dose:  0.282 Skin Sensitization:  0.941
Carcinogencity:  0.476 Eye Corrosion:  0.941
Eye Irritation:  0.995 Respiratory Toxicity:  0.419
Drug-induced Neurotoxicity:  0.662 Ototoxicity:  0.376
Hematotoxicity:  0.289 Drug-induced Nephrotoxicity:  0.468
Genotoxicity:  0.03 RPMI-8226 Immunitoxicity:  0.026
A549 Cytotoxicity:  0.016 Hek293 Cytotoxicity:  0.142
BCF:   0.683
?
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:   2.494
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.421
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.891
?
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
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s00709-015-0790-9]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. DOI[10.1021/ja107190w]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. callus n.a. PMID[10552648]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. Japan n.a. PMID[12542351]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[16755060]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[17666848]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. leaf n.a. PMID[18214349]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[18239311]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19785430]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19962306]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20078074]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. seed n.a. PMID[21049975]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[21550801]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[23707257]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota whole plants Nanning District, Guangxi Province, China 2012-Sep PMID[25647077]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota aerial parts Seoul, Korea n.a. PMID[26331882]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[32872604]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[36352904]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36840093]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[37152127]
NPO58210 Anthemis palestina Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38005810]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38719900]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39679248]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39680258]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[6705789]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13700 Streptomyces nobilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13983 Acer maximowiczianum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2318 Stellaria holostea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4216 Dalbergia assamica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15639 Dasycladus vermicularis Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14851 Lantana montevidensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14543 Mycena sanguinolenta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hay n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hull Husk n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13983 Acer maximowiczianum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13210 Echinops transiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14851 Lantana montevidensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13983 Acer maximowiczianum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4216 Dalbergia assamica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15260 Senecio suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13700 Streptomyces nobilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14543 Mycena sanguinolenta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22207 Polyporus pini Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15639 Dasycladus vermicularis Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9125 Haemanthus amarylloides Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15502 Muscari botryoides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7988.1 Fraxinus angustifolia subsp. oxycarpa Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8435 Hedysarum theinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15384 Olearia pimeleoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2318 Stellaria holostea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference
NPO58210 Anthemis palestina Oil n.a. 0.29 n.a. n.a. % PMID[38005810]
NPO58210 Anthemis palestina Shade-dried n.a. 0.33 n.a. n.a. % PMID[38005810]
NPO58210 Anthemis palestina Sun-dried n.a. 1.53 n.a. n.a. % PMID[38005810]
NPO58210 Anthemis palestina Oven-dried n.a. 0.50 n.a. n.a. % PMID[38005810]
NPO58210 Anthemis palestina Oven-dried n.a. 0.38 n.a. n.a. % PMID[38005810]
NPO58210 Anthemis palestina Microwaved-dried n.a. 0.70 n.a. n.a. % PMID[38005810]
NPO5954 Petroselinum crispum Oil n.a. 0.56±0.05 n.a. n.a. % PMID[38719900]

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
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 6164.5 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens IC50 = 252000.0 nM PMID[20226658]
NPT153 Individual protein Androgen Receptor Homo sapiens IC50 = 251188.64 nM PMID[20226658]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell line K562 Homo sapiens IC50 > 100000.0 nM DOI[10.1016/S0960-894X(97)10147-0]
NPT76 Cell line C6 Rattus norvegicus Activity = 106.8 % PMID[21353549]
NPT76 Cell line C6 Rattus norvegicus Activity = 100.9 % PMID[21353549]
NPT2 Others Unspecified n.a. Potency n.a. 2730.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 15355.3 nM PubChem BioAssay data set

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
- Rattus norvegicus LD50 = 1320.0 mg/kg ToxVal
- Rattus norvegicus NOAEL = 128.0 mg/kg-day ToxVal
- Homo sapiens DNEL systemic = 114.24 mg/m3 ToxVal
- Bos taurus LEL = 250.0 mg/kg-day ToxVal
- Gallus gallus domesticus LEL = 250.0 mg/kg-day ToxVal
- Sus scrofa domesticus LEL = 250.0 mg/kg-day 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 NPC260000 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
0.7419 Intermediate Similarity NPC188677
0.6857 Remote Similarity NPC29989
0.6786 Remote Similarity NPC608485
0.6389 Remote Similarity NPC261573
0.6333 Remote Similarity NPC280869
0.6333 Remote Similarity NPC23167
0.6154 Remote Similarity NPC49529
0.6053 Remote Similarity NPC177576
0.6 Remote Similarity NPC74458
0.5938 Remote Similarity NPC138117
0.5938 Remote Similarity NPC325292
0.5938 Remote Similarity NPC242240
0.5854 Remote Similarity NPC317305
0.5789 Remote Similarity NPC299406
0.5714 Remote Similarity NPC197783
0.561 Remote Similarity NPC69332
0.5588 Remote Similarity NPC123273
0.5588 Remote Similarity NPC318325
0.5556 Remote Similarity NPC113460
0.5476 Remote Similarity NPC120693
0.5476 Remote Similarity NPC88141
0.5476 Remote Similarity NPC321252
0.5476 Remote Similarity NPC252544
0.5349 Remote Similarity NPC70843
0.5349 Remote Similarity NPC86198
0.5294 Remote Similarity NPC298224
0.5278 Remote Similarity NPC257390
0.5278 Remote Similarity NPC25493
0.525 Remote Similarity NPC610758
0.5227 Remote Similarity NPC95178
0.5227 Remote Similarity NPC265454
0.5227 Remote Similarity NPC63345
0.5217 Remote Similarity NPC123228
0.5217 Remote Similarity NPC123722
0.5161 Remote Similarity NPC258219
0.5143 Remote Similarity NPC91461
0.5143 Remote Similarity NPC7686
0.5143 Remote Similarity NPC40258
0.5128 Remote Similarity NPC280347
0.5128 Remote Similarity NPC242895
0.5128 Remote Similarity NPC133909
0.5128 Remote Similarity NPC600565
0.5111 Remote Similarity NPC8931
0.5111 Remote Similarity NPC277394

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC260000 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