Natural Product: NPC233282

Natural Product IDNPC233282
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Benzyl Salicylate
IUPAC Name benzyl 2-hydroxybenzoate
Synonyms Benzyl Salicylate
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL460124
PubChem CID 8363
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters
            • [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

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 ZCTQGTTXIYCGGC-UHFFFAOYSA-N
Standard InCHI InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
SMILES O=C(c1ccccc1O)OCc1ccccc1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   228.08 Volume:   241.503
?
Van der Waals volume.
Dense:   0.944 LogP:   3.691
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.276
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.457
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   13.0
TPSA:   46.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   1.0 Rings:   2.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.821 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.444 Fsp3:   0.071
MCE-18:   10.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.048 Fluc inhibitor:   0.353
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.127
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.268
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.987 Promiscuous compounds:   0.632

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.065 MDCK Permeability:   -4.554
Pgp-inhibitor:   0.537 Pgp-substrate:   0.001
PAMPA:   0.194
?
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):   0.021
20% Bioavailability (F20%):   0.223 30% Bioavailability (F30%):   0.864
50% Bioavailability (F50%):   0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.344 MRP1:   0.608
Plasma Protein Binding (PPB):   98.51% Volume Distribution (VD):   -0.788
Fu: 1.122%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.964
OATP1B3 inhibitor:   0.995 BCRP inhibitor:   0.012
BSEP inhibitor:   0.948

ADMET: Metabolism

CYP1A2-inhibitor:   0.021 CYP1A2-substrate:   0.999
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.779
CYP2C9-inhibitor:   0.084 CYP2C9-substrate:   0.002
CYP2D6-inhibitor:   0.209 CYP2D6-substrate:   0.005
CYP3A4-inhibitor:   0.035 CYP3A4-substrate:   0.086
CYP2B6-substrate:   0.002 CYP2C8-inhibitor:   0.997
HLM stability:   0.357
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  4.844 Half-life (T1/2):  0.658

ADMET: Toxicity

hERG Blockers:  0.12 hERG Blockers (10um):  0.79
Human Hepatotoxicity (H-HT):  0.025 Drug-induced Liver Injury (DILI):  0.161
AMES Toxicity:  0.122 Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.223 Skin Sensitization:  0.634
Carcinogencity:  0.513 Eye Corrosion:  0.133
Eye Irritation:  0.994 Respiratory Toxicity:  0.271
Drug-induced Neurotoxicity:  0.178 Ototoxicity:  0.048
Hematotoxicity:  0.006 Drug-induced Nephrotoxicity:  0.022
Genotoxicity:  0.012 RPMI-8226 Immunitoxicity:  0.056
A549 Cytotoxicity:  0.097 Hek293 Cytotoxicity:  0.447
BCF:   0.943
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.246
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.94
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.736
?
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
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11014261]
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[15387653]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[17711348]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[19919067]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China 2007-JUN PMID[20550196]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[22325941]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[24328302]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24471493]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota Buds n.a. n.a. PMID[25927817]
NPO12498 Carpesium cernuum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27668963]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28116906]
NPO52048 Inula viscosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[30874370]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota Bark n.a. n.a. PMID[33151073]
NPO12498 Carpesium cernuum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[33810440]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[34684884]
NPO44665 Achillea coarctata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[36006860]
NPO56320 Pinus ponderosa var. ponderosa Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[36080426]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[36364159]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[36401242]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. PMID[36675004]
NPO54216 Pinus contorta subsp. latifolia Genus Pinaceae Eukaryota n.a. n.a. n.a. PMID[36985451]
NPO54547 Pseudotsuga menziesii var. glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[36985451]
NPO55295 Salvia aratocensis Genus Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37241803]
NPO9773 Sideritis raeseri Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37509192]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. PMID[37570937]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. PMID[37759401]
NPO47051 Ononis aurasiaca Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[37971903]
NPO52048 Inula viscosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38245842]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. PMID[38612781]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[38794396]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[39459015]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. aerial part n.a. PMID[7764590]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24329 Primula farinosa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24216 Lolium perenne Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO52048 Inula viscosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9773 Sideritis raeseri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23957 Helleborus caucasicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12498 Carpesium cernuum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23916 Anthocleista grandiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17647 Schkuhria multiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO44665 Achillea coarctata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12498 Carpesium cernuum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24329 Primula farinosa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18952 Sambucus nigra Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20617 Tilletia laevis Species Tilletiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24216 Lolium perenne Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23916 Anthocleista grandiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23957 Helleborus caucasicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17647 Schkuhria multiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16234 Orgyia australis postica Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24173 Plutella xylostella Species Plutellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9773 Sideritis raeseri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3689 Cinnamomum verum Species Lauraceae 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
NPO12498 Carpesium cernuum Oil n.a. 0.1 n.a. n.a. % PMID[33810440]
NPO18952 Sambucus nigra Oil Flowers 0.5 n.a. n.a. % PMID[37759401]
NPO18952 Sambucus nigra Oil Flowers 0.7 n.a. n.a. % PMID[37759401]
NPO19162 Tsuga heterophylla Oil Leaves 0.1 n.a. n.a. % PMID[38794396]
NPO21410 Populus balsamifera Ether extract Leaves 1.89 n.a. n.a. % PMID[38612781]
NPO3689 Cinnamomum verum Oil Leaves 0.03 n.a. n.a. % PMID[36364159]
NPO3689 Cinnamomum verum Oil Leaves 0.15 n.a. n.a. % PMID[36364159]
NPO3689 Cinnamomum verum Oil Leaves 0.02 n.a. n.a. % PMID[36364159]
NPO44665 Achillea coarctata Oil n.a. 0.1 n.a. n.a. % PMID[36006860]
NPO44665 Achillea coarctata Oil n.a. 0.2 n.a. n.a. % PMID[36006860]
NPO44665 Achillea coarctata Oil n.a. 0.9 n.a. n.a. % PMID[36006860]
NPO44665 Achillea coarctata Oil n.a. 0.4 n.a. n.a. % PMID[36006860]
NPO47051 Ononis aurasiaca Oil n.a. 1.3 n.a. n.a. % PMID[37971903]
NPO52048 Inula viscosa Oil n.a. 3.5 n.a. n.a. % PMID[30874370]
NPO52048 Inula viscosa Oil n.a. 0.5 n.a. n.a. % PMID[30874370]
NPO52048 Inula viscosa Oil n.a. 0.3 n.a. n.a. % PMID[30874370]
NPO52048 Inula viscosa Oil n.a. 0.4 n.a. n.a. % PMID[30874370]
NPO54216 Pinus contorta subsp. latifolia Oil Leaves 0.3 n.a. n.a. % PMID[36985451]
NPO54216 Pinus contorta subsp. latifolia Oil Leaves 0.1 n.a. n.a. % PMID[36985451]
NPO54547 Pseudotsuga menziesii var. glauca Oil Leaves 0.4 n.a. n.a. % PMID[36985451]
NPO54547 Pseudotsuga menziesii var. glauca Oil Leaves 0.1 n.a. n.a. % PMID[36985451]
NPO55295 Salvia aratocensis Microwave-assisted hydrodistillation n.a. ± n.a. n.a. % PMID[37241803]
NPO55295 Salvia aratocensis Steam distillation n.a. 0.50 n.a. n.a. % PMID[37241803]
NPO56320 Pinus ponderosa var. ponderosa Oil n.a. 0.1 n.a. n.a. % PMID[36080426]
NPO9348 Cananga odorata Oil n.a. 4.70 n.a. n.a. % PMID[39459015]
NPO9348 Cananga odorata Oil n.a. 1.18 n.a. n.a. % PMID[39459015]
NPO9773 Sideritis raeseri Oil n.a. 0.05 n.a. n.a. % PMID[37509192]

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. 54578.2 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT106 Individual protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 54578.2 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 54947.7 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 19365.1 nM PubChem BioAssay data set
NPT163 Individual protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 56234.1 nM PubChem BioAssay data set
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 47307.9 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 145.8 nM PubChem BioAssay data set
NPT103 Individual protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 13333.2 nM PubChem BioAssay data set
NPT50 Individual protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 31622.8 nM PubChem BioAssay data set
NPT50 Individual protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 79432.8 nM PubChem BioAssay data set
NPT98 Individual protein HERG Homo sapiens Potency n.a. 39810.7 nM PubChem BioAssay data set
NPT46 Individual protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 5011.9 nM PubChem BioAssay data set
NPT532 Individual protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 32629.4 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus EC50 = 0.025 g/m2 PMID[12762809]
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 25.0 % PMID[23490158]
NPT2 Others Unspecified n.a. Potency n.a. 61237.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 5494.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 27111.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 76411.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 54578.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 30899.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 68101.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 19193.7 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. 1089 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 9619.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 12197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 19496.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 7695.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 7641.1 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 17106.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency = 31622.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = -34.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = -29.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 29.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 46.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 25.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 78.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 74.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 65.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 94.0 % PMID[21291237]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 99.0 % PMID[21291237]
NPT2 Others Unspecified n.a. Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 15848.9 nM PubChem BioAssay data set

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus pLD50 = 7.71 n.a. DOI[10.1007/s00044-009-9162-3]





 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 LEL = 3.7 mg/kg-day ToxVal
- Rattus norvegicus LD50 = 2227.0 mg/kg ToxVal
- Rattus norvegicus NOAEL = 5.0 mg/kg-day ToxVal
- Mus musculus LEL = 11.1 mg/kg-day ToxVal
- Oryctolagus cuniculus LD50 = 14150.0 mg/kg ToxVal
- Homo sapiens DNEL systemic = 7.8 mg/m3 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 NPC233282 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
0.6286 Remote Similarity NPC128825
0.6279 Remote Similarity NPC12694
0.6154 Remote Similarity NPC164149
0.6136 Remote Similarity NPC4164
0.5833 Remote Similarity NPC118343
0.5789 Remote Similarity NPC94637
0.5227 Remote Similarity NPC610880

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC233282 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
0.6286 Remote Similarity NPD9493 Phase 4
0.5833 Remote Similarity NPD1238 Phase 4

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