Natural Product: NPC83628

Natural Product IDNPC83628
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Rac-3-N-Butylphthalide
IUPAC Name 3-butyl-3H-2-benzofuran-1-one
Synonyms N-Butylphthalide
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL248594
PubChem CID 61361
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans
        • [CHEMONTID:0001578] Benzofuranones

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 HJXMNVQARNZTEE-UHFFFAOYSA-N
Standard InCHI InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3
SMILES CCCCC1OC(=O)c2c1cccc2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   190.1 Volume:   206.03
?
Van der Waals volume.
Dense:   0.923 LogP:   2.778
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.584
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.96
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   11.0
TPSA:   26.3
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   2.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.684 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.557 Fsp3:   0.417
MCE-18:   31.176
?
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:   0.096 Fluc inhibitor:   0.026
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.132
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.197
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.735 Promiscuous compounds:   0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.988 MDCK Permeability:   -4.664
Pgp-inhibitor:   0.439 Pgp-substrate:   0.112
PAMPA:   0.351
?
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):   0.001
20% Bioavailability (F20%):   0.011 30% Bioavailability (F30%):   0.014
50% Bioavailability (F50%):   0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.928 MRP1:   0.935
Plasma Protein Binding (PPB):   98.824% Volume Distribution (VD):   -0.142
Fu: 1.551%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.245
OATP1B3 inhibitor:   0.245 BCRP inhibitor:   0.039
BSEP inhibitor:   0.468

ADMET: Metabolism

CYP1A2-inhibitor:   0.108 CYP1A2-substrate:   0.995
CYP2C19-inhibitor:   0.844 CYP2C19-substrate:   0.979
CYP2C9-inhibitor:   0.018 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.895
CYP3A4-inhibitor:   0.008 CYP3A4-substrate:   0.094
CYP2B6-substrate:   0.862 CYP2C8-inhibitor:   0.955
HLM stability:   0.984
?
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):  4.825 Half-life (T1/2):  1.016

ADMET: Toxicity

hERG Blockers:  0.103 hERG Blockers (10um):  0.612
Human Hepatotoxicity (H-HT):  0.536 Drug-induced Liver Injury (DILI):  0.576
AMES Toxicity:  0.471 Rat Oral Acute Toxicity:  0.247
Maximum Recommended Daily Dose:  0.299 Skin Sensitization:  0.987
Carcinogencity:  0.662 Eye Corrosion:  0.975
Eye Irritation:  0.995 Respiratory Toxicity:  0.378
Drug-induced Neurotoxicity:  0.631 Ototoxicity:  0.168
Hematotoxicity:  0.362 Drug-induced Nephrotoxicity:  0.732
Genotoxicity:  0.05 RPMI-8226 Immunitoxicity:  0.048
A549 Cytotoxicity:  0.076 Hek293 Cytotoxicity:  0.099
BCF:   1.459
?
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:   3.865
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.749
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.558
?
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
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1155/2014/726070]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19778086]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. sclerotium n.a. PMID[21250700]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[25700090]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO52078 Siparuna muricata Species Siparunaceae Eukaryota n.a. n.a. n.a. PMID[34063513]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[34885954]
NPO52078 Siparuna muricata Species Siparunaceae Eukaryota n.a. n.a. n.a. PMID[36671283]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36838931]
NPO59106 Vicatia thibetica 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]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37656744]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38719900]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. root n.a. PMID[9987830]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9662 Conioselinum vaginatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf Wax n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Pt n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9662 Conioselinum vaginatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9662 Conioselinum vaginatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27024 Ligusticopsis brachyloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26721.1 Apium graveolens var. dulce Varieties Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9662 Conioselinum vaginatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18951 Ligusticum sinense Species Apiaceae 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]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae 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
NPO15462 Angelica sinensis Oil n.a. 14.68 n.a. n.a. % PMID[36838931]
NPO15462 Angelica sinensis Oil n.a. 1.44 ± 1.23 n.a. n.a. % PMID[37480748]
NPO25369 Levisticum officinale Other Root 84.4 15.3 153.5 mg/100g Database [DUKE]
NPO26721 Apium graveolens Raw Seed 92 4 180 mg/100g Database [DUKE]
NPO26721 Apium graveolens Oil n.a. 5.36 n.a. n.a. % PMID[34885954]
NPO31073 Ligusticum chuanxiong Oil n.a. 1.39 n.a. n.a. % PMID[37656744]
NPO52078 Siparuna muricata n.a. Leaves 2.94 n.a. n.a. % PMID[36671283]
NPO59106 Vicatia thibetica Oil n.a. 55.22 n.a. n.a. % PMID[36838931]
NPO59106 Vicatia thibetica Oil n.a. 56.96 n.a. n.a. % PMID[36838931]

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
NPT261 Individual protein Monoamine oxidase A Homo sapiens Inhibition = 11.2 % PMID[28131710]
NPT2748 Individual protein Butyrylcholinesterase Rattus norvegicus Inhibition = 2.67 % PMID[32146060]
NPT204 Individual protein Acetylcholinesterase Homo sapiens Inhibition < 5.0 % PMID[33640707]
NPT2748 Individual protein Butyrylcholinesterase Rattus norvegicus Inhibition < 5.0 % PMID[33640707]
NPT2748 Individual protein Butyrylcholinesterase Rattus norvegicus Inhibition < 5.0 % PMID[35183029]
NPT204 Individual protein Acetylcholinesterase Homo sapiens Inhibition < 5.0 % PMID[35183029]
NPT582 Individual protein Monoamine oxidase B Homo sapiens Inhibition = 18.2 % PMID[32146060]
NPT582 Individual protein Monoamine oxidase B Homo sapiens Inhibition = 18.2 % PMID[35183029]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = -47.82 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 4.45 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT66 Individual protein Acetylcholinesterase Electrophorus electricus Inhibition < 5.0 % PMID[33640707]
NPT29389 Protein complex group Glutamate NMDA receptor Rattus norvegicus Ki = 14.8 nM PMID[34710748]
NPT66 Individual protein Acetylcholinesterase Electrophorus electricus Inhibition < 5.0 % PMID[35183029]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT681 Cell line PC-12 Rattus norvegicus Activity = 73.05 % PMID[22827516]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 68.05 % PMID[22827516]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 16.2 U/ml PMID[26189079]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 36.83 U/ml PMID[26189079]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 36.74 U/L PMID[26189079]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 140.79 U/L PMID[26189079]
NPT34 Cell line BV-2 Mus musculus Inhibition = 22.9 % PMID[35183029]
NPT34 Cell line BV-2 Mus musculus Inhibition = 37.2 % PMID[35183029]
NPT34 Cell line BV-2 Mus musculus Inhibition = 27.6 % PMID[35183029]
NPT34 Cell line BV-2 Mus musculus Inhibition = 43.7 % PMID[35183029]
NPT681 Cell line PC-12 Rattus norvegicus Activity = 64.1 % PMID[35183029]
NPT34 Cell line BV-2 Mus musculus Inhibition = 15.2 % PMID[35183029]
NPT34 Cell line BV-2 Mus musculus Inhibition = 13.4 % PMID[35183029]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.2447 n.a. DOI[10.1101/2020.04.21.054387]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM DOI[10.6019/CHEMBL4651402]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM DOI[10.6019/CHEMBL4651402]
NPT28438 Unchecked Unchecked n.a. Activity = 55.71 % PMID[34710748]
NPT28438 Unchecked Unchecked n.a. Activity = 73.45 % PMID[34710748]
NPT28833 No target No relevant target n.a. Activity = 0.21 n.a. PMID[35183029]
NPT28438 Unchecked Unchecked n.a. Activity = 57.94 % PMID[34710748]
NPT28438 Unchecked Unchecked n.a. Inhibition n.a. n.a. % PMID[35183029]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 130060.0 nM PMID[20133025]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 67.8 % PMID[21684163]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 15.72 % PMID[23481646]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 14.1 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 28.06 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 22.95 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 42.45 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 71.01 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 76.6 % PMID[26189079]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 12.95 % PMID[27031213]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 740000.0 nM PMID[27031213]
NPT20967 Cell line Platelet n.a. Inhibition = 17.43 % PMID[22827516]
NPT20967 Cell line Platelet n.a. Inhibition = 9.5 % PMID[22827516]
NPT20967 Cell line Platelet n.a. IC50 = 480000.0 nM PMID[22827516]
NPT20967 Cell line Platelet n.a. IC50 > 1000000.0 nM PMID[22827516]
NPT614 Tissue Plasma Rattus norvegicus IE50 = 169.96 uM/L PMID[17632002]
NPT614 Tissue Plasma Rattus norvegicus IE50 = 14.49 uM/L PMID[17632002]
NPT614 Tissue Plasma Rattus norvegicus Inhibition = 9.5 % PMID[33640707]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Activity = 42.0 % PMID[27012524]
NPT32 Organism Mus musculus Mus musculus Activity = 46.51 pg/g PMID[35931005]
NPT32 Organism Mus musculus Mus musculus Activity = 80.12 pg/g PMID[35931005]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 25.73 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 33.61 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 40.83 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 40.04 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 31.47 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 26.9 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 23.58 % PMID[22827516]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 24.36 % PMID[27031213]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 63.55 % PMID[27031213]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 87.6 % PMID[29202406]
NPT29 Organism Rattus norvegicus Rattus norvegicus Survival = 68.8 % PMID[29202406]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity n.a. n.a. n.a. PMID[35931005]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 1.33 n.a. PMID[36921528]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 82.2 % PMID[36921528]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 48.0 % PMID[35462165]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 13.1 % PMID[33799069]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity n.a. n.a. n.a. PMID[33799069]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 30.0 % PMID[35462165]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 2.13 n.a. PMID[34710748]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 1.64 % PMID[36921528]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 18.81 % PMID[34710748]





 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
- Mus musculus LD50 = 750.89 mg.kg-1 PMID[20133025]

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 NPC83628 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
1.0 High Similarity NPC265407
0.5814 Remote Similarity NPC486646
0.5745 Remote Similarity NPC307651
0.5217 Remote Similarity NPC7012

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC83628 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
0.8824 High Similarity NPD2181 Clinical (unspecified phase)

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