Natural Product: NPC133600

Natural Product IDNPC133600
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Ligustilide
IUPAC Name (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one
Synonyms (Z)-Ligustilide
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL481246
PubChem CID 5319022
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0003408] Isobenzofurans

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 IQVQXVFMNOFTMU-FLIBITNWSA-N
Standard InCHI InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-
SMILES CCC/C=C/1OC(=O)C2=C1CCC=C2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   190.1 Volume:   206.03
?
Van der Waals volume.
Dense:   0.923 LogP:   2.792
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.53
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.998
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   12.0
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:   0.626 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.386 Fsp3:   0.417
MCE-18:   12.353
?
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:   0.332 Fluc inhibitor:   0.193
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.449
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.242
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.999 Promiscuous compounds:   0.28

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.738 MDCK Permeability:   -4.759
Pgp-inhibitor:   0.609 Pgp-substrate:   0.004
PAMPA:   0.101
?
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):   0.698
20% Bioavailability (F20%):   0.19 30% Bioavailability (F30%):   0.858
50% Bioavailability (F50%):   0.522

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.612 MRP1:   0.313
Plasma Protein Binding (PPB):   98.626% Volume Distribution (VD):   -0.145
Fu: 1.126%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.98
OATP1B3 inhibitor:   0.993 BCRP inhibitor:   0.013
BSEP inhibitor:   0.955

ADMET: Metabolism

CYP1A2-inhibitor:   0.082 CYP1A2-substrate:   0.995
CYP2C19-inhibitor:   0.447 CYP2C19-substrate:   0.972
CYP2C9-inhibitor:   0.954 CYP2C9-substrate:   0.556
CYP2D6-inhibitor:   0.264 CYP2D6-substrate:   0.427
CYP3A4-inhibitor:   0.001 CYP3A4-substrate:   0.873
CYP2B6-substrate:   0.02 CYP2C8-inhibitor:   1.0
HLM stability:   0.962
?
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):  5.773 Half-life (T1/2):  0.999

ADMET: Toxicity

hERG Blockers:  0.012 hERG Blockers (10um):  0.297
Human Hepatotoxicity (H-HT):  0.938 Drug-induced Liver Injury (DILI):  0.882
AMES Toxicity:  0.587 Rat Oral Acute Toxicity:  0.113
Maximum Recommended Daily Dose:  0.369 Skin Sensitization:  1.0
Carcinogencity:  0.533 Eye Corrosion:  0.998
Eye Irritation:  0.999 Respiratory Toxicity:  0.763
Drug-induced Neurotoxicity:  0.135 Ototoxicity:  0.149
Hematotoxicity:  0.214 Drug-induced Nephrotoxicity:  0.734
Genotoxicity:  0.03 RPMI-8226 Immunitoxicity:  0.103
A549 Cytotoxicity:  0.04 Hek293 Cytotoxicity:  0.038
BCF:   1.356
?
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:   3.955
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.233
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.851
?
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
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]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[20121210]
NPO16118 Ligusticum porteri Species Apiaceae Eukaryota n.a. root n.a. PMID[20879744]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. sclerotium n.a. PMID[21250700]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
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]
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]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[36014481]
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]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[37471031]
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]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. root n.a. PMID[9987830]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO16118 Ligusticum porteri Species Apiaceae 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]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO19048 Pinellia ternata Species Araceae 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]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
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]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9662 Conioselinum vaginatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO30540 Ligusticum brachylobum 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]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. pericarp n.a. PMID[p25172756]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19649 Akebia quinata Species Lardizabalaceae 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]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2727 Actaea simplex Species Ranunculaceae 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]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22033 Cnidium officinale Species 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]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19649 Akebia quinata Species Lardizabalaceae 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]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO19048 Pinellia ternata Species Araceae 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]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO22033 Cnidium officinale Species Apiaceae 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]
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]
NPO15890 Cimicifuga foetida Species Ranunculaceae 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]
NPO11170 Akebia trifoliata Species Lardizabalaceae 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]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16118 Ligusticum porteri Species Apiaceae 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
NPO14951 Zanthoxylum acanthopodium Oil Leaves 0.6 n.a. n.a. % PMID[37471031]
NPO14951 Zanthoxylum acanthopodium Oil Stems n.a. n.a. % PMID[37471031]
NPO15462 Angelica sinensis Oil n.a. 26.92 n.a. n.a. % PMID[36838931]
NPO15462 Angelica sinensis Oil n.a. 3.95 n.a. n.a. % PMID[36838931]
NPO15462 Angelica sinensis Oil n.a. 80.71 ± 4.28 n.a. n.a. % PMID[37480748]
NPO25369 Levisticum officinale Other Root 118.25 21.5 215 mg/100g Database [DUKE]
NPO31073 Ligusticum chuanxiong Oil n.a. 47.57 n.a. n.a. % PMID[37656744]
NPO31073 Ligusticum chuanxiong Oil n.a. 0.71 n.a. n.a. % PMID[37656744]
NPO59106 Vicatia thibetica Oil n.a. 2.76 n.a. n.a. % PMID[36838931]
NPO59106 Vicatia thibetica Oil n.a. 0.15 n.a. n.a. % PMID[36838931]
NPO59106 Vicatia thibetica Oil n.a. 0.79 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
NPT1785 Individual protein Serotonin 7 (5-HT7) receptor Homo sapiens Inhibition = 33.0 % PMID[16643021]
NPT346 Individual protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 44000.0 nM PMID[23993334]
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 107.47 % PMID[23571415]
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 117.75 % PMID[23571415]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 3.022 % DOI[10.6019/CHEMBL4495564]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = -1.23 % 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 = 39.48 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1367 Organism Bemisia tabaci Bemisia tabaci RatioLC50 = 0.9 n.a. PMID[21728333]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 1.26 % DOI[10.21203/rs.3.rs-23951/v1]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.04 % DOI[10.6019/CHEMBL4495565]
NPT4532 Organism Anopheles stephensi Anopheles stephensi Ratio = 0.66 n.a. PMID[19113871]
NPT1381 Organism Aedes aegypti Aedes aegypti Ratio = 0.79 n.a. PMID[19113871]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae GI = 7.5 % PMID[19113871]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae GI = 5.5 % PMID[19113871]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 7.0 % PMID[19113871]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 5.0 % PMID[19113871]
NPT2241 Organism Glomerella acutata Glomerella acutata GI = 6.5 % PMID[19113871]
NPT2241 Organism Glomerella acutata Glomerella acutata GI = 4.5 % PMID[19113871]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster Ratio < 0.07 n.a. PMID[15998112]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster RatioLC50 = 0.009 n.a. PMID[15998112]

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[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 25.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 7.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -8.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 40.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 14.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -3.5 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -16.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 13.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 17.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -14.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -6.3 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 17.1 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -19.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -12.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 2.1 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -15.6 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = -10.0 % PMID[20879744]
NPT32 Organism Mus musculus Mus musculus Activity = 6.5 % PMID[20879744]





 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
- Drosophila melanogaster LC50 = 2540000.0 nM PMID[15998112]
- Drosophila melanogaster LD50 > 50.0 ug PMID[15998112]
- Bemisia tabaci LC50 = 268.4 ppm PMID[21728333]
- Bemisia tabaci LC50 = 254.4 ppm PMID[21728333]

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 NPC133600 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
NPC

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC133600 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