Structure

Physi-Chem Properties

Molecular Weight:  320.05
Volume:  300.33
LogP:  4.339
LogD:  3.535
LogS:  -6.398
# Rotatable Bonds:  2
TPSA:  68.9
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.577
Synthetic Accessibility Score:  2.54
Fsp3:  0.188
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.883
MDCK Permeability:  1.7469250451540574e-05
Pgp-inhibitor:  0.113
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.017
Plasma Protein Binding (PPB):  95.27338409423828%
Volume Distribution (VD):  0.657
Pgp-substrate:  6.726668834686279%

ADMET: Metabolism

CYP1A2-inhibitor:  0.96
CYP1A2-substrate:  0.97
CYP2C19-inhibitor:  0.882
CYP2C19-substrate:  0.427
CYP2C9-inhibitor:  0.816
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.615
CYP2D6-substrate:  0.894
CYP3A4-inhibitor:  0.452
CYP3A4-substrate:  0.163

ADMET: Excretion

Clearance (CL):  5.357
Half-life (T1/2):  0.273

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.383
Drug-inuced Liver Injury (DILI):  0.957
AMES Toxicity:  0.347
Rat Oral Acute Toxicity:  0.087
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.602
Carcinogencity:  0.035
Eye Corrosion:  0.538
Eye Irritation:  0.977
Respiratory Toxicity:  0.652

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC43792

Natural Product ID:  NPC43792
Common Name*:   CQEQTGQGSHCEQL-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CQEQTGQGSHCEQL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H13ClO5/c1-7-13-9-4-8(20-2)5-10(18)14(9)16(19)22-11(13)6-12(21-3)15(7)17/h4-6,18H,1-3H3
SMILES:  Cc1c2c3cc(cc(c3c(=O)oc2cc(c1Cl)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11500722
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[10364842]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[12392098]
NPO16914 Abacopteris penangiana n.a. n.a. n.a. n.a. rhizome n.a. PMID[16499328]
NPO16914 Abacopteris penangiana n.a. n.a. n.a. Rhizomes n.a. n.a. PMID[16499328]
NPO16914 Abacopteris penangiana n.a. n.a. n.a. aerial parts Jiangxi Province, China 2004-JUN PMID[17922550]
NPO21717 Acremonium chrysogenum Species n.a. Eukaryota n.a. n.a. n.a. PMID[23089729]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24996657]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[25767328]
NPO1816 Pterogorgia citrina Species Gorgoniidae Eukaryota n.a. Caribbean n.a. PMID[7911157]
NPO12178 Pinellia pedatisecta Species Araceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12178 Pinellia pedatisecta Species Araceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17598 Maytenus mossambicensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12178 Pinellia pedatisecta Species Araceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3210 Polyporus arcularius Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21752.1 Bauhinia forficata subsp. pruinosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO309 Phyla canescens Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16559 Darwinia grandiflora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15728 Prunus nipponica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17598 Maytenus mossambicensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12178 Pinellia pedatisecta Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14792 Abies grandis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12400 Cereus gummosus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16689 Corydalis clavicula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10736 Teucrium kotschyanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21717 Acremonium chrysogenum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17137 Nymania capensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16208 Viguiera pinnatiloba Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1816 Pterogorgia citrina Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16914 Abacopteris penangiana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO814 Acipenser sturio Species Acipenseridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22249 Senecio leptolobus Species Asteraceae 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 NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC43792 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC43792 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  Bioactivity similarity: Similar Natural Products in NPASS

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