Structure

Physi-Chem Properties

Molecular Weight:  246.13
Volume:  264.072
LogP:  3.824
LogD:  3.425
LogS:  -3.691
# Rotatable Bonds:  3
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.644
Synthetic Accessibility Score:  3.027
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.784
MDCK Permeability:  1.837221861933358e-05
Pgp-inhibitor:  0.661
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.502
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.529
Plasma Protein Binding (PPB):  90.51956939697266%
Volume Distribution (VD):  0.942
Pgp-substrate:  6.980719566345215%

ADMET: Metabolism

CYP1A2-inhibitor:  0.921
CYP1A2-substrate:  0.9
CYP2C19-inhibitor:  0.744
CYP2C19-substrate:  0.405
CYP2C9-inhibitor:  0.305
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.587
CYP2D6-substrate:  0.894
CYP3A4-inhibitor:  0.179
CYP3A4-substrate:  0.197

ADMET: Excretion

Clearance (CL):  10.612
Half-life (T1/2):  0.715

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.173
Drug-inuced Liver Injury (DILI):  0.161
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.072
Maximum Recommended Daily Dose:  0.948
Skin Sensitization:  0.471
Carcinogencity:  0.092
Eye Corrosion:  0.022
Eye Irritation:  0.841
Respiratory Toxicity:  0.675

Download Data

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

  Natural Product: NPC129239

Natural Product ID:  NPC129239
Common Name*:   QTXBUQHQOMWGJN-SNVBAGLBSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QTXBUQHQOMWGJN-SNVBAGLBSA-N
Standard InCHI:  InChI=1S/C15H18O3/c1-9(2)10-4-5-11-6-12(16)8-14(13(11)7-10)15(17)18-3/h6,8,10,16H,1,4-5,7H2,2-3H3/t10-/m1/s1
SMILES:  C=C(C)[C@@H]1CCc2cc(cc(c2C1)C(=O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10490645
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0001871] Naphthalenecarboxylic acids 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
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/COM-96-7609.]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[10705751]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. seed n.a. PMID[12822897]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[16038566]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. stem n.a. PMID[16964757]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[18064621]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[18064621]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[18081254]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. rhizome n.a. PMID[23059629]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[24257774]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26517152]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3691 Albizia mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10901 Tessaria dodoneaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4944 Bactris plumeriana Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1380 Phylica rogersii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18088 Euglena longa Species Euglenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3817 Chrysosporium queenslandicum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7529 Viscum multinerve Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4851 Penstemon confertus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4484 Maytenus obtusifolia Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3315 Eucalyptus hybr Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2343 Haplopappus arbutoides 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 NPC129239 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 NPC129239 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