Structure

Physi-Chem Properties

Molecular Weight:  338.08
Volume:  331.968
LogP:  3.309
LogD:  3.176
LogS:  -4.767
# Rotatable Bonds:  5
TPSA:  74.97
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.522
Synthetic Accessibility Score:  2.456
Fsp3:  0.158
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:  -4.706
MDCK Permeability:  4.484645978664048e-05
Pgp-inhibitor:  0.041
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.166
Plasma Protein Binding (PPB):  94.72539520263672%
Volume Distribution (VD):  0.533
Pgp-substrate:  4.306063652038574%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.347
CYP2C19-inhibitor:  0.977
CYP2C19-substrate:  0.104
CYP2C9-inhibitor:  0.934
CYP2C9-substrate:  0.887
CYP2D6-inhibitor:  0.929
CYP2D6-substrate:  0.703
CYP3A4-inhibitor:  0.949
CYP3A4-substrate:  0.219

ADMET: Excretion

Clearance (CL):  14.355
Half-life (T1/2):  0.266

ADMET: Toxicity

hERG Blockers:  0.223
Human Hepatotoxicity (H-HT):  0.048
Drug-inuced Liver Injury (DILI):  0.928
AMES Toxicity:  0.346
Rat Oral Acute Toxicity:  0.227
Maximum Recommended Daily Dose:  0.059
Skin Sensitization:  0.063
Carcinogencity:  0.853
Eye Corrosion:  0.004
Eye Irritation:  0.611
Respiratory Toxicity:  0.863

Download Data

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

  Natural Product: NPC132606

Natural Product ID:  NPC132606
Common Name*:   SDJBCBKWKASUCJ-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SDJBCBKWKASUCJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H14O6/c1-22-19-12(3-5-16-13(19)6-7-23-16)15(21)9-14(20)11-2-4-17-18(8-11)25-10-24-17/h2-8H,9-10H2,1H3
SMILES:  COc1c(ccc2c1cco2)C(=O)CC(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   627910
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003475] Retro-dihydrochalcones

*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
NPO18094 Euonymus atropurpureus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18094 Euonymus atropurpureus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6716 Amphimedon paraviridis Species Niphatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17156 Neolitsea zeylanica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18094 Euonymus atropurpureus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17852 Chilo suppressalis Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9416 Ostrea chilensis Species Ostreidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4860 Coccinia grandis Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17384 Festuca versuta Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12255 Jasminum humile Species Oleaceae 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 NPC132606 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 NPC132606 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