Structure

This browser does not support HTML5/Canvas.

Physi-Chem Properties

Molecular Weight:  342.1
Volume:  316.813
LogP:  -0.555
LogD:  -0.532
LogS:  -1.904
# Rotatable Bonds:  5
TPSA:  156.91
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.357
Synthetic Accessibility Score:  3.644
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.942
MDCK Permeability:  1.9642755432869308e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.835
Human Intestinal Absorption (HIA):  0.741
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.221
Plasma Protein Binding (PPB):  69.1373519897461%
Volume Distribution (VD):  0.274
Pgp-substrate:  26.734235763549805%

ADMET: Metabolism

CYP1A2-inhibitor:  0.177
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.179
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.137
CYP3A4-inhibitor:  0.025
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.613
Half-life (T1/2):  0.874

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.119
Drug-inuced Liver Injury (DILI):  0.88
AMES Toxicity:  0.207
Rat Oral Acute Toxicity:  0.054
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.341
Carcinogencity:  0.11
Eye Corrosion:  0.005
Eye Irritation:  0.207
Respiratory Toxicity:  0.03

Download Data

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

  Natural Product: NPC186418

Natural Product ID:  NPC186418
Common Name*:   Caffeic Acid 4-O-Glucoside
IUPAC Name:   (E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
Synonyms:  
Standard InCHIKey:  OHEYCHKLBCPRLZ-VHCZEJTMSA-N
Standard InCHI:  InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-3-1-7(5-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2ccc(cc2O)/C=C/C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3092675
PubChem CID:   14825516
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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

☑ 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

☑ 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

☑ 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 NPC186418 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

  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 NPC186418 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

  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