ChemFOnt: Showing chemical card for 3-Indole carboxylic acid glucuronide (CFc000008237)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:55 UTC

Chemfont ID

CFc000008237

Molecule Identification

Common Name

3-Indole carboxylic acid glucuronide

Definition

3-Indole carboxylic acid glucuronide is a natural human metabolites of Indole-3-carboxylic acid. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite (PMID 4844607 ) and has been found elevated in patients with liver diseases (PMID 13905029 ). Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Indole carboxylate glucuronide	Generator
Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylic acid glucuronide	HMDB
3-Indole carboxylic acid glucuronoside	HMDB
3-Indolecarboxylate glucuronide	HMDB
3-Indolecarboxylic acid glucuronide	HMDB
3-Indoleformate glucuronide	HMDB
3-Indoleformic acid glucuronide	HMDB
3-Indolylcarboxylate glucuronide	HMDB
3-Indolylcarboxylic acid glucuronide	HMDB
Indole-3 carboxylate glucuronide	HMDB
Indole-3-carboxilic acid-O-glucuronide	HMDB
Indole-3-carboxylic acid glucuronide	HMDB
Indole-3-carboxylic acid glucuronoside	HMDB
Indole-3-carboxylicacid glucuronide	HMDB
(3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylate	Generator

Chemical Formula

C₁₅H₁₅NO₈

Average Molecular Weight

337.2815

Monoisotopic Molecular Weight

337.079766461

IUPAC Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

Traditional Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

CAS Registry Number

120-72-9

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1

InChI Key

BDNWJTRKUBXAGH-DOVARBIBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Indolecarboxylic acid derivative
Indole
Indole or derivatives
Pyrrole-3-carboxylic acid or derivatives
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Oxane
Pyran
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Azacycle
Carboxylic acid
Acetal
Oxacycle
Organic nitrogen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glucosiduronic acid (CHEBI:68486 )
O-acyl carbohydrate (CHEBI:68486 )
indolyl carbohydrate (CHEBI:68486 )

Functional Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013189)

Organ

Liver (HMDB: HMDB0013189)
Kidney (HMDB: HMDB0013189)

Excreta

Biofluid or Excreta

Urine (PMID: 22827565)

Source

Endogenous

Endogenous (HMDB: HMDB0013189)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0013189)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.93 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.018	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	32.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013189

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029324

KNApSAcK ID

Not Available

Chemspider ID

28533205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481645

PDB ID

Not Available

ChEBI ID

68486

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Indole carboxylic acid glucuronide (CFc000008237)

MOL for CFc000008237 (3-Indole carboxylic acid glucuronide)

3D MOL for CFc000008237 (3-Indole carboxylic acid glucuronide)

3D SDF for CFc000008237 (3-Indole carboxylic acid glucuronide)

3D-SDF for CFc000008237 (3-Indole carboxylic acid glucuronide)

PDB for CFc000008237 (3-Indole carboxylic acid glucuronide)

3D PDB for CFc000008237 (3-Indole carboxylic acid glucuronide)

SMILES for CFc000008237 (3-Indole carboxylic acid glucuronide)

INCHI for CFc000008237 (3-Indole carboxylic acid glucuronide)

Structure for CFc000008237 (3-Indole carboxylic acid glucuronide)

3D Structure for CFc000008237 (3-Indole carboxylic acid glucuronide)