Showing Compound 3-Indole carboxylic acid glucuronide (FDB029324)

Record Information

Version

1.0

Creation date

2011-09-21 01:54:00 UTC

Update date

2017-04-03 04:56:45 UTC

Primary ID

FDB029324

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Indole carboxylic acid glucuronide

Description

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. [HMDB]

CAS Number

120-72-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
3-Indole Carboxylic acid glucuronide	hmdb
Indole - 3 Carboxylate glucuronide	hmdb

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

Chemical Formula

C15H15NO8

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

337.2815

Monoisotopic Molecular Weight

337.079766461

Classification

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 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Organ and components:

Role

Biological role:

Waste product

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3-Indole carboxylic acid glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9221000000-e405acbb88ebd4f37923	Spectrum
Predicted GC-MS	3-Indole carboxylic acid glucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-4941047000-f01e76abc2e863b6a421	Spectrum
Predicted GC-MS	3-Indole carboxylic acid glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0902000000-e8fb84e81fcefb88928b	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-c6aa02214865ae939df3	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-1900000000-7c819f04717299b3f743	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03y3-1913000000-4ae8bab45fad6c393e9f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-1900000000-18e5eb04fe891824393f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03xu-5900000000-af080777a9b1c93909a7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0609000000-9768d5748961306bdf08	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-0902000000-fe9a3cf27ec94e3aaf83	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-1900000000-15a5ec877ba7065f42c6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0509000000-642d74c686a5391c7534	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-2932000000-0fefa625351cecfa36e0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1900000000-088ab2e521f234147fe4	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

28533205

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53481645

Pubchem Substance ID

Not Available

ChEBI ID

68486

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB13189

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mothball	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
burnt	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference