Showing Compound 5-Hydroxy-6-methoxyindole glucuronide (FDB027515)

Record Information

Version

1.0

Creation date

2011-09-21 01:25:45 UTC

Update date

2015-07-21 06:59:08 UTC

Primary ID

FDB027515

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-Hydroxy-6-methoxyindole glucuronide

Description

5-Hydroxy-6-methoxyindole glucuronide is a natural human metabolite of 5-hydroxy-6-methoxyindole generated in the liver by UDP glucuonyltransferase. 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

77463-71-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(6-methoxy-1H-indol-5-yl)oxy]oxane-2-carboxylate	Generator, HMDB
5-H-6-MIG	MeSH, HMDB
5-Hydroxy-6-methoxyindole glucuronide	MeSH
5-Hydroxy-6-methoxyindole glucuronoside	HMDB
5-hydroxy-6-methoxyindole glucuronoside	hmdb
6-Methoxy-1H-indol-5-yl-beta-D-glucopyranosiduronic acid	HMDB
6-methoxy-1H-indol-5-yl-beta-D-Glucopyranosiduronic acid	hmdb
6-Methoxy-1H-indol-5-yl-beta-delta-glucopyranosiduronic acid	HMDB
6-methoxy-1H-indol-5-yl-beta-delta-Glucopyranosiduronic acid	hmdb

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-0.15	ALOGPS
logP	-0.34	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.6 m³·mol⁻¹	ChemAxon
Polarizability	32.12 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

C15H17NO8

IUPAC name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-methoxy-1H-indol-5-yl)oxy]oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C15H17NO8/c1-22-8-5-7-6(2-3-16-7)4-9(8)23-15-12(19)10(17)11(18)13(24-15)14(20)21/h2-5,10-13,15-19H,1H3,(H,20,21)/t10-,11-,12+,13-,15+/m0/s1

InChI Key

MLRMPLSCFCMXGJ-DKBOKBLXSA-N

Isomeric SMILES

COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C2C=CNC2=C1

Average Molecular Weight

339.2974

Monoisotopic Molecular Weight

339.095416525

Classification

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Pyrrole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Ether
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Organ and components:

Role

Biological role:

Waste product

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	5-Hydroxy-6-methoxyindole glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0abc-9242000000-dfd4e387e92fad5d8ca5	Spectrum
Predicted GC-MS	5-Hydroxy-6-methoxyindole glucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dr-6272049000-92b416fd6dd27728ee22	Spectrum
Predicted GC-MS	5-Hydroxy-6-methoxyindole 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-0905000000-ca082ed83a5b427342ab	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-0aafd68dcafe7432d76c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0292-1900000000-484677b40c4cabf2d597	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01pc-2937000000-04ac3e501bd631f2a913	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-1911000000-27b6a6ec8276878fbb00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dj-2900000000-81b42186c92d3205d920	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0209000000-f617d00b88fec92bf709	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-cad3cfb24cfb543cf152	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2900000000-9404f141e82f935c84aa	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0917000000-b5f6c20ec89ca06e0e2b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0920000000-b39bc3ed964caf8b8041	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3920000000-0f328f7f0a70fb08ce30	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

170259

ChEMBL ID

Not Available

KEGG Compound ID

C03033

Pubchem Compound ID

196512

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB10363

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Beta-glucuronidase	GUSB	P08236
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 1-5	UGT1A5	P35504
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656
UDP-glucuronosyltransferase 2A1	UGT2A1	Q9Y4X1
UDP-glucuronosyltransferase 2A3	UGT2A3	Q6UWM9
UDP-glucuronosyltransferase 2B11	UGT2B11	O75310