FComEx: 1,3,7-Trimethyluric acid (PC000832)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:58 UTC

Update date

2017-01-19 02:36:38 UTC

FoodComEx ID

PC000832

FoodDB Record

FDB022854

Chemical Information

Name

1,3,7-Trimethyluric acid

Description

1,3,7-Trimethyluric acid, also known as 8-oxy-caffeine or 1,3,7-trimethylate, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 1,3,7-Trimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,3,7-Trimethyluric acid exists in all living organisms, ranging from bacteria to humans. 1,3,7-trimethyluric acid can be biosynthesized from caffeine; which is catalyzed by the enzymes cytochrome P450 1A2, cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C9, and cytochrome P450 2E1. In humans, 1,3,7-trimethyluric acid is involved in caffeine metabolism. Outside of the human body, 1,3,7-Trimethyluric acid has been detected, but not quantified in, several different foods, such as rubus (blackberry, raspberry), passion fruits, mountain yams, wasabis, and pigeon pea. This could make 1,3,7-trimethyluric acid a potential biomarker for the consumption of these foods. An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8, and the nitrogens at positions 1, 3, and 7 are substituted by methyl groups.

CAS Number

5415-44-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3, 7-Trimethyluric acid	hmdb
1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione	hmdb
1,3,7-Trimethylate	Generator
1,3,7-Trimethylic acid	Generator
1,3,7-Trimethylurate	ChEBI
2,6,8-Trihydroxy-1,3,7-trimethylpurine	hmdb
7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trione	hmdb
8-hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione	hmdb
8-oxy-caffeine	hmdb
Trimethyl uric acid	hmdb

Chemical Formula

C8H10N4O3

IUPAC name

1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

InChI Identifier

InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)

InChI Key

BYXCFUMGEBZDDI-UHFFFAOYSA-N

Isomeric SMILES

CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C

Average Molecular Weight

210.19

Monoisotopic Molecular Weight

210.075290206

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents