FComEx: L-Dihydroorotic acid (PC000776)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:38 UTC

Update date

2017-01-19 02:36:36 UTC

FoodComEx ID

PC000776

FoodDB Record

FDB023149

Chemical Information

Name

L-Dihydroorotic acid

Description

L-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Dihydroorotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The (S)-enantiomer of dihydroorotic acid that is an intermediate in the metabolism of pyridine. L-Dihydroorotic acid exists in all living species, ranging from bacteria to humans. Within humans, L-dihydroorotic acid participates in a number of enzymatic reactions. In particular, L-dihydroorotic acid can be biosynthesized from ureidosuccinic acid through the action of the enzyme cad protein. In addition, L-dihydroorotic acid and quinone can be converted into orotic acid through the action of the enzyme dihydroorotate dehydrogenase (quinone), mitochondrial. In humans, L-dihydroorotic acid is involved in pyrimidine metabolism. Outside of the human body, L-Dihydroorotic acid has been detected, but not quantified in, several different foods, such as american pokeweeds, prunus (cherry, plum), red huckleberries, white lupines, and shallots. This could make L-dihydroorotic acid a potential biomarker for the consumption of these foods.

CAS Number

5988-19-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S)-4,5-Dihydroorotate	hmdb
(S)-Dihydroorotate	hmdb
Dihydro-L-orotate	hmdb
Dihydro-L-orotic acid	hmdb
L-Dihydroorotate	hmdb
L-Dihydroorotic acid	hmdb

Chemical Formula

C5H6N2O4

IUPAC name

(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid

InChI Identifier

InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1

InChI Key

UFIVEPVSAGBUSI-REOHCLBHSA-N

Isomeric SMILES

OC(=O)[C@@H]1CC(=O)NC(=O)N1

Average Molecular Weight

158.1121

Monoisotopic Molecular Weight

158.03275669

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents