Common Name(s)-dihydroorotate
DescriptionL-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. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. L-Dihydroorotic acid is a drug. 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; which is catalyzed by 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 the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, L-dihydroorotic acid has been detected, but not quantified in several different foods, such as black chokeberries, vanilla, sweet basils, soy beans, and broad beans.
Structure
Molecular FormulaC5H6N2O4
Average Mass158.11210
Monoisotopic Mass158.03276
IUPAC Name(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional NameDihydroorotic acid
CAS Registry Number5988-19-2
SMILESO=C1C[C@@H](C(=O)[O-])NC(=O)N1
InChI IdentifierInChI=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 KeyUFIVEPVSAGBUSI-REOHCLBHSA-N
CHEBI IDCHEBI:30864
HMDB IDHMDB0003349
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
UMP Synthase Deficiency (Orotic Aciduria)
StateSolid
Water Solubility1.27e+01 g/l
logP-1.70
logS-1.10
pKa (Strongest Acidic)3.28
pKa (Strongest Basic)-8.19
Hydrogen Acceptor Count4
Hydrogen Donor Count3
Polar Surface Area95.5 Ų
Rotatable Bond Count1
Physiological Charge-1
Formal Charge0
Refractivity31.58 m³·mol⁻¹
Polarizability13.00

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT