Human Metabolome Database Version 3.5

Showing metabocard for 4,5-Dihydroorotic acid (HMDB00528)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:46 -0700
Secondary Accession Numbers
  • HMDB11746
Metabolite Identification
Common Name 4,5-Dihydroorotic acid
Description 4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC], which is part of the pyrimidine metabolism pathway. (KEGG) Dihydroorotate is oxidized by Dihydroorotate dehydrogenases (DHODs) to orotate. These dehydrogenases use their FMN (flavin mononucleotide) prosthetic group to abstract a hydride equivalent from C6 to deprotonate C5.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  1. (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  2. (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  3. (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  4. (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  5. (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
  6. (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
  7. 2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate
  8. 2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid
  9. 4,5-Dihydroorotate
  10. 4,5-Dihydroorotic acid
  11. 5,6-Dihydroorotate
  12. L-Hydroorotate
  13. L-Hydroorotic acid
  14. R,S-Hydroorotate
Chemical Formula C5H6N2O4
Average Molecular Weight 158.1121
Monoisotopic Molecular Weight 158.03275669
IUPAC Name 2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional IUPAC Name dihydroorotic acid
CAS Registry Number 155-54-4
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)
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Diazines
Sub Class Pyrimidines and Pyrimidine Derivatives
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Pyrimidines and Pyrimidine Derivatives
  • Ureides
  • dihydroorotic acid(ChEBI)
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Acid Imide, N Unsubstituted
  • Urea
Direct Parent Pyrimidones
Status Expected and Not Quantified
  • Endogenous
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 12.7 g/L ALOGPS
LogP -1.70 ALOGPS
LogP -1.5 ChemAxon
LogS -1.10 ALOGPS
pKa (strongest acidic) 3.28 ChemAxon
pKa (strongest basic) -8.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 95.5 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 31.58 ChemAxon
Polarizability 13.05 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations Not Available
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022096
KNApSAcK ID Not Available
Chemspider ID 628 Link_out
KEGG Compound ID C00337 Link_out
BioCyc ID DI-H-OROTATE Link_out
BiGG ID Not Available
Wikipedia Link 4,5-Dihydroorotic acid Link_out
NuGOwiki Link HMDB00528 Link_out
Metagene Link HMDB00528 Link_out
METLIN ID 5513 Link_out
PubChem Compound 648 Link_out
PDB ID Not Available
ChEBI ID 30865 Link_out
Synthesis Reference Burger, Klaus; Neuhauser, Horst; Rudolph, Martin. A new, preparatively simple way to dihydroorotic acid, 1-methyl-4,5-dihydroorotic acid and their derivatives. Chemiker-Zeitung (1990), 114(7-8), 251-5.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out

Name: Dihydroorotate dehydrogenase (quinone), mitochondrial
Reactions: Not Available
Gene Name: DHODH
Uniprot ID: Q02127 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: CAD protein
Reactions: Not Available
Gene Name: CAD
Uniprot ID: P27708 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA