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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:17 UTC
HMDB IDHMDB0000528
Secondary Accession Numbers
  • HMDB0011746
  • HMDB00528
  • HMDB11746
Metabolite Identification
Common Name4,5-Dihydroorotic acid
Description4,5-Dihydroorotic acid, also known as hydroorotate, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to humans.
Structure
Data?1582752137
Synonyms
ValueSource
5,6-Dihydro-orotic acidChEBI
DL-Dihydroortotic acidChEBI
Hydroorotic acidChEBI
5,6-Dihydro-orotateGenerator
DL-DihydroortotateGenerator
HydroorotateGenerator
4,5-DihydroorotateGenerator
(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
5,6-DihydroorotateHMDB
L-HydroorotateHMDB
L-Hydroorotic acidHMDB
R,S-HydroorotateHMDB
L-DihydroorotateHMDB
4,5-Dihydroorotic acid, (L)-isomerHMDB
DihydroorotateHMDB
4,5-Dihydroorotic acid, (D)-isomerHMDB
4,5-Dihydroorotic acid, (DL)-isomerHMDB
Chemical FormulaC5H6N2O4
Average Molecular Weight158.1121
Monoisotopic Molecular Weight158.03275669
IUPAC Name2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional Namedihydroorotic acid
CAS Registry Number155-54-4
SMILES
OC(=O)C1CC(=O)NC(=O)N1
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)
InChI KeyUFIVEPVSAGBUSI-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • 1,3-diazinane
  • Pyrimidine
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m³·mol⁻¹ChemAxon
Polarizability13.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-248b8d6d703ba73c2058Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3900000000-b0776f22820e6e570a09Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-c8ce0433c02db41880b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-56601203ef19b09212feSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-b6342346ce51dd871eaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2ddb498acc970a567f6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-5900000000-4b73ae512e57466dd4e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-d6c31a36d6fe5c68d9e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-c84801951eaa1da750f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-4ae1d11ab20f903606c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-aec3a40befb20e60f21bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022096
KNApSAcK IDNot Available
Chemspider ID628
KEGG Compound IDC00337
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4,5-Dihydroorotic_acid
METLIN ID5513
PubChem Compound648
PDB IDNot Available
ChEBI ID30865
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceBurger, 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. doi: 10.1038/nature07762. [PubMed:19212411 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
DHODH
Uniprot ID:
Q02127
Molecular weight:
42866.93
General function:
Involved in hydrolase activity
Specific function:
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:
CAD
Uniprot ID:
P27708
Molecular weight:
242981.73