| Common Name |
4,5-Dihydroorotic acid
| Description |
4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC 1.3.1.14], 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
5,6-dihydro-Orotic acidChEBI
DL-Dihydroortotic acidChEBI
Hydroorotic acidChEBI
5,6-dihydro-OrotateGenerator
4,5-DihydroorotateGenerator
DL-DihydroortotateGenerator
HydroorotateGenerator
(+)-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-DihydroorotateMeSH
4,5-Dihydroorotic acid, (L)-isomerMeSH
DihydroorotateMeSH
4,5-Dihydroorotic acid, (D)-isomerMeSH
4,5-Dihydroorotic acid, (DL)-isomerMeSH
| Chemical Formlia |
C5H6N2O4
| Average Molecliar Weight |
158.1121
| Monoisotopic Molecliar Weight |
158.03275669
| IUPAC Name |
2,6-dioxo-1,3-diazinane-4-carboxylic acid
| Traditional Name |
dihydroorotic acid
| CAS Registry Number |
155-54-4
| 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 Key |
UFIVEPVSAGBUSI-UHFFFAOYSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility12.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m3·mol-1ChemAxon
Polarizability13.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-c8ce0433c02db41880b9View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-56601203ef19b09212feView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-b6342346ce51dd871eaaView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar 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
| External Links |
| 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
| KEGG Compound ID |
C00337
| BioCyc ID |
DI-H-OROTATE
| BiGG ID |
Not Available
| Wikipedia Link |
4,5-Dihydroorotic acid
| NuGOwiki Link |
HMDB00528
| Metagene Link |
HMDB00528
| METLIN ID |
5513
| PubChem Compound |
648
| PDB ID |
Not Available
| ChEBI ID |
30865
Product: Asarylaldehyde
References |
| 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 |
- 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
PMID: 23376397