(S)-dihydroorotate (PAMDB110145)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110145
Identification
Name: (S)-dihydroorotate
Description:A dihydroorotate that is the conjugate base of (S)-dihydroorotic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • dihydro-L-orotate
  • (S)-4,5-dihydroorotate
  • (S)-4,5-dihydroorotic acid
  • (S)-hydroorotic acid
  • (S)-di-H-orotate
  • L-dihydroorotate
  • 4,5-dihydro-L-orotate
  • L-4,5-dihydroorotate
  • (S)-4-pyrimidinecarboxylic acid
Chemical Formula: C5H5N2O4
Average Molecular Weight: 157.1
Monoisotopic Molecular Weight: 158.0327566914
InChI Key: UFIVEPVSAGBUSI-REOHCLBHSA-M
InChI: 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)/p-1/t2-/m0/s1
CAS number: 155-54-4
IUPAC Name:(4S)-2,6-dioxohexahydropyrimidine-4-carboxylate
Traditional IUPAC Name: dihydroorotic acid
SMILES:C1(C(=O)NC(=O)NC(C(=O)[O-])1)
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha 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
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
  • monocarboxylic acid anion (CHEBI:30867)
  • a small molecule (DI-H-OROTATE)
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Ubiquinones + (S)-dihydroorotate → Ubiquinols + orotate
(S)-dihydroorotate + NAD+ → Hydrogen ion + orotate + NADH
Pathways:
  • superpathway of pyrimidine ribonucleotides de novo biosynthesisPWY0-162
  • superpathway of histidine, purine, and pyrimidine biosynthesisPRPP-PWY
  • UMP biosynthesisPWY-5686
  • superpathway of pyrimidine deoxyribonucleotides de novo biosynthesisPWY-7211
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-c8ce0433c02db41880b9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-56601203ef19b09212feView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-b6342346ce51dd871eaaView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
    1D NMR1H NMR SpectrumNot Available
    2D NMR[1H,13C] 2D NMR SpectrumNot Available
    References
    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. [19212411 ]
    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
    External Links:
    ResourceLink
    CAS155-54-4
    CAS5988-19-2
    ChEBI30864
    ChemSpider4573876
    HMDBHMDB00528
    IAF126034662
    KEGGC00337
    MetaboLightsMTBLC30864
    PubChem5460289