orotidine 5'-phosphate (PAMDB110105)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110105
Identification
Name: orotidine 5'-phosphate
Description:Trianion of orotidine 5'-phosphate arising from deprotonation of carboxylic acid and phosphate functions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • uridine-5\'-phosphate biosynthesis
  • de novo biosynthesis of uridine-5\'-phosphate

  •   de novo biosynthesis of uridine-5\'-monophosphate'
  • WIDTH
  • 500);" onmouseout="return nd();"> UMP biosynthesis :
    orotidine 5'-phosphate + H+ → CO2 + UMP
Chemical Formula: C10H10N2O11P
Average Molecular Weight: 365.17
Monoisotopic Molecular Weight: 368.0256957808
InChI Key: KYOBSHFOBAOFBF-XVFCMESISA-K
InChI: InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/p-3/t4-,6-,7-,8-/m1/s1
CAS number: 2149-82-8
IUPAC Name:2,6-dioxo-3-(5-O-phosphonato-β-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate
Traditional IUPAC Name: 6-carboxy-5'-uridylic acid
SMILES:C(OP(=O)([O-])[O-])C1(OC(C(O)C(O)1)N2(C(C(=O)[O-])=CC(=O)NC(=O)2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct Parent Pyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Pyrimidine-6-carboxylic acid or derivatives
  • Pyrimidine-6-carboxylic acid
  • Hydropyrimidine carboxylic acid derivative
  • Monoalkyl phosphate
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Vinylogous amide
  • Secondary alcohol
  • Urea
  • Lactam
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
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 Solubility8.61 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area203.16 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.74 m3·mol-1ChemAxon
Polarizability29.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0914000000-3337770bad1b3ba8486cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1911000000-f94acf2aa5da3364c517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-5900000000-81a1aba75871162fc05bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0axv-8917000000-d1de3bc4514e88dd288cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9701000000-13540f203bff602cb8f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-2bf7c464e9b79ae5c6a9View in MoNA
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 ]
  • Traut TW: Uridine-5'-phosphate synthase: evidence for substrate cycling involving this bifunctional protein. Arch Biochem Biophys. 1989 Jan;268(1):108-15. [2912371 ]
Synthesis Reference: Ueda, Tohru; Yamamoto, Miyako; Yamane, Akira; Imazawa, Masaoki; Inoue, Hideo. Nucleosides and nucleotides. XXIII. Conversion of uridine nucleotides to the 6-cyano derivatives: synthesis of orotidylic acid. Journal of Carbohydrates, Nucleosides, Nucleotides (1978), 5(3), 261-71.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS2149-82-8
ChEBI57538
HMDBHMDB00218
IAF126036813
KEGGC01103
MetaboLightsMTBLC57538
PubChem25245207