Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2018-05-29 00:57:26 UTC
Primary IDFDB012321
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOrotidylic acid
DescriptionFormed in the biosynthetic pathway in yeast Orotidine 5'-monophosphate (OMP), also known as orotidylic acid, is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate.; Orotidylic acid (OMP), is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. Decarboxylation by Orotidylate decarboxylase affords Uridine 5'-phosphate which is the route to Uridine and its derivatives de novo and consequently one of the most important processes in nucleic acid synthesis (Dictionary of Organic Compounds). In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result.
CAS Number2149-82-8
Structure
Thumb
Synonyms
SynonymSource
1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-ONO-b-D-ribofuranosyl)-4-pyrimidinecarboxylateHMDB
1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-ONO-b-D-ribofuranosyl)-4-pyrimidinecarboxylic acidHMDB
1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-ONO-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylateHMDB
1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-ONO-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylic acidHMDB
2,6-dioxo-3-(5-O-ONO-beta-D-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acidHMDB
2,6-dioxo-3-(5-O-ONO-beta-delta-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acidHMDB
5-(Dihydrogen ate)orotidineHMDB
5-(Dihydrogen phosphate)orotidinebiospider
5'-(Dihydrogen ate) 6-carboxy-uridineHMDB
5'-(Dihydrogen ate) orotidineHMDB
5'-(dihydrogen phosphate) 6-carboxy-uridinebiospider
5'-(dihydrogen phosphate) Orotidinebiospider
5'-ate OrotidineHMDB
5'-OMPbiospider
5'-phosphate Orotidinebiospider
6-carboxy-5'-uridylatebiospider
6-carboxy-5'-uridylic acidbiospider
Ometoprimbiospider
OMPdb_source
Omp (nucleotide)biospider
Orotidine 5'-(dihydrogen ate)ChEBI
Orotidine 5'-(dihydrogen ic acid)Generator
Orotidine 5'-(dihydrogen phosphate), 8CIdb_source
Orotidine 5'-ateChEBI
Orotidine 5'-ic acidGenerator
Orotidine 5'-monoateHMDB
Orotidine 5'-monophosphatebiospider
Orotidine monoateHMDB
Orotidine monophosphatebiospider
Orotidine-5'-ateHMDB
OROTIDINE-5'-MONOPHOSPHATEbiospider
orotidine-5'-phosphatebiospider
Orotidine, 5'-(dihydrogen phosphate) (8CI)biospider
Orotidine, 5'-phosphate (6CI,7CI)biospider
Orotidylatebiospider
Orotidylic aciddb_source
uridine, 6-carboxy-, 5'-(dihydrogen phosphate)biospider
Predicted Properties
PropertyValueSource
Water Solubility9.39 g/LALOGPS
logP-1.7ALOGPS
logP-2.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.65 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.07 m³·mol⁻¹ChemAxon
Polarizability29.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H13N2O11P
IUPAC name3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid
InChI IdentifierInChI=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)
InChI KeyKYOBSHFOBAOFBF-UHFFFAOYSA-N
Isomeric SMILESOC1C(COP(O)(O)=O)OC(C1O)N1C(=O)N=C(O)C=C1C(O)=O
Average Molecular Weight368.1908
Monoisotopic Molecular Weight368.02569578
Classification
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine 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
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Urea
  • Lactam
  • 1,2-diol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • 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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 32.62%; H 3.56%; N 7.61%; O 47.80%; P 8.41%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0913000000-784a672d2b2ebdfb7851JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1911000000-59808dfcdd4e4454362eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-cd1f023f810fb88c433fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zor-5905000000-136688d556d7ce120ae6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9601000000-f3f3a60a64136e890abcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9500000000-48d1a77c2c8afcfa53d5JSpectraViewer
ChemSpider ID141140
ChEMBL IDCHEMBL1207358
KEGG Compound IDC01103
Pubchem Compound ID160617
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02957
HMDB IDHMDB00218
CRC / DFC (Dictionary of Food Compounds) IDHCZ97-N:HGH68-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36813
KNApSAcK IDNot Available
HET IDOMP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOrotidylic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Uridine 5'-monophosphate synthaseUMPSP11172
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046 map00240
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference