Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:35 UTC
Primary IDFDB012327
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOrotic acid
DescriptionOccurs in milk and other biol. systems. Salts used as dietary and mineral supplements Orotic acid is a heterocyclic compound and an acid; it is also known as pyrimidinecarboxylic acid. It was once believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin but is instead manufactured in the body by intestinal flora. Orotic acid is found in milk and milk products.
CAS Number65-86-1
Structure
Thumb
Synonyms
SynonymSource
OrotateGenerator
1,2,3,4-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acidbiospider
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acidHMDB
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acidHMDB
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid, 9CIdb_source
1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeureHMDB
2,6-Dihydroxy-4-pyrimidinecarboxylic acidHMDB
2,6-Dihydroxypyrimidine-4-carboxylic acidbiospider
2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acidbiospider
2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acidbiospider
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acidbiospider
2,6-dioxo-3H-pyrimidine-4-carboxylic acidbiospider
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-biospider
4-Pyrimidinecarboxylic acid, 2,6-dihydroxy-biospider
6-Carboxy-2,4-dihydroxypyrimidinebiospider
6-Carboxyuracilbiospider
6-Uracilcarboxylic acidbiospider
Acide orotiqueHMDB
Acido oroticoHMDB
Acidum oroticumHMDB
Animal galactose factorbiospider
LactiniumHMDB
MolkensaeureHMDB
OROHMDB
Orodinbiospider
Oropurbiospider
Orotic acid, BAN, INNdb_source
Orotoninbiospider
Orotonsanbiospider
OrotsaeureChEBI
OrotsaureHMDB
Oroturicbiospider
Orotylbiospider
Pyrimidinecarboxylic acidmanual
Uracil-6-carbosaeureHMDB
Uracil-6-carboxylatebiospider
Uracil-6-carboxylic aciddb_source
Vitamin B13db_source
Whey factordb_source
Predicted Properties
PropertyValueSource
Water Solubility12.8 g/LALOGPS
logP0.52ALOGPS
logP0.76ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)0.34ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.83 m³·mol⁻¹ChemAxon
Polarizability12.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H8N4O8
IUPAC namebis(2,6-dihydroxypyrimidine-4-carboxylic acid)
InChI IdentifierInChI=1S/2C5H4N2O4/c2*8-3-1-2(4(9)10)6-5(11)7-3/h2*1H,(H,9,10)(H2,6,7,8,11)
InChI KeyHTXAWQWIIRILGC-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC(=O)NC(=O)N1.OC(=O)C1=NC(O)=NC(O)=C1
Average Molecular Weight312.1925
Monoisotopic Molecular Weight312.034213252
Classification
Description Belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidinecarboxylic acids
Alternative Parents
Substituents
  • Hydropyrimidine carboxylic acid derivative
  • Pyrimidine-6-carboxylic acid
  • Pyrimidone
  • Hydropyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Urea
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 38.47%; H 2.58%; N 17.95%; O 41.00%DFC
Melting PointMp 345-346°DFC
Boiling PointNot Available
Experimental Water Solubility1.82 mg/mL at 18 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-0.83SANGSTER (1994)
Experimental pKapKa2 9.55 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID942
ChEMBL IDCHEMBL1235017
KEGG Compound IDC00295
Pubchem Compound ID967
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02262
HMDB IDHMDB00226
CRC / DFC (Dictionary of Food Compounds) IDHGJ17-P:HGJ17-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34527
KNApSAcK IDC00019689
HET IDORO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOrotic_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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference