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Showing Compound orotate (FDB031072)

Record Information
Version1.0
Creation date2015-05-07 20:57:19 UTC
Update date2025-11-19 03:02:57 UTC
Primary IDFDB031072
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameorotate
DescriptionOrotic acid, also known as orotate or orotsaeure, 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. Orotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Orotic acid exists in all living species, ranging from bacteria to humans. Within humans, orotic acid participates in a number of enzymatic reactions. In particular, orotic acid can be biosynthesized from L-dihydroorotic acid and quinone through its interaction with the enzyme dihydroorotate dehydrogenase (quinone), mitochondrial. In addition, orotic acid and phosphoribosyl pyrophosphate can be converted into orotidylic acid; which is catalyzed by the enzyme uridine monophosphate synthetase isoform a. In humans, orotic acid is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Orotic acid is found, on average, in the highest concentration within milk (cow). Orotic acid has also been detected, but not quantified in, several different foods, such as okra, passion fruits, strawberry guava, cupuaçus, and mango. This could make orotic acid a potential biomarker for the consumption of these foods. Orotic acid is a potentially toxic compound. Orotic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, canavan disease, and phosphoenolpyruvate carboxykinase deficiency 1, cytosolic; orotic acid has also been linked to several inborn metabolic disorders including n-acetylglutamate synthetase deficiency and ornithine transcarbamylase deficiency. A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.
CAS Number65-86-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
OrotsaeureChEBI
Uracil-6-carboxylic acidChEBI
Uracil-6-carboxylateGenerator
OrotateGenerator
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-dioxopyrimidin-4-carbonsaeureHMDB
2,6-Dihydroxy-4-pyrimidinecarboxylic acidHMDB
2,6-Dihydroxypyrimidine-4-carboxylic acidHMDB
2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acidHMDB
2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acidHMDB
6-Carboxy-2,4-dihydroxypyrimidineHMDB
6-CarboxyuracilHMDB
6-Uracilcarboxylic acidHMDB
Acide orotiqueHMDB
Acido oroticoHMDB
Acidum oroticumHMDB
Animal galactose factorHMDB
LactiniumHMDB
MolkensaeureHMDB
OROHMDB
OrodinHMDB
OropurHMDB
OrotoninHMDB
OrotonsanHMDB
OrotsaureHMDB
OroturicHMDB
OrotylHMDB
Uracil-6-carbosaeureHMDB
Vitamin b13HMDB
Whey factorHMDB
Zinc orotateHMDB
Orotate, zincHMDB
Acid, oroticHMDB
Orotate, potassiumHMDB
Potassium orotateHMDB
Orotate, sodiumHMDB
Sodium orotateHMDB
Predicted Properties
PropertyValueSource
Water Solubility4.51 g/LALOGPS
logP-0.89ALOGPS
logP-1.2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.27 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H4N2O4
IUPAC name2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
InChI IdentifierInChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
InChI KeyPXQPEWDEAKTCGB-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC(=O)NC(=O)N1
Average Molecular Weight156.0963
Monoisotopic Molecular Weight156.017106626
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
  • Pyrimidine-6-carboxylic acid
  • Hydropyrimidine carboxylic acid derivative
  • Pyrimidone
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Lactam
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-066r-9300000000-e5c3ef3304f93a38628c2014-09-20View Spectrum
GC-MSorotate, non-derivatized, GC-MS Spectrumsplash10-0udi-1982000000-b20f2ec9a2f1acc84ae1Spectrum
GC-MSorotate, 3 TMS, GC-MS Spectrumsplash10-0zfr-2693000000-07bf11b5177412647d9bSpectrum
GC-MSorotate, non-derivatized, GC-MS Spectrumsplash10-0udi-1982000000-b20f2ec9a2f1acc84ae1Spectrum
GC-MSorotate, non-derivatized, GC-MS Spectrumsplash10-0zfr-2693000000-07bf11b5177412647d9bSpectrum
GC-MSorotate, non-derivatized, GC-MS Spectrumsplash10-0udi-1972000000-c04fb7381d3ca07c9b0aSpectrum
Predicted GC-MSorotate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06ri-6900000000-4ba5fde1f8f62c4a2ba2Spectrum
Predicted GC-MSorotate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0229-9850000000-8164142820eb5162e753Spectrum
Predicted GC-MSorotate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSorotate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSorotate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSorotate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSorotate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSorotate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-0900000000-81d73aed73c250fff3ae2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9300000000-ecb08d1854a2789480d12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9100000000-15748a4c13636c42f4f92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-02ti-4900000000-6fd6312d81f94faaaf112012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-1b7abf52e4a01cb855412012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-1b7abf52e4a01cb855412017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-3dff3caa5c10aff8ce462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-02ti-4900000000-6fd6312d81f94faaaf112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-351f585d58b38f6132de2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-4e46209ca236b470bf7f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-9300000000-aa9cd31d715d134ee8dd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-cdd01e740b6f9d1a909a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-baf39ad8ab6f08fb1a7b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-0900000000-1ad59feda583f2247b212015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-0d0d27215e9f39a2a15b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-918a38777f5d4e0496972015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a832015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-7900000000-303fe3e06e98f518a2ee2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b2c02975bbba65c2f1c62015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-0900000000-1ad59feda583f2247b212015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-0d0d27215e9f39a2a15b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-918a38777f5d4e0496972015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a832015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-7900000000-303fe3e06e98f518a2ee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b2c02975bbba65c2f1c62015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID942
ChEMBL IDCHEMBL1235017
KEGG Compound IDC00295
Pubchem Compound ID967
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0000226
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00019689
HET IDNot Available
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
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of Orotic acidSMP0124870 Not Available
Metabolism and Physiological Effects of UridineSMP0124871 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference