Record Information
Version1.0
Creation date2011-09-21 00:25:22 UTC
Update date2024-11-29 22:26:07 UTC
Primary IDFDB023149
Secondary Accession Numbers
  • FDB030169
Chemical Information
FooDB NameL-Dihydroorotic acid
DescriptionL-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, 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. L-Dihydroorotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The (S)-enantiomer of dihydroorotic acid that is an intermediate in the metabolism of pyridine. L-Dihydroorotic acid exists in all living species, ranging from bacteria to humans. Within humans, L-dihydroorotic acid participates in a number of enzymatic reactions. In particular, L-dihydroorotic acid can be biosynthesized from ureidosuccinic acid through the action of the enzyme cad protein. In addition, L-dihydroorotic acid and quinone can be converted into orotic acid through the action of the enzyme dihydroorotate dehydrogenase (quinone), mitochondrial. In humans, L-dihydroorotic acid is involved in pyrimidine metabolism. Outside of the human body, L-Dihydroorotic acid has been detected, but not quantified in, several different foods, such as american pokeweeds, prunus (cherry, plum), red huckleberries, white lupines, and shallots. This could make L-dihydroorotic acid a potential biomarker for the consumption of these foods.
CAS Number5988-19-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m³·mol⁻¹ChemAxon
Polarizability12.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H6N2O4
IUPAC name(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
InChI IdentifierInChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1
InChI KeyUFIVEPVSAGBUSI-REOHCLBHSA-N
Isomeric SMILESOC(=O)[C@@H]1CC(=O)NC(=O)N1
Average Molecular Weight158.1121
Monoisotopic Molecular Weight158.03275669
Classification
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-0zfs-1920000000-6e853bcb65fafce1f25eSpectrum
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-000j-1900000000-4c364adc386eb5db027bSpectrum
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-0zfs-0930000000-373786ac89c19f0cbc6bSpectrum
GC-MSL-Dihydroorotic acid, 3 TMS, GC-MS Spectrumsplash10-0pb9-2951000000-9975cf569acb6854865dSpectrum
GC-MSL-Dihydroorotic acid, 4 TMS, GC-MS Spectrumsplash10-005a-5938000000-6f622577780cd53385ebSpectrum
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-0zfs-1920000000-6e853bcb65fafce1f25eSpectrum
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-0pb9-2951000000-9975cf569acb6854865dSpectrum
GC-MSL-Dihydroorotic acid, non-derivatized, GC-MS Spectrumsplash10-005a-5938000000-6f622577780cd53385ebSpectrum
Predicted GC-MSL-Dihydroorotic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9400000000-248b8d6d703ba73c2058Spectrum
Predicted GC-MSL-Dihydroorotic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3900000000-b0776f22820e6e570a09Spectrum
Predicted GC-MSL-Dihydroorotic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-681989bb70419ccf0e262012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-c08746cfe4c476aff9422012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-c59db6f9b23380c30e8c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-2920000000-1c8b06ed77517a0e86062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03k9-4900000000-5b6e94f06ce0c97ad7512017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9800000000-933d1487bcb4d23e2a5a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-34d46a3aa973f0412a452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-0004fe5f5bbd6b1f1a412021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9000000000-9accaaec3ae3b41f55a92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-41686c36ddb271856b652021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-074u-9500000000-c4e4ed6470c8ad78afec2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8214c2f0d9df1ac7c79c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-022i-9400000000-257f9838bad9d558822c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2e8bea71938b0c3ee5482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-8cda59dcc275524136f42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2ddb498acc970a567f6b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-5900000000-4b73ae512e57466dd4e62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-d6c31a36d6fe5c68d9e12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-c84801951eaa1da750f72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-4ae1d11ab20f903606c32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-aec3a40befb20e60f21b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-b0c5e687f246809cdae92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-6900000000-cb60b796898e6ca4336d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-fccf5d7216b23cffed7a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r6-0900000000-86736ae769db7bc83c232021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, 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, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID439216
Pubchem Substance IDNot Available
ChEBI ID17025
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03349
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference