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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 19:12:38 UTC
Update Date2021-09-14 15:45:29 UTC
HMDB IDHMDB0003349
Secondary Accession Numbers
  • HMDB03349
Metabolite Identification
Common 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. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. L-Dihydroorotic acid is a drug. 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; which is catalyzed by 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 the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, L-dihydroorotic acid has been detected, but not quantified in several different foods, such as black chokeberries, vanilla, sweet basils, soy beans, and broad beans.
Structure
Data?1582752272
Synonyms
ValueSource
(S)-4,5-Dihydroorotic acidChEBI
Dihydro-L-orotic acidChEBI
(S)-4,5-DihydroorotateKegg
L-DihydroorotateKegg
Dihydro-L-orotateGenerator
(S)-DihydroorotateHMDB
4,5-Dihydroorotic acid, (L)-isomerHMDB
5,6-DihydroorotateHMDB
4,5-Dihydroorotic acidHMDB
4,5-Dihydroorotic acid, (DL)-isomerHMDB
DihydroorotateHMDB
Hydroorotic acidHMDB
4,5-Dihydroorotic acid, (D)-isomerHMDB
Chemical FormulaC5H6N2O4
Average Molecular Weight158.1121
Monoisotopic Molecular Weight158.03275669
IUPAC Name(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional NameL-dihydroorotic acid
CAS Registry Number5988-19-2
SMILES
OC(=O)[C@@H]1CC(=O)NC(=O)N1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalAstarita_neg123.030932474
AllCCS[M-H]-ExperimentalNot Available132.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00001767
DarkChem[M+H]+PredictedNot Available136.26131661259
DarkChem[M-H]-PredictedNot Available127.99331661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
L-Dihydroorotic acid,1TMS,#11639.5826https://arxiv.org/abs/1905.12712
L-Dihydroorotic acid,1TMS,#21677.1279https://arxiv.org/abs/1905.12712
L-Dihydroorotic acid,1TMS,#31654.6171https://arxiv.org/abs/1905.12712
L-Dihydroorotic acid,1TBDMS,#11894.0219https://arxiv.org/abs/1905.12712
L-Dihydroorotic acid,1TBDMS,#21969.2877https://arxiv.org/abs/1905.12712
L-Dihydroorotic acid,1TBDMS,#31951.0737https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfs-1920000000-6e853bcb65fafce1f25e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000j-1900000000-4c364adc386eb5db027b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfs-0930000000-373786ac89c19f0cbc6b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0pb9-2951000000-9975cf569acb6854865d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-005a-5938000000-6f622577780cd53385eb2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfs-1920000000-6e853bcb65fafce1f25e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0pb9-2951000000-9975cf569acb6854865d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005a-5938000000-6f622577780cd53385eb2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-248b8d6d703ba73c20582016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3900000000-b0776f22820e6e570a092017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-059i-9700000000-681989bb70419ccf0e262012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-c08746cfe4c476aff9422012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-c59db6f9b23380c30e8c2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-2920000000-1c8b06ed77517a0e86062017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03k9-4900000000-5b6e94f06ce0c97ad7512017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9800000000-933d1487bcb4d23e2a5a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-34d46a3aa973f0412a452021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-0004fe5f5bbd6b1f1a412021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9000000000-9accaaec3ae3b41f55a92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-41686c36ddb271856b652021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-074u-9500000000-c4e4ed6470c8ad78afec2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8214c2f0d9df1ac7c79c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-022i-9400000000-257f9838bad9d558822c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2e8bea71938b0c3ee5482021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-8cda59dcc275524136f42021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2ddb498acc970a567f6b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-5900000000-4b73ae512e57466dd4e62016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-d6c31a36d6fe5c68d9e12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-c84801951eaa1da750f72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-4ae1d11ab20f903606c32016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-aec3a40befb20e60f21b2016-09-12View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2016-09-22View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)2016-09-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02129
Phenol Explorer Compound IDNot Available
FooDB IDFDB023149
KNApSAcK IDC00007302
Chemspider ID388355
KEGG Compound IDC00337
BioCyc IDDI-H-OROTATE
BiGG ID34662
Wikipedia Link4,5-Dihydroorotic acid
METLIN ID6899
PubChem Compound439216
PDB IDNot Available
ChEBI ID17025
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
DHODH
Uniprot ID:
Q02127
Molecular weight:
42866.93
Reactions
L-Dihydroorotic acid + a quinone → Orotic acid + a quinoldetails
L-Dihydroorotic acid + Quinone → Orotic acid + Hydroquinonedetails
General function:
Involved in hydrolase activity
Specific function:
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:
CAD
Uniprot ID:
P27708
Molecular weight:
242981.73
Reactions
L-Dihydroorotic acid + Water → Ureidosuccinic aciddetails