Showing Compound Card for L-Dihydroorotic acid (CDB004954)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:54:08 UTC
Updated at2020-11-18 16:39:06 UTC
CannabisDB IDCDB004954
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. L-Dihydroorotic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight158.11
Monoisotopic Molecular Weight158.0328
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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Dihydroorotate dehydrogenase (quinone), mitochondrialDHODH16q22Q02127 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
CAD proteinCAD2p22-p21P27708 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003349
DrugBank IDDB02129
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dihydroorotate dehydrogenase (quinone), mitochondrial
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