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Showing metabocard for L-Dihydroorotic acid (HMDB0003349)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 19:12:38 UTC
Update Date2022-09-22 18:34:17 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003349 (L-Dihydroorotic acid)


  Mrv1652309042000292D          

 11 11  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
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3D MOL for HMDB0003349 (L-Dihydroorotic acid)

HMDB0003349
     RDKit          3D
L-Dihydroorotic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6098   -0.6879    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -0.3138    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -1.1305    0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -0.0971    0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9006   -0.7090    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1712   -1.8674   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722    0.2145    0.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1530    0.5752   -1.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039    1.4080   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595    2.5124   -1.4661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.9313    0.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340   -1.5668   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -1.8951    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.5551    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115   -0.0350    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    0.5255   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642    1.5805    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  2  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  1
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
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3D SDF for HMDB0003349 (L-Dihydroorotic acid)


  Mrv1652309042000292D          

 11 11  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003349

> <DATABASE_NAME>
hmdb

> <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_KEY>
UFIVEPVSAGBUSI-REOHCLBHSA-N

> <FORMULA>
C5H6N2O4

> <MOLECULAR_WEIGHT>
158.1121

> <EXACT_MASS>
158.03275669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.955416264529363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-1.5232681353333333

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.713668138573995

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2849203199118633

> <JCHEM_PKA_STRONGEST_BASIC>
-8.186843445720307

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
31.575400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-dihydroorotic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003349 (L-Dihydroorotic acid)

HMDB0003349
     RDKit          3D
L-Dihydroorotic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6098   -0.6879    1.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -0.3138    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -1.1305    0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -0.0971    0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9006   -0.7090    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1712   -1.8674   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722    0.2145    0.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1530    0.5752   -1.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039    1.4080   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595    2.5124   -1.4661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.9313    0.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340   -1.5668   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -1.8951    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.5551    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115   -0.0350    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    0.5255   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642    1.5805    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  2  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  1
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
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PDB for HMDB0003349 (L-Dihydroorotic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0003349 (L-Dihydroorotic acid)

COMPND    HMDB0003349
HETATM    1  O1  UNL     1      -2.610  -0.688   1.549  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.744  -0.314   0.710  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.544  -1.130   0.361  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.581  -0.097   0.167  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.901  -0.709   0.108  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.171  -1.867  -0.031  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.972   0.215   0.255  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.153   0.575  -1.076  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.004   1.408  -0.848  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.159   2.512  -1.466  1.00  0.00           O  
HETATM   11  N2  UNL     1      -1.959   0.931   0.085  1.00  0.00           N  
HETATM   12  H1  UNL     1      -0.734  -1.567  -0.664  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.293  -1.895   1.059  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.530   0.555   1.013  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.912  -0.035   0.431  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.593   0.525  -1.978  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.764   1.581   0.323  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   12   13
CONECT    4    5    8   14
CONECT    5    6    6    7
CONECT    7   15
CONECT    8    9   16
CONECT    9   10   10   11
CONECT   11   17
END
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SMILES for HMDB0003349 (L-Dihydroorotic acid)

OC(=O)[C@@H]1CC(=O)NC(=O)N1
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INCHI for HMDB0003349 (L-Dihydroorotic acid)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
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
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg123.030932474
[M-H]-Not Available132.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00001767
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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.26131661259
DarkChem[M-H]-127.99331661259
DeepCCS[M+H]+128.50130932474
DeepCCS[M-H]-125.91830932474
DeepCCS[M-2H]-161.61930932474
DeepCCS[M+Na]+137.030932474
AllCCS[M+H]+134.432859911
AllCCS[M+H-H2O]+130.032859911
AllCCS[M+NH4]+138.632859911
AllCCS[M+Na]+139.732859911
AllCCS[M-H]-126.332859911
AllCCS[M+Na-2H]-127.632859911
AllCCS[M+HCOO]-129.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.35 minutes32390414
Predicted by Siyang on May 30, 20229.796 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.72 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid238.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid821.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid343.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid56.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid202.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid73.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid270.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid277.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)656.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid626.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid70.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid895.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid211.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid261.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate703.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA290.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water339.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-Dihydroorotic acidOC(=O)[C@@H]1CC(=O)NC(=O)N13100.9Standard polar33892256
L-Dihydroorotic acidOC(=O)[C@@H]1CC(=O)NC(=O)N11636.4Standard non polar33892256
L-Dihydroorotic acidOC(=O)[C@@H]1CC(=O)NC(=O)N11846.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Dihydroorotic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N11639.6Semi standard non polar33892256
L-Dihydroorotic acid,1TMS,isomer #2C[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)NC1=O1677.1Semi standard non polar33892256
L-Dihydroorotic acid,1TMS,isomer #3C[Si](C)(C)N1C(=O)NC(=O)C[C@H]1C(=O)O1654.6Semi standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N11693.9Semi standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N11815.5Standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N12895.1Standard polar33892256
L-Dihydroorotic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C1676.2Semi standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C1820.3Standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C3092.7Standard polar33892256
L-Dihydroorotic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)C1=O1640.2Semi standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)C1=O1744.7Standard non polar33892256
L-Dihydroorotic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)C1=O2525.0Standard polar33892256
L-Dihydroorotic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C1672.0Semi standard non polar33892256
L-Dihydroorotic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C1797.3Standard non polar33892256
L-Dihydroorotic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C2213.1Standard polar33892256
L-Dihydroorotic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N11894.0Semi standard non polar33892256
L-Dihydroorotic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)NC1=O1969.3Semi standard non polar33892256
L-Dihydroorotic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C[C@H]1C(=O)O1951.1Semi standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N12153.6Semi standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N12258.8Standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N12839.9Standard polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C2149.1Semi standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C2281.6Standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C3001.0Standard polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2135.0Semi standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2215.5Standard non polar33892256
L-Dihydroorotic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2535.7Standard polar33892256
L-Dihydroorotic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2336.9Semi standard non polar33892256
L-Dihydroorotic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2469.1Standard non polar33892256
L-Dihydroorotic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2459.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfs-1920000000-6e853bcb65fafce1f25e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000j-1900000000-4c364adc386eb5db027b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfs-0930000000-373786ac89c19f0cbc6b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-MS (3 TMS)splash10-0pb9-2951000000-9975cf569acb6854865d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-MS (4 TMS)splash10-005a-5938000000-6f622577780cd53385eb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-EI-TOF (Non-derivatized)splash10-0zfs-1920000000-6e853bcb65fafce1f25e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-MS (Non-derivatized)splash10-0pb9-2951000000-9975cf569acb6854865d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Dihydroorotic acid GC-MS (Non-derivatized)splash10-005a-5938000000-6f622577780cd53385eb2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Dihydroorotic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-248b8d6d703ba73c20582016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Dihydroorotic acid GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3900000000-b0776f22820e6e570a092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Dihydroorotic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-059i-9700000000-681989bb70419ccf0e262012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-9000000000-c08746cfe4c476aff9422012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-006x-9000000000-c59db6f9b23380c30e8c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid , negative-QTOFsplash10-001i-2920000000-1c8b06ed77517a0e86062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid , positive-QTOFsplash10-03k9-4900000000-5b6e94f06ce0c97ad7512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Negative-QTOFsplash10-03dl-9800000000-933d1487bcb4d23e2a5a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 35V, Negative-QTOFsplash10-0006-9000000000-34d46a3aa973f0412a452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Positive-QTOFsplash10-00di-9100000000-0004fe5f5bbd6b1f1a412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Positive-QTOFsplash10-05fr-9000000000-9accaaec3ae3b41f55a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Positive-QTOFsplash10-00di-9000000000-41686c36ddb271856b652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Positive-QTOFsplash10-074u-9500000000-c4e4ed6470c8ad78afec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Positive-QTOFsplash10-0006-9000000000-8214c2f0d9df1ac7c79c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Positive-QTOFsplash10-022i-9400000000-257f9838bad9d558822c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Negative-QTOFsplash10-0006-9000000000-2e8bea71938b0c3ee5482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Negative-QTOFsplash10-0006-9100000000-8cda59dcc275524136f42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-2ddb498acc970a567f6b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Positive-QTOFsplash10-03dl-5900000000-4b73ae512e57466dd4e62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Positive-QTOFsplash10-0006-9100000000-d6c31a36d6fe5c68d9e12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Negative-QTOFsplash10-0a4i-1900000000-c84801951eaa1da750f72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Negative-QTOFsplash10-0006-9000000000-4ae1d11ab20f903606c32016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Negative-QTOFsplash10-0006-9000000000-aec3a40befb20e60f21b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-b0c5e687f246809cdae92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 20V, Negative-QTOFsplash10-01ox-6900000000-cb60b796898e6ca4336d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 40V, Negative-QTOFsplash10-0006-9000000000-fccf5d7216b23cffed7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Dihydroorotic acid 10V, Positive-QTOFsplash10-06r6-0900000000-86736ae769db7bc83c232021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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
Reactions
L-Dihydroorotic acid + a quinone → Orotic acid + a quinoldetails
L-Dihydroorotic acid + Quinone → Orotic acid + Hydroquinonedetails
Enzyme Details
2. CAD protein
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