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Showing NP-Card for Orotic acid (NP0000198)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:16:48 UTC
NP-MRD IDNP0000198
Natural Product DOIhttps://doi.org/10.57994/0811
Secondary Accession NumbersNone
Natural Product Identification
Common NameOrotic acid
DescriptionOrotic acid is classified as a pyrimidinemonocarboxylic acid. That is it is a uracil bearing a carboxy substituent at position C-6. It is also classified as a pyrimidinedione and a carboxylic acid. Orotic acid is a minor dietary constituent. Indeed, until it was realized that it could be synthesized by humans, orotic acid was known as vitamin B-13. The richest dietary sources of orotic acid are cow's milk and other dairy products as well as root vegetables such as carrots and beets. Dietary intake probably contributes to a basal rate of orotic acid excretion in urine because fasting decreases excretion by ~50%. However, it is now apparent that most urinary orotic acid is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyltransferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase (UMP synthase deficiency or orotic aciduria). This disorder prevents the conversion of orotic acid to UMP, and thus to other pyrimidines. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Indeed, urinary orotic acid is so markedly increased in individuals harboring a mutation in UMP synthase that orotic acid crystals can form in the urine. The urinary concentration of orotic acid in individuals suffering from orotic aciduria can be of the order of millimoles of orotic acid per millimole creatinine. By comparison, the urinary level in unaffected individuals is ~ 1 ¬umol/mmol creatinine (PMID: 17513443 ). Orotic aciduria is characterized by megaloblastic anemia and orotic acid crystalluria that is frequently associated with some degree of physical and mental retardation. These features respond to appropriate pyrimidine replacement therapy and most cases appear to have a good prognosis. When present in sufficiently high levels, orotic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of orotic acid are associated with at least seven inborn errors of metabolism, including argininemia, LPI syndrome (lysinuric protein intolerance), hyperornithinemia-hyperammonemia-homocitrullinuria (HHH), OTC deficiency, citrullinemia type I, purine nucleoside phosphorylase deficiency, and orotic aciduria. Orotic acid is broadly classified as an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000198 (Orotic acid)


  Mrv1652309032023582D          

 11 11  0  0  0  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  0  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
  2  4  1  0  0  0  0
  4  5  2  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
Download

3D MOL for NP0000198 (Orotic acid)

HMDB0000226
     RDKit          3D
Orotic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5704    1.0982    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.1371    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887   -0.8593   -0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054    0.1169    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148    1.1169    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    1.0640    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3373    1.9676    0.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    0.0091   -0.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2428   -0.9730   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246   -1.9599   -1.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -0.9229   -0.4544 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -1.0406   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786    1.9519    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866   -0.0189   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -1.6872   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  8 14  1  0
 11 15  1  0
M  END
Download

3D SDF for NP0000198 (Orotic acid)


  Mrv1652309032023582D          

 11 11  0  0  0  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  0  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
  2  4  1  0  0  0  0
  4  5  2  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>
NP0000198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(=O)NC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)

> <INCHI_KEY>
PXQPEWDEAKTCGB-UHFFFAOYSA-N

> <FORMULA>
C5H4N2O4

> <MOLECULAR_WEIGHT>
156.0963

> <EXACT_MASS>
156.017106626

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.461507679606417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-1.227664501

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.781577888084735

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.827266331449678

> <JCHEM_PKA_STRONGEST_BASIC>
-6.031557162374663

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
33.27460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orotic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000198 (Orotic acid)

HMDB0000226
     RDKit          3D
Orotic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5704    1.0982    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.1371    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887   -0.8593   -0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054    0.1169    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148    1.1169    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    1.0640    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3373    1.9676    0.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    0.0091   -0.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2428   -0.9730   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246   -1.9599   -1.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -0.9229   -0.4544 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -1.0406   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786    1.9519    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866   -0.0189   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -1.6872   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  8 14  1  0
 11 15  1  0
M  END
Download

PDB for NP0000198 (Orotic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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
Download

3D PDB for NP0000198 (Orotic acid)

COMPND    HMDB0000226
HETATM    1  O1  UNL     1       2.570   1.098   1.062  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.050   0.137   0.439  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.889  -0.859  -0.003  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.605   0.117   0.214  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.215   1.117   0.661  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.577   1.064   0.430  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.337   1.968   0.830  1.00  0.00           O  
HETATM    8  N1  UNL     1      -2.061   0.009  -0.241  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.243  -0.973  -0.677  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.725  -1.960  -1.309  1.00  0.00           O  
HETATM   11  N2  UNL     1       0.075  -0.923  -0.454  1.00  0.00           N  
HETATM   12  H1  UNL     1       3.152  -1.041  -0.944  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.179   1.952   1.193  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.087  -0.019  -0.408  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.723  -1.687  -0.792  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   11
CONECT    5    6   13
CONECT    6    7    7    8
CONECT    8    9   14
CONECT    9   10   10   11
CONECT   11   15
END
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SMILES for NP0000198 (Orotic acid)

OC(=O)C1=CC(=O)NC(=O)N1
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INCHI for NP0000198 (Orotic acid)

InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
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View in JSmol
Synonyms
ValueSource
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
Chemical FormulaC5H4N2O4
Average Mass156.0963 Da
Monoisotopic Mass156.01711 Da
IUPAC Name2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Traditional Nameorotic acid
CAS Registry Number65-86-1
SMILES
OC(=O)C1=CC(=O)NC(=O)N1
InChI Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
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Species Where Detected
Species NameSourceReference
Bos taurus domesticusKNApSAcK Database
Escherichia coliKNApSAcK Database
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point345.5 °CNot Available
Boiling Point656.00 to 657.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.82 mg/mL at 18 °CNot Available
LogP-0.83Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
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
HMDB IDHMDB0000226
DrugBank IDDB02262
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031072
KNApSAcK IDC00019689
Chemspider ID942
KEGG Compound IDC00295
BioCyc IDOROTATE
BiGG ID34527
Wikipedia LinkOrotic_acid
METLIN ID318
PubChem Compound967
PDB IDNot Available
ChEBI ID16742
Good Scents IDrw1099361
References
General References
  1. Zieve L: Conditional deficiencies of ornithine or arginine. J Am Coll Nutr. 1986;5(2):167-76. [PubMed:3088083 ]
  2. Visek WJ: Ammonia: its effects on biological systems, metabolic hormones, and reproduction. J Dairy Sci. 1984 Mar;67(3):481-98. [PubMed:6371080 ]
  3. Arranz JA, Riudor E, Rodes M, Roig M, Climent C, Rubio V, Sentis M, Burlina A: Optimization of allopurinol challenge: sample purification, protein intake control, and the use of orotidine response as a discriminative variable improve performance of the test for diagnosing ornithine carbamoyltransferase deficiency. Clin Chem. 1999 Jul;45(7):995-1001. [PubMed:10388475 ]
  4. Sugio K, Gazdar AF, Albores-Saavedra J, Kokkinakis DM: High yields of K-ras mutations in intraductal papillary mucinous tumors and invasive adenocarcinomas induced by N-nitroso(2-hydroxypropyl)(2-oxopropyl)amine in the pancreas of female Syrian hamsters. Carcinogenesis. 1996 Feb;17(2):303-9. [PubMed:8625455 ]
  5. Finkelstein JE, Hauser ER, Leonard CO, Brusilow SW: Late-onset ornithine transcarbamylase deficiency in male patients. J Pediatr. 1990 Dec;117(6):897-902. [PubMed:2246687 ]
  6. Harris ML, Oberholzer VG: Conditions affecting the colorimetry of orotic acid and orotidine in urine. Clin Chem. 1980 Mar;26(3):473-9. [PubMed:7363468 ]
  7. Jakobs C, Sweetman L, Nyhan WL, Gruenke L, Craig JC, Wadman SK: Stable isotope dilution analysis of orotic acid and uracil in amniotic fluid. Clin Chim Acta. 1984 Nov 15;143(2):123-33. [PubMed:6391739 ]
  8. Visek WJ: Arginine and disease states. J Nutr. 1985 Apr;115(4):532-41. [PubMed:3884753 ]
  9. Mizutani Y, Wada H, Fukushima M, Yoshida O, Nakanishi H, Li YN, Miki T: Prognostic significance of orotate phosphoribosyltransferase activity in bladder carcinoma. Cancer. 2004 Feb 15;100(4):723-31. [PubMed:14770427 ]
  10. Valik D, Sedova Z, Starha J, Zeman J, Hruba E, Dvorakova L: Acute hyperammonaemic encephalopathy in a female newborn caused by a novel, de novo mutation in the ornithine transcarbamylase gene. Acta Paediatr. 2004 May;93(5):710-1. [PubMed:15174800 ]
  11. Mills GC, Schmalstieg FC, Newkirk KE, Goldblum RM: Cytosine and orotic acid in urine of immunodeficient children. Clin Chem. 1979 Mar;25(3):419-24. [PubMed:262183 ]
  12. Paradis D, Giguere R, Auray-Blais C, Draper P, Lemieux B: An automated method for the determination of orotic acid in the urine of children being screened for metabolic disorders. Clin Biochem. 1980 Aug;13(4):160-3. [PubMed:7449082 ]
  13. Potter M, Hammond JW, Sim KG, Green AK, Wilcken B: Ornithine carbamoyltransferase deficiency: improved sensitivity of testing for protein tolerance in the diagnosis of heterozygotes. J Inherit Metab Dis. 2001 Feb;24(1):5-14. [PubMed:11286382 ]
  14. van Kuilenburg AB, van Lenthe H, Loffler M, van Gennip AH: Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clin Chem. 2004 Nov;50(11):2117-24. Epub 2004 Sep 16. [PubMed:15375016 ]
  15. Brosnan ME, Brosnan JT: Orotic acid excretion and arginine metabolism. J Nutr. 2007 Jun;137(6 Suppl 2):1656S-1661S. [PubMed:17513443 ]