Showing metabocard for orotate (MMDBc0054616)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:21:22 UTC
Update Date2022-08-12 20:09:02 UTC
Metabolite IDMMDBc0054616
Metabolite Identification
Common Nameorotate
Descriptionorotate, also known as orotic acid, 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. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate. orotate is an extremely weak basic (essentially neutral) compound (based on its pKa). Orotic acid can be mutagenic in mammalian somatic cells. Orotic acid is a pyrimidinedione and a carboxylic acid. Orotic aciduria is a cause of megaloblastic anaemia. It is also mutagenic for bacteria and yeast. This also leads to an increased urinary orotic acid excretion, because the orotic acid is not being properly utilized and must be eliminated. It may be a symptom of an increased ammonia load due to a metabolic disorder, such as a urea cycle disorder.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fecfc62a840>


  Mrv1533004241518432D          

 11 11  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   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 N   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007fecfc62a840>

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3D SDF for #<Metabolite:0x00007fecfc62a840>

  Mrv1533004241518432D          

 11 11  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   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 N   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054616

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=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)/p-1

> <INCHI_KEY>
PXQPEWDEAKTCGB-UHFFFAOYSA-M

> <FORMULA>
C5H3N2O4

> <MOLECULAR_WEIGHT>
155.09

> <EXACT_MASS>
155.009830165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
12.013279121666386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-1.227664501

> <ALOGPS_LOGS>
-1.04

> <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>
-6.031557162374665

> <JCHEM_POLAR_SURFACE_AREA>
98.33000000000001

> <JCHEM_REFRACTIVITY>
44.111700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orotate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fecfc62a840>
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PDB for #<Metabolite:0x00007fecfc62a840>
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O-1
CONECT    1    2    7                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007fecfc62a840>
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SMILES for #<Metabolite:0x00007fecfc62a840>
[O-]C(=O)C1=CC(=O)NC(=O)N1
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INCHI for #<Metabolite:0x00007fecfc62a840>
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)/p-1
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Synonyms
ValueSource
Orotic acidGenerator
Molecular FormulaC5H3N2O4
Average Mass155.09
Monoisotopic Mass155.009830165
IUPAC Name2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
Traditional Nameorotate
CAS Registry NumberNot Available
SMILES
[O-]C(=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)/p-1
InChI KeyPXQPEWDEAKTCGB-UHFFFAOYSA-M