MiMeDB: Showing metabocard for Orotidine (MMDBc0000368)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:16 UTC

Update Date

2024-04-30 19:31:56 UTC

Metabolite ID

MMDBc0000368

Metabolite Identification

Common Name

Orotidine

Description

Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a beta-N1-glycosidic bond. It is a water-soluble solid. Orotidine is found in bacteria, fungi, plants, and animals. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in the biosynthesis of pyrimidine nucleosides (cytidine and uridine) that are found in nucleic acids (as the nucleotides containing the bases cytosine and uracil). Orotidine itself is not a component of nucleic acid. Orotidine monophosphate (OMP) is converted to uridine monophosphate by OMP decarboxylase, which is inhibited by mononucleotide precursors. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine, which is one such inhibitor, indicating that the subject has increased DNA synthesis due to cancer. Orotidine was first isolated from a mutant strain of the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell (PMID: 14853953 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000788
     RDKit          3D
Orotidine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.1468    0.4429    2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    0.2711    1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.1448    2.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    0.2405    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008    0.4487   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.4556   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    0.6371   -1.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493    0.2621   -2.2024 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.0689   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -0.1047   -2.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.0431   -0.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.1962   -0.1742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9608    0.9143   -0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139    0.3139   -0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2356    1.0622    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3217    2.3988   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246   -1.1009    0.0834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8344   -2.0477   -0.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -0.9139    0.8832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4022   -2.2020    1.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    0.8059    3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048    0.6039    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.2648   -3.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.8122   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.3409   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240    0.9849    1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402    0.6243    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.5076   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.3668    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -2.3301   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -0.3383    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -2.4231    2.0750 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 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11  4  1  0
 19 12  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
 20 32  1  0
M  END

  Mrv1652305271900242D          

 20 21  0  0  1  0            999 V2000
   22.0177  -14.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1372  -14.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5826  -15.7379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9672  -15.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1141  -12.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5417  -12.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6851  -10.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2562  -13.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6851  -12.9759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3996  -11.7384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3526  -14.2859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.0976  -15.0704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6851  -13.8009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2726  -15.0704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.7877  -15.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9707  -12.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3996  -12.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9707  -11.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6851  -11.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2562  -12.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
 11  2  1  6  0  0  0
 12  3  1  6  0  0  0
  4 15  1  0  0  0  0
  5 17  2  0  0  0  0
  6 20  1  0  0  0  0
  7 19  2  0  0  0  0
  8 20  2  0  0  0  0
 13  9  1  1  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 17  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000368

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
FKCRAVPPBFWEJD-XVFCMESISA-N

> <FORMULA>
C10H12N2O8

> <MOLECULAR_WEIGHT>
288.2109

> <EXACT_MASS>
288.05936537

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.003434122411154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

> <ALOGPS_LOGP>
-2.04

> <JCHEM_LOGP>
-2.7876156426666667

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.682367621598052

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8566931418927357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980299871615192

> <JCHEM_POLAR_SURFACE_AREA>
156.63000000000002

> <JCHEM_REFRACTIVITY>
59.870900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orotidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000788
     RDKit          3D
Orotidine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.1468    0.4429    2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    0.2711    1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.1448    2.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    0.2405    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008    0.4487   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.4556   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    0.6371   -1.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493    0.2621   -2.2024 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.0689   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -0.1047   -2.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.0431   -0.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.1962   -0.1742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9608    0.9143   -0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139    0.3139   -0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2356    1.0622    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3217    2.3988   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246   -1.1009    0.0834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8344   -2.0477   -0.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -0.9139    0.8832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4022   -2.2020    1.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    0.8059    3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048    0.6039    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.2648   -3.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.8122   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.3409   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240    0.9849    1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402    0.6243    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.5076   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.3668    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -2.3301   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -0.3383    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -2.4231    2.0750 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 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11  4  1  0
 19 12  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
 20 32  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      41.100 -26.667   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.056 -26.191   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      44.021 -29.377   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      39.139 -29.216   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      45.013 -24.222   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      38.345 -23.452   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      42.346 -19.602   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      39.678 -25.762   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      42.346 -24.222   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      43.679 -21.912   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      43.592 -26.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.116 -28.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.346 -25.762   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      41.576 -28.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.670 -29.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      41.012 -23.452   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      43.679 -23.452   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.012 -21.912   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.346 -21.142   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.678 -24.222   0.000  0.00  0.00           C+0
CONECT    1   13   14                                                       
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5   17                                                            
CONECT    6   20                                                            
CONECT    7   19                                                            
CONECT    8   20                                                            
CONECT    9   13   16   17                                                  
CONECT   10   17   19                                                       
CONECT   11    2   12   13                                                  
CONECT   12    3   11   14                                                  
CONECT   13    1    9   11                                                  
CONECT   14    1   12   15                                                  
CONECT   15    4   14                                                       
CONECT   16    9   18   20                                                  
CONECT   17    5    9   10                                                  
CONECT   18   16   19                                                       
CONECT   19    7   10   18                                                  
CONECT   20    6    8   16                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0000788
HETATM    1  O1  UNL     1       3.147   0.443   2.590  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.109   0.271   1.855  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.978   0.145   2.549  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.283   0.240   0.449  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.601   0.449  -0.040  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.863   0.456  -1.375  1.00  0.00           C  
HETATM    7  O3  UNL     1       5.016   0.637  -1.810  1.00  0.00           O  
HETATM    8  N1  UNL     1       2.849   0.262  -2.202  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.627   0.069  -1.725  1.00  0.00           C  
HETATM   10  O4  UNL     1       0.734  -0.105  -2.632  1.00  0.00           O  
HETATM   11  N2  UNL     1       1.260   0.043  -0.388  1.00  0.00           N  
HETATM   12  C6  UNL     1      -0.080  -0.196  -0.174  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.961   0.914  -0.330  1.00  0.00           O  
HETATM   14  C7  UNL     1      -2.214   0.314  -0.472  1.00  0.00           C  
HETATM   15  C8  UNL     1      -3.236   1.062   0.391  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.322   2.399  -0.008  1.00  0.00           O  
HETATM   17  C9  UNL     1      -2.125  -1.101   0.083  1.00  0.00           C  
HETATM   18  O7  UNL     1      -1.834  -2.048  -0.867  1.00  0.00           O  
HETATM   19  C10 UNL     1      -0.762  -0.914   0.883  1.00  0.00           C  
HETATM   20  O8  UNL     1      -0.402  -2.202   1.159  1.00  0.00           O  
HETATM   21  H1  UNL     1       0.652   0.806   3.230  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.405   0.604   0.672  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.036   0.265  -3.260  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.419  -0.812  -1.131  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.500   0.341  -1.529  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.924   0.985   1.448  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.240   0.624   0.283  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.037   2.508  -0.948  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.920  -1.367   0.772  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.685  -2.330  -1.283  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.205  -0.338   1.734  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.696  -2.423   2.075  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7    7    8
CONECT    8    9   23
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   19   24
CONECT   13   14
CONECT   14   15   17   25
CONECT   15   16   26   27
CONECT   16   28
CONECT   17   18   19   29
CONECT   18   30
CONECT   19   20   31
CONECT   20   32
END

HMDB0000788
     RDKit          3D
Orotidine
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.1468    0.4429    2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    0.2711    1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.1448    2.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    0.2405    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008    0.4487   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.4556   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    0.6371   -1.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493    0.2621   -2.2024 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.0689   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -0.1047   -2.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.0431   -0.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.1962   -0.1742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9608    0.9143   -0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139    0.3139   -0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2356    1.0622    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3217    2.3988   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246   -1.1009    0.0834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8344   -2.0477   -0.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -0.9139    0.8832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4022   -2.2020    1.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    0.8059    3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048    0.6039    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.2648   -3.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.8122   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.3409   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240    0.9849    1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402    0.6243    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.5076   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.3668    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -2.3301   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -0.3383    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -2.4231    2.0750 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 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11  4  1  0
 19 12  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
 20 32  1  0
M  END

Synonyms

Value	Source
3-Ribofuranosylorotic acid	ChEBI
6-Carboxyuridine	ChEBI
3-Ribofuranosylorotate	Generator
Orotic acid riboside	HMDB
Orotidine, ammonium salt	HMDB

Molecular Formula

C₁₀H₁₂N₂O₈

Average Mass

288.2109

Monoisotopic Mass

288.05936537

IUPAC Name

3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

Traditional Name

orotidine

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O

InChI Identifier

InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1

InChI Key

FKCRAVPPBFWEJD-XVFCMESISA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i3-9230000000-e2c457e981d3f20213c6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-03ei-4340390000-f308e272596bbf4876aa	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f92-6790000000-22b02fcae382ac45192a	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0940000000-ae1aee48fbe832808af5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1920000000-8d5291c4fd7f7d30f0bb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-8900000000-b3e3dadd94fb667cbb00	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052o-3970000000-a100d1c804d27c0b6e97	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0910000000-1a9d30040efa9eecd74d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9600000000-001a262ee2894d294d1c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910000000-db12fcd4210da39a9371	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ri-0910000000-cb586e3766ceeef71494	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3900000000-7e74435ea88ec8add7cb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0190000000-5c6d124476de69b9c589	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-1940000000-64fcb770cc2756bd0348	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-6b704e1f9de9d9c4d8f6	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Orotidine (MMDBc0000368)

MOL for #<Metabolite:0x00007fb80858a5d0>

3D MOL for #<Metabolite:0x00007fb80858a5d0>

3D SDF for #<Metabolite:0x00007fb80858a5d0>

3D-SDF for #<Metabolite:0x00007fb80858a5d0>

PDB for #<Metabolite:0x00007fb80858a5d0>

3D PDB for #<Metabolite:0x00007fb80858a5d0>

SMILES for #<Metabolite:0x00007fb80858a5d0>

INCHI for #<Metabolite:0x00007fb80858a5d0>

Structure for #<Metabolite:0x00007fb80858a5d0>

3D Structure for #<Metabolite:0x00007fb80858a5d0>