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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (39) Show 39 proteins XML

enzymes (39) Show 39 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:48:15 UTC

HMDB ID

HMDB0000095

Secondary Accession Numbers

HMDB00095

Metabolite Identification

Common Name

Cytidine monophosphate

Description

Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991 ].

Structure

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

HMDB0000095
     RDKit          3D
Cytidine monophosphate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -6.0721   -1.3481    0.0712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7388   -0.8545   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211   -0.1936    0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.2767    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316    0.1057   -0.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981    0.5652   -0.5093 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1428   -0.4482   -0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.2285   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5163   -0.6583   -0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    0.0998   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8341    0.0736 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.8768   -0.0312    1.0494 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9306   -1.2491   -1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.3001    0.8105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    1.4004    0.2946 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4253    2.6088   -0.3771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588    1.3619    0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7997    2.6307    0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -0.5404   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351   -0.7186   -2.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -1.0074   -1.1789 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -2.1183    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8294   -0.9271   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -0.0495    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3627    0.7865    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    1.2085   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088    0.5820   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550   -1.4697   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.1263    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759   -0.5721   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -2.7214    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    1.3170    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887    2.4761   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    0.8036    1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946    2.7168   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  2  0
 17  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  8 27  1  6
  9 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
M  END


  Mrv1652308122017352D          

 21 22  0  0  0  0            999 V2000
 9999.142810001.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.934510001.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4054 9999.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.120010000.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8367 9999.6744    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10002.4236 9998.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.553410000.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.2519 9998.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.918210000.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4865 9998.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.918210000.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2037 9999.6733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2037 9998.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9182 9998.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6327 9998.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6327 9999.6733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0221 9999.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.354710000.0786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.609610000.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.434610000.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.689510000.0786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 16  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 19  1  1  6  0  0  0
 21  3  1  1  0  0  0
 20  2  1  6  0  0  0
 18 16  1  1  0  0  0
 11  9  2  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000095

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
IERHLVCPSMICTF-XVFCMESISA-N

> <FORMULA>
C9H14N3O8P

> <MOLECULAR_WEIGHT>
323.1965

> <EXACT_MASS>
323.051850951

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.90371152495837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-3.1532002531788748

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.25132029166282

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2475570725319463

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1523566621246245

> <JCHEM_POLAR_SURFACE_AREA>
175.13999999999996

> <JCHEM_REFRACTIVITY>
65.4177

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cytidine monophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000095
     RDKit          3D
Cytidine monophosphate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -6.0721   -1.3481    0.0712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7388   -0.8545   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211   -0.1936    0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.2767    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316    0.1057   -0.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981    0.5652   -0.5093 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1428   -0.4482   -0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.2285   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5163   -0.6583   -0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    0.0998   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8341    0.0736 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.8768   -0.0312    1.0494 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9306   -1.2491   -1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.3001    0.8105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    1.4004    0.2946 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4253    2.6088   -0.3771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588    1.3619    0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7997    2.6307    0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -0.5404   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351   -0.7186   -2.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -1.0074   -1.1789 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -2.1183    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8294   -0.9271   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -0.0495    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3627    0.7865    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    1.2085   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088    0.5820   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550   -1.4697   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.1263    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759   -0.5721   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -2.7214    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    1.3170    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887    2.4761   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    0.8036    1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946    2.7168   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  2  0
 17  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  8 27  1  6
  9 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
M  END

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  O   UNK     0    8665.0678669.535   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.4118669.519   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.2908666.059   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6248666.828   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8671.9628666.059   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8671.1918664.723   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8673.3008666.828   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8672.7378664.723   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8662.7818668.370   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8660.1088663.743   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8662.7818666.827   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.4478666.057   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8661.4478664.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7818663.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.1148664.517   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8664.1148666.057   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0    8666.7088665.908   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8665.4628666.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9388668.278   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.4788668.278   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.9548666.813   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4   21                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   11                                                            
CONECT   10   13                                                            
CONECT   11   12   16    9                                                  
CONECT   12   11   13                                                       
CONECT   13   14   12   10                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15   18                                                  
CONECT   17   18   21                                                       
CONECT   18   19   17   16                                                  
CONECT   19   18   20    1                                                  
CONECT   20   19   21    2                                                  
CONECT   21   20   17    3                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0000095
HETATM    1  N1  UNL     1      -6.072  -1.348   0.071  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.739  -0.854  -0.050  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.121  -0.194   0.992  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.819   0.277   0.843  1.00  0.00           C  
HETATM    5  N2  UNL     1      -2.132   0.106  -0.301  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.798   0.565  -0.509  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.143  -0.448  -0.612  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.340   0.229  -0.626  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.516  -0.658  -0.275  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.691   0.100  -0.310  1.00  0.00           O  
HETATM   11  P1  UNL     1       5.040  -0.834   0.074  1.00  0.00           P  
HETATM   12  O3  UNL     1       5.877  -0.031   1.049  1.00  0.00           O  
HETATM   13  O4  UNL     1       5.931  -1.249  -1.302  1.00  0.00           O  
HETATM   14  O5  UNL     1       4.572  -2.300   0.810  1.00  0.00           O  
HETATM   15  C7  UNL     1       1.232   1.400   0.295  1.00  0.00           C  
HETATM   16  O6  UNL     1       1.425   2.609  -0.377  1.00  0.00           O  
HETATM   17  C8  UNL     1      -0.259   1.362   0.660  1.00  0.00           C  
HETATM   18  O7  UNL     1      -0.800   2.631   0.708  1.00  0.00           O  
HETATM   19  C9  UNL     1      -2.750  -0.540  -1.304  1.00  0.00           C  
HETATM   20  O8  UNL     1      -2.135  -0.719  -2.392  1.00  0.00           O  
HETATM   21  N3  UNL     1      -4.022  -1.007  -1.179  1.00  0.00           N  
HETATM   22  H1  UNL     1      -6.332  -2.118   0.719  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.829  -0.927  -0.510  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.662  -0.049   1.916  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.363   0.786   1.668  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.682   1.208  -1.406  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.509   0.582  -1.672  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.655  -1.470  -1.017  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.343  -1.126   0.702  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.876  -0.572  -2.011  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.337  -2.721   1.241  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.858   1.317   1.202  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.989   2.476  -1.202  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.324   0.804   1.598  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.495   2.717  -0.003  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3   21   21
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6   19
CONECT    6    7   17   26
CONECT    7    8
CONECT    8    9   15   27
CONECT    9   10   28   29
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   30
CONECT   14   31
CONECT   15   16   17   32
CONECT   16   33
CONECT   17   18   34
CONECT   18   35
CONECT   19   20   20   21
END

HMDB0000095
     RDKit          3D
Cytidine monophosphate
 35 36  0  0  0  0  0  0  0  0999 V2000
   -6.0721   -1.3481    0.0712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7388   -0.8545   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211   -0.1936    0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188    0.2767    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316    0.1057   -0.3009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981    0.5652   -0.5093 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1428   -0.4482   -0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.2285   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5163   -0.6583   -0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    0.0998   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8341    0.0736 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.8768   -0.0312    1.0494 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9306   -1.2491   -1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.3001    0.8105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    1.4004    0.2946 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4253    2.6088   -0.3771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588    1.3619    0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7997    2.6307    0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -0.5404   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351   -0.7186   -2.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -1.0074   -1.1789 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -2.1183    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8294   -0.9271   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -0.0495    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3627    0.7865    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    1.2085   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088    0.5820   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6550   -1.4697   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.1263    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759   -0.5721   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -2.7214    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576    1.3170    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887    2.4761   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    0.8036    1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946    2.7168   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  2  0
 17  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  8 27  1  6
  9 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CMP	ChEBI
Cytidine-5'-monophosphate	ChEBI
Cytidylate	ChEBI
Cytidylic acid	ChEBI
pC	ChEBI
Cytidine-5'-monophosphoric acid	Generator
Cytidine monophosphoric acid	Generator
Cytidine 5'-monophosphate	HMDB
Cytidine 5'-monophosphoric acid	HMDB
5'-CMP	HMDB
5-Cytidylate	HMDB
5-Cytidylic acid	HMDB
Cytidine 5'-monophosphorate	HMDB
Cytidine 5'-phosphate	HMDB
Cytidine 5'-phosphorate	HMDB
Cytidine 5'-phosphoric acid	HMDB
Cytidine mono(dihydrogen phosphate)	HMDB
Acid, cytidylic	HMDB
monoPhosphate, cytidine	HMDB
5’-CMP	HMDB
Cytidine 5’-monophosphate	HMDB
Cytidine 5’-monophosphoric acid	HMDB
Cytidine 5’-phosphate	HMDB
Cytidine 5’-phosphoric acid	HMDB
Cytidine monophosphate	HMDB
Cytosine 5'-monophosphate	HMDB
Cytosine 5’-monophosphate	HMDB

Chemical Formula

C₉H₁₄N₃O₈P

Average Molecular Weight

323.1965

Monoisotopic Molecular Weight

323.051850951

IUPAC Name

{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

cytidine monophosphate

CAS Registry Number

63-37-6

SMILES

NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

InChI Key

IERHLVCPSMICTF-XVFCMESISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside monophosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Aminopyrimidine
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Imidolactam
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Amine
Alcohol
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine ribonucleoside 5'-monophosphate (CHEBI:17361 )
cytidine 5'-phosphate (CHEBI:17361 )
Ribonucleotides (C00055 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Dihydropyrimidinase deficiency

Disposition

Biological location

Excreta

Feces

Cellular substructure

Macromolecular complex

Saliva

Organelle

Extracellular

Ingestion

Process

Naturally occurring process

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	233 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Spectral Properties

Experimental Collision Cross Sections

Predictor	Adduct Type	Data Source	CCS Value (Å²)	Reference
AllCCS	[M-H]-	Not Available	164.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000148
AllCCS	[M+H]+	Not Available	167.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000148

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.3 g/L	ALOGPS
logP	10^(-2) g/L	ALOGPS
logP	10^(-3.2) g/L	ChemAxon
logS	10^(-1.3) g/L	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	175.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.42 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.042	31661259
DarkChem	[M-H]-	167.429	31661259
AllCCS	[M+H]+	169.346	32859911
AllCCS	[M-H]-	164.391	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cytidine monophosphate,1TMS,#1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O	2794.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=CC(N)=NC1=O	2777.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O	2901.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#4	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1	2884.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C	2703.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O	2848.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#3	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1	2818.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=CC(N)=NC1=O	2834.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#5	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1	2803.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#6	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2890.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#7	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C1	2936.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#8	C[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C	2830.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O	3068.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=CC(N)=NC1=O	3045.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#3	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O	3140.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1	3143.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3195.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O	3300.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1	3288.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O	3290.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#5	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3271.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#6	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3338.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#7	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C1	3400.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#8	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C	3260.8	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9511000000-b038dcf334a34dfe4149	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine monophosphate GC-MS (2 TMS) - 70eV, Positive	splash10-01ot-9414000000-5835e3555d5546f12c1f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03di-0902000000-617172aee10f02d2ad2b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-03di-0900000000-ae1e8fc6db6222910637	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-03di-2900000000-c9ec8c41f82341b9225e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0229-0409000000-f28cc32ecb27c7712081	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF	splash10-03di-0902000000-9a79f63e713af4d035ab	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-03di-1900000000-a5ef2297cb197b2d13e2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-00ba-9003000000-fed24d718a29a060134b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-00ba-9003000000-331ea098a652ec08d560	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , negative-QTOF	splash10-00ba-9003000000-fed24d718a29a060134b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , negative-QTOF	splash10-00ba-9003000000-331ea098a652ec08d560	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOF	splash10-0229-0409000000-f28cc32ecb27c7712081	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOF	splash10-03di-0902000000-9a79f63e713af4d035ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOF	splash10-03di-1900000000-25254e2c3fbbfd5e145b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOF	splash10-03di-0900000000-54c9c74aa59c00f506b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate 30V, Positive-QTOF	splash10-03di-0902000000-9a79f63e713af4d035ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOF	splash10-03di-1900000000-263b7b1f82f6bb15409e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine monophosphate 40V, Positive-QTOF	splash10-03di-6900000000-b27523b9f2ac3b9d00b7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOF	splash10-03di-0901000000-75b42cbe789350bd13b0	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOF	splash10-03di-4900000000-fa026ae4d1a84f43102e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 40V, Positive-QTOF	splash10-03di-7900000000-5adaadd61efb1191857e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Negative-QTOF	splash10-0200-9848000000-0ac0c37265bd767019b2	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Negative-QTOF	splash10-004i-9200000000-5dd0a8c928cf323e5d75	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 40V, Negative-QTOF	splash10-004i-9000000000-73255a3373b4f1f51b4d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOF	splash10-03di-0911000000-88e415850bae3999df10	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOF	splash10-03di-0900000000-46d7ab7a98d3be427e4b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Mitochondria
Nucleus
Lysosome
Golgi apparatus

Biospecimen Locations

Feces
Saliva

Tissue Locations

All Tissues
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Pyrimidine metabolism	Not Available
Transcription/Translation	SMP00019	Not Available
Phosphatidylinositol Phosphate Metabolism
Plasmalogen Synthesis		Not Available
Pantothenate and CoA Biosynthesis

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	1.27 +/- 0.75 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	0.0573 +/- 0.176 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0965 +/- 0.0870 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected and Quantified	0.90 +/- 0.71 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	1.02 +/- 0.31 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	0.63 +/- 0.64 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]

Associated OMIM IDs

114500 (Colorectal cancer)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)

External Links

DrugBank ID

DB03403

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030736

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Cytidine monophosphate

METLIN ID

Not Available

PubChem Compound

6131

PDB ID

Not Available

ChEBI ID

17361

Food Biomarker Ontology

Not Available

VMH ID

CMP

MarkerDB ID

MDB00029866

Good Scents ID

Not Available

References

Synthesis Reference

Zhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hirono A, Fujii H, Miyajima H, Kawakatsu T, Hiyoshi Y, Miwa S: Three families with hereditary hemolytic anemia and pyrimidine 5'-nucleotidase deficiency: electrophoretic and kinetic studies. Clin Chim Acta. 1983 May 30;130(2):189-97. [PubMed:6307548 ]
Okahira S, Nishikawa F, Nishikawa S, Akazawa T, Seya T, Matsumoto M: Interferon-beta induction through toll-like receptor 3 depends on double-stranded RNA structure. DNA Cell Biol. 2005 Oct;24(10):614-23. [PubMed:16225392 ]
Daunter B, Newlands J: Seminal plasma biochemistry II: seminal plasma and spermatozoal cytidine monophosphate-sialic acid synthetase and sialyltransferase activities. Andrologia. 1981 May-Jun;13(3):215-24. [PubMed:6267956 ]
Schmukler M, Jewett PB, Levy CC: The effects of polyamines on a residue-specific human plasma ribonuclease. J Biol Chem. 1975 Mar 25;250(6):2206-12. [PubMed:234961 ]
Paglia DE, Valentine WN, Keitt AS, Brockway RA, Nakatani M: Pyrimidine nucleotidase deficiency with active dephosphorylation of dTMP: evidence for existence of thymidine nucleotidase in human erythrocytes. Blood. 1983 Nov;62(5):1147-9. [PubMed:6313098 ]
Yates AJ, Warner JK: Behavior of sugar derivatives in procedures for ganglioside isolation. Lipids. 1984 Jul;19(7):562-9. [PubMed:6748871 ]
Li YP, Curley G, Lopez M, Chavez M, Glew R, Aragon A, Kumar H, Baca OG: Protein-tyrosine phosphatase activity of Coxiella burnetii that inhibits human neutrophils. Acta Virol. 1996 Nov-Dec;40(5-6):263-72. [PubMed:9171454 ]
Hirono A, Fujii H, Natori H, Kurokawa I, Miwa S: Chromatographic analysis of human erythrocyte pyrimidine 5'-nucleotidase from five patients with pyrimidine 5'-nucleotidase deficiency. Br J Haematol. 1987 Jan;65(1):35-41. [PubMed:3028466 ]
Gella A, Ponce J, Cusso R, Durany N: Effect of the nucleotides CMP and UMP on exhaustion in exercise rats. J Physiol Biochem. 2008 Mar;64(1):9-17. [PubMed:18663991 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 39 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

Cytidine monophosphate + Water → Cytidine + Phosphate	details

Enzyme Details

2. UMP-CMP kinase

General function:: Involved in ATP binding
Specific function:: Catalyzes specific phosphoryl transfer from ATP to UMP and CMP.
Gene Name:: CMPK1
Uniprot ID:: P30085
Molecular weight:: 20180.12

Reactions

Adenosine triphosphate + Cytidine monophosphate → ADP + CDP	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

Cytidine monophosphate + Water → Cytidine + Phosphate	details

Enzyme Details

4. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

Cytidine monophosphate + Water → Cytidine + Phosphate	details

Enzyme Details

5. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

Cytidine monophosphate + Water → Cytidine + Phosphate	details

Enzyme Details

6. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Reactions

Cytidine monophosphate + Water → Cytidine + Phosphate	details

Enzyme Details

7. Ectonucleoside triphosphate diphosphohydrolase 1

General function:: Involved in hydrolase activity
Specific function:: In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:: ENTPD1
Uniprot ID:: P49961
Molecular weight:: 58706.0

Reactions

CDP + Water → Cytidine monophosphate + Phosphate	details

Enzyme Details

8. Soluble calcium-activated nucleotidase 1

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:: CANT1
Uniprot ID:: Q8WVQ1
Molecular weight:: 44839.24

Enzyme Details

9. Ectonucleoside triphosphate diphosphohydrolase 3

General function:: Involved in hydrolase activity
Specific function:: Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:: ENTPD3
Uniprot ID:: O75355
Molecular weight:: 59104.76

Reactions

CDP + Water → Cytidine monophosphate + Phosphate	details

Enzyme Details

10. Uridine-cytidine kinase 1

General function:: Involved in ATP binding
Specific function:: Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:: UCK1
Uniprot ID:: Q9HA47
Molecular weight:: 22760.43

Reactions

Adenosine triphosphate + Cytidine → ADP + Cytidine monophosphate	details
Uridine triphosphate + Cytidine → Uridine 5'-diphosphate + Cytidine monophosphate	details
Guanosine triphosphate + Cytidine → Guanosine diphosphate + Cytidine monophosphate	details
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphate	details
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphate	details
dGTP + Cytidine → dGDP + Cytidine monophosphate	details
Thymidine 5'-triphosphate + Cytidine → dTDP + Cytidine monophosphate	details
dCTP + Cytidine → dCDP + Cytidine monophosphate	details
Deoxyuridine triphosphate + Cytidine → dUDP + Cytidine monophosphate	details

Only showing the first 10 proteins. There are 39 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cytidine monophosphate (HMDB0000095)

MOL for HMDB0000095 (Cytidine monophosphate)

3D MOL for HMDB0000095 (Cytidine monophosphate)

3D SDF for HMDB0000095 (Cytidine monophosphate)

3D-SDF for HMDB0000095 (Cytidine monophosphate)

PDB for HMDB0000095 (Cytidine monophosphate)

3D PDB for HMDB0000095 (Cytidine monophosphate)

SMILES for HMDB0000095 (Cytidine monophosphate)

INCHI for HMDB0000095 (Cytidine monophosphate)

Structure for HMDB0000095 (Cytidine monophosphate)

3D Structure for HMDB0000095 (Cytidine monophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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