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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-02-04 15:11:57 UTC

Update Date

2022-09-22 18:34:20 UTC

HMDB ID

HMDB0011691

Secondary Accession Numbers

HMDB11691

Metabolite Identification

Common Name

Cytidine 2',3'-cyclic phosphate

Description

Cytidine 2',3'-cyclic phosphate is a cytidine nucleotide containing a pyrophosphate group esterified to C2 and C3(cyclic) of the sugar moiety. A cyclic nucleotide is any nucleotide in which the phosphate group is bonded to two of the sugar's hydroxyl groups, forming a cyclical or ring structure. 2',3' cyclic CMP is a substrate for 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). This enzyme (also called CNP) catalyzes the chemical reaction: nucleoside 2',3'-cyclic phosphate + H2O <-> nucleoside 2'-phosphate. CNP is a myelin-associated enzyme that makes up 4% of total CNS myelin protein, and is thought to undergo significant age-associated changes. The absence of CNP causes axonal swelling and neuronal degeneration. The biological role of cyclic 2',3' monophosphates is not clear, although it is thought to have something to do with neuronal stasis or development.

Structure

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

HMDB0011691
     RDKit          3D
Cytidine 2',3'-cyclic phosphate
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.4361   -0.9862   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -0.6220   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.1677    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666    0.5332    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.1409    0.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931    0.5438    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068    0.9059   -0.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9425    0.9784   -0.5978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4157    2.4072   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    2.3536   -0.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970    0.2992    0.7385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1723   -0.5209    0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6623   -1.9332    0.0733 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3739   -2.0772   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8710   -3.2298    1.1021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0089   -1.5658   -0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -0.5438    0.7487 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8288   -0.6320   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.9962   -1.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -1.0071   -1.1572 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494   -0.2128   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7810   -1.9559   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    0.4891    1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    1.1518    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    1.3918    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    0.5133   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.8414    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766    3.0180   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    2.4468   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9870    1.0319    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -4.0732    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.8580    1.7531 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
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  2  0
 17  6  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 15 31  1  0
 17 32  1  1
M  END


  Mrv0541 02241201502D          

 20 22  0  0  1  0            999 V2000
   10.3600   -7.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5316   -8.2555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5754   -7.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9185   -8.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9624   -7.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1339   -8.5526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0900   -9.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3162   -8.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9837   -8.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5712   -9.2950    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6511   -8.5104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3962   -9.2950    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1778   -7.4907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3162  -10.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6511  -10.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4357   -8.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6073   -7.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9837  -10.5646    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3962  -11.2791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5712  -11.2791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  2  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
  2  8  1  0  0  0  0
 13  5  1  0  0  0  0
 10 14  1  1  0  0  0
 12 15  1  1  0  0  0
 11 16  1  6  0  0  0
 17 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011691

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N3O7P/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14)/t4-,6-,7-,8?/m1/s1

> <INCHI_KEY>
NMPZCCZXCOMSDQ-ZRTZXPPTSA-N

> <FORMULA>
C9H12N3O7P

> <MOLECULAR_WEIGHT>
305.1812

> <EXACT_MASS>
305.041286265

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.76071278729555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-amino-1,2-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
-1.78

> <JCHEM_LOGP>
-2.2562422969105067

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.584903044550341

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.6486125153578648

> <JCHEM_PKA_STRONGEST_BASIC>
1.764223084638504

> <JCHEM_POLAR_SURFACE_AREA>
143.91

> <JCHEM_REFRACTIVITY>
61.6387

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-aminopyrimidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011691
     RDKit          3D
Cytidine 2',3'-cyclic phosphate
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.4361   -0.9862   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -0.6220   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.1677    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666    0.5332    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.1409    0.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931    0.5438    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068    0.9059   -0.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9425    0.9784   -0.5978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4157    2.4072   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    2.3536   -0.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970    0.2992    0.7385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1723   -0.5209    0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6623   -1.9332    0.0733 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3739   -2.0772   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8710   -3.2298    1.1021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0089   -1.5658   -0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -0.5438    0.7487 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8288   -0.6320   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.9962   -1.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -1.0071   -1.1572 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494   -0.2128   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7810   -1.9559   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    0.4891    1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    1.1518    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    1.3918    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    0.5133   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.8414    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766    3.0180   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    2.4468   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9870    1.0319    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -4.0732    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.8580    1.7531 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
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  2  0
 17  6  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 15 31  1  0
 17 32  1  1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.339 -13.904   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      19.659 -15.410   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      17.874 -13.428   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.515 -16.441   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.730 -14.458   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      17.050 -15.965   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      18.835 -17.947   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      21.124 -15.886   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      22.370 -14.981   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      21.600 -17.351   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.615 -15.886   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.140 -17.351   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      15.265 -13.983   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      21.124 -18.815   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      23.615 -18.815   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      25.080 -15.410   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      25.400 -13.904   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      22.370 -19.721   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      23.140 -21.054   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      21.600 -21.054   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3    6   13                                                  
CONECT    6    4    5                                                       
CONECT    7    4                                                            
CONECT    8    9   10    2                                                  
CONECT    9    8   11                                                       
CONECT   10    8   12   14                                                  
CONECT   11    9   12   16                                                  
CONECT   12   10   11   15                                                  
CONECT   13    5                                                            
CONECT   14   10   18                                                       
CONECT   15   12   18                                                       
CONECT   16   11   17                                                       
CONECT   17   16                                                            
CONECT   18   19   20   14   15                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0011691
HETATM    1  N1  UNL     1       5.436  -0.986  -0.393  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.073  -0.622  -0.282  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.690   0.168   0.775  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.367   0.533   0.901  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.413   0.141   0.013  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.093   0.544   0.196  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.607   0.906  -0.946  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.943   0.978  -0.598  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.416   2.407  -0.434  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.767   2.354  -0.086  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.097   0.299   0.738  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.172  -0.521   0.847  1.00  0.00           O  
HETATM   13  P1  UNL     1      -2.662  -1.933   0.073  1.00  0.00           P  
HETATM   14  O4  UNL     1      -3.374  -2.077  -1.236  1.00  0.00           O  
HETATM   15  O5  UNL     1      -2.871  -3.230   1.102  1.00  0.00           O  
HETATM   16  O6  UNL     1      -1.009  -1.566  -0.157  1.00  0.00           O  
HETATM   17  C8  UNL     1      -0.837  -0.544   0.749  1.00  0.00           C  
HETATM   18  C9  UNL     1       1.829  -0.632  -1.008  1.00  0.00           C  
HETATM   19  O7  UNL     1       0.944  -0.996  -1.832  1.00  0.00           O  
HETATM   20  N3  UNL     1       3.125  -1.007  -1.157  1.00  0.00           N  
HETATM   21  H1  UNL     1       6.149  -0.213  -0.424  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.781  -1.956  -0.447  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.451   0.489   1.496  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.098   1.152   1.739  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.005   1.392   0.910  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.561   0.513  -1.378  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.891   2.841   0.463  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.277   3.018  -1.325  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.361   2.447  -0.863  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.987   1.032   1.565  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.083  -4.073   0.672  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.539  -0.858   1.753  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   20   20
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6   18
CONECT    6    7   17   25
CONECT    7    8
CONECT    8    9   11   26
CONECT    9   10   27   28
CONECT   10   29
CONECT   11   12   17   30
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   31
CONECT   16   17
CONECT   17   32
CONECT   18   19   19   20
END

HMDB0011691
     RDKit          3D
Cytidine 2',3'-cyclic phosphate
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.4361   -0.9862   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -0.6220   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.1677    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666    0.5332    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.1409    0.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931    0.5438    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068    0.9059   -0.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9425    0.9784   -0.5978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4157    2.4072   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    2.3536   -0.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970    0.2992    0.7385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1723   -0.5209    0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6623   -1.9332    0.0733 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3739   -2.0772   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8710   -3.2298    1.1021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0089   -1.5658   -0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -0.5438    0.7487 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8288   -0.6320   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.9962   -1.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -1.0071   -1.1572 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494   -0.2128   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7810   -1.9559   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    0.4891    1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    1.1518    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    1.3918    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    0.5133   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.8414    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766    3.0180   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    2.4468   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9870    1.0319    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -4.0732    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.8580    1.7531 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
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  2  0
 17  6  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 15 31  1  0
 17 32  1  1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cytidine 2',3'-cyclic phosphoric acid	Generator
2',3' Cyclic CMP	HMDB
2',3' Cyclic-CMP	HMDB
Cyclic(2',3')-CMP	HMDB
Cytidine-2',3'-cyclophosphate	HMDB

Chemical Formula

C₉H₁₂N₃O₇P

Average Molecular Weight

305.1812

Monoisotopic Molecular Weight

305.041286265

IUPAC Name

1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-amino-1,2-dihydropyrimidin-2-one

Traditional Name

1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-aminopyrimidin-2-one

CAS Registry Number

15718-51-1

SMILES

NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

InChI Identifier

InChI=1S/C9H12N3O7P/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14)/t4-,6-,7-,8?/m1/s1

InChI Key

NMPZCCZXCOMSDQ-ZRTZXPPTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2',3'-cyclic pyrimidine nucleotides. These are pyrimidine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Cyclic pyrimidine nucleotides

Direct Parent

2',3'-cyclic pyrimidine nucleotides

Alternative Parents

Substituents

2',3'-cyclic pyrimidine ribonucleotide
Ribonucleoside 3'-phosphate
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Pyrimidine
Imidolactam
Heteroaromatic compound
Tetrahydrofuran
1,3_dioxaphospholane
Organoheterocyclic compound
Oxacycle
Azacycle
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic nitrogen compound
Primary amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Placenta (HMDB: HMDB0011691)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0011691)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	162.254	30932474
[M-H]-	Not Available	161.447	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000143
[M+H]+	Not Available	162.482	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000143

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.5 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-0.65	ChemAxon
pKa (Strongest Basic)	1.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	143.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.64 m³·mol⁻¹	ChemAxon
Polarizability	25.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.054	31661259
DarkChem	[M-H]-	162.86	31661259
DeepCCS	[M-2H]-	185.181	30932474
DeepCCS	[M+Na]+	161.099	30932474
AllCCS	[M+H]+	165.9	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.0	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.52 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7218 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	328.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	400.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	57.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	243.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	771.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	549.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	586.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	652.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	420.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	343.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cytidine 2',3'-cyclic phosphate	NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12	3585.2	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate	NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12	2527.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate	NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12	3076.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cytidine 2',3'-cyclic phosphate,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	2770.2	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,1TMS,isomer #2	C[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N)=NC3=O)O[C@H](CO)[C@H]2O1	2774.7	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,1TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	2824.7	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	2779.9	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	2805.4	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	3897.5	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	2838.7	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	2801.7	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	3957.7	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	2834.6	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	2810.7	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	3762.3	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C	2798.8	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C	2868.5	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C	3930.6	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	2867.5	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	2869.8	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@@H]23)C=C1	3571.7	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	2797.8	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	2907.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	3613.2	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	2822.6	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	2931.5	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	3452.1	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	2837.1	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	2944.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	3283.4	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	2988.8	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N)=NC3=O)O[C@H](CO)[C@H]2O1	3003.4	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	3083.3	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	3191.4	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	3228.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	4041.5	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	3294.0	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	3270.5	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O)O[C@@H]23)C=C1	4053.2	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3311.1	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3245.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3922.0	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C(C)(C)C	3224.4	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C(C)(C)C	3305.8	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C2O[C@H](CO)[C@H]3OP(=O)(O)O[C@@H]23)C=C1)[Si](C)(C)C(C)(C)C	3957.0	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3504.3	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3470.1	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@@H]23)C=C1	3826.1	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	3432.4	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	3543.1	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O)O[C@H]12	3776.6	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	3421.6	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	3522.2	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)O[C@H]2C(N3C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC3=O)O[C@H](CO)[C@H]2O1	3664.4	Standard polar	33892256
Cytidine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	3582.0	Semi standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	3712.6	Standard non polar	33892256
Cytidine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]12	3576.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine 2',3'-cyclic phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rx-5940000000-8ab4c4a156dd13eee927	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine 2',3'-cyclic phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3913000000-33e0f0bba64d9939e84e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cytidine 2',3'-cyclic phosphate 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 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-03di-0901000000-f9f0fdfd685c0f6d0009	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-03di-0900000000-dad12eb9fc7a3373782c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 35V, Negative-QTOF	splash10-03di-0900000000-6e1a86cabcec8891dda9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-03di-4900000000-aecd73e537bb4318b1c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-03di-1900000000-b74f28f59440ae1f96f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-03di-3900000000-9cc2cbbabcad93d3efec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-03di-0900000000-72e18b487faf7c919791	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 35V, Positive-QTOF	splash10-03di-0900000000-3b3614c0d13e95e4d276	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Negative-QTOF	splash10-03di-0900000000-15c4e619992ee25f8e94	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Negative-QTOF	splash10-03di-0901000000-7ef02eb4f51fe6099399	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Negative-QTOF	splash10-03xu-9600000000-2921e887ac0b2dfcf98e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-03di-0901000000-e7f102f4bea63f5e5fda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-03di-2900000000-cb3d80cc5dffe05f6888	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-03di-9600000000-6f0a550e121f5621a2f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Negative-QTOF	splash10-0nmi-1394000000-318f2cd988d67fcae4ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Negative-QTOF	splash10-03di-7971000000-a038ae20ec94c0e427e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Negative-QTOF	splash10-0006-9100000000-a171fcfbd0db4fdcd822	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Negative-QTOF	splash10-0w29-0409000000-f8f0a161b78ae9d4d448	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Negative-QTOF	splash10-01ox-9543000000-63b886b4a09466e8c05b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Negative-QTOF	splash10-000x-9250000000-0c74f4f2bc95cd02b0f7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-03di-0903000000-88b3fcac211e9ba6e75e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-03di-1902000000-4245b167806855aff9e7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cytidine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-03di-4920000000-8f8af5c215ccf5b8e0d2	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028378

KNApSAcK ID

Not Available

Chemspider ID

35032090

KEGG Compound ID

C00127

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glutathione disulfide

METLIN ID

Not Available

PubChem Compound

53481030

PDB ID

Not Available

ChEBI ID

177258

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]

Enzymes

Enzyme Details

1. 2',3'-cyclic-nucleotide 3'-phosphodiesterase

General function:: Involved in 2',3'-cyclic-nucleotide 3'-phosphodiesterase activity
Specific function:: May participate in RNA metabolism in the myelinating cell, CNP is the third most abundant protein in central nervous system myelin (By similarity).
Gene Name:: CNP
Uniprot ID:: P09543
Molecular weight:: 47578.22

Showing metabocard for Cytidine 2',3'-cyclic phosphate (HMDB0011691)

MOL for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

3D MOL for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

3D SDF for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

3D-SDF for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

PDB for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

3D PDB for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

SMILES for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

INCHI for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

Structure for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

3D Structure for HMDB0011691 (Cytidine 2',3'-cyclic phosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes