MiMeDB: Showing metabocard for N(4)-acetylcytidine (MMDBc0054596)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:20:09 UTC

Update Date

2024-10-17 18:17:36 UTC

Metabolite ID

MMDBc0054596

Metabolite Identification

Common Name

N(4)-acetylcytidine

Description

N4-Acetylcytidine is a modified nucleoside. N4-acetylcytidine is an endogenous urinary nucleoside product of the degradation of transfer ribonucleic acid (tRNA); urinary nucleosides are biological markers for patients with colorectal cancer. tRNA has been shown to be excreted in abnormal amounts in the urine of cancer patients. tRNA from neoplastic tissue had a much more rapid turnover rate than the tRNA from the corresponding normal tissue. Evidence indicates that methylation of tRNA occurs only after synthesis of the intact macromolecule. Because there are no specific enzyme systems to incorporate the modified nucleosides into the macromolecular nucleic acid, these nucleosides once released in the process of tRNA turnover cannot be reutilized, nor are they further degraded, but are excreted in urine. (PMID: 15991285 , 3506820 ).

Structure

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

HMDB0005923
     RDKit          3D
N4-Acetylcytidine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.7798    1.7350    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815    0.3889    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990    0.2250    1.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.6996    0.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5505    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -1.6638    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -1.5575    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3131   -0.3909   -0.2070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1899   -0.5622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7472    0.6217    0.3551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    0.6530   -0.2598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0474    1.2668    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    2.5598    0.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.8232   -0.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9187   -0.9713   -1.7770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -1.4204   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7364   -2.1804   -1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    0.6791   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.8197   -0.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403    0.5923    0.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3885    1.7026   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    2.0400    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    2.5029    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410   -1.6353    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -2.6098    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2043   -2.4127    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3177   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.2190   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1225    0.6199    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819    1.3208    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2769    3.0484    1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.2070    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -0.8145   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -2.0529    0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -2.1332   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20  5  2  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  6
 11 28  1  6
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 16 34  1  1
 17 35  1  0
M  END


  Mrv0541 02231220312D          

 20 21  0  0  1  0            999 V2000
   18.0922   -8.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9726   -8.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5273   -9.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1427   -9.8336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9958   -7.1578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8538   -4.6828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4247   -7.1578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7103   -5.9203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4247   -4.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7573   -8.4678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0122   -9.2525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4247   -7.9830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8372   -9.2525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3222   -9.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1392   -6.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7103   -6.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1392   -5.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4247   -5.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1392   -4.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1392   -3.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
 10  2  1  1  0  0  0
 11  3  1  1  0  0  0
  4 14  1  0  0  0  0
  5 16  2  0  0  0  0
  6 19  2  0  0  0  0
 12  7  1  6  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  2  0  0  0  0
  9 18  1  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054596

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N3O6/c1-5(16)12-7-2-3-14(11(19)13-7)10-9(18)8(17)6(4-15)20-10/h2-3,6,8-10,15,17-18H,4H2,1H3,(H,12,13,16,19)/t6-,8-,9-,10-/m1/s1

> <INCHI_KEY>
NIDVTARKFBZMOT-PEBGCTIMSA-N

> <FORMULA>
C11H15N3O6

> <MOLECULAR_WEIGHT>
285.2533

> <EXACT_MASS>
285.096085227

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.15696103091095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide

> <ALOGPS_LOGP>
-1.35

> <JCHEM_LOGP>
-2.866075645333333

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.218055184686406

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.465815760482243

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9784164756293983

> <JCHEM_POLAR_SURFACE_AREA>
131.69

> <JCHEM_REFRACTIVITY>
63.98860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N4-acetylcytidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005923
     RDKit          3D
N4-Acetylcytidine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.7798    1.7350    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815    0.3889    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990    0.2250    1.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.6996    0.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5505    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -1.6638    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -1.5575    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3131   -0.3909   -0.2070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1899   -0.5622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7472    0.6217    0.3551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    0.6530   -0.2598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0474    1.2668    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    2.5598    0.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.8232   -0.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9187   -0.9713   -1.7770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -1.4204   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7364   -2.1804   -1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    0.6791   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.8197   -0.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403    0.5923    0.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3885    1.7026   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    2.0400    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    2.5029    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410   -1.6353    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -2.6098    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2043   -2.4127    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3177   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.2190   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1225    0.6199    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819    1.3208    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2769    3.0484    1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.2070    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -0.8145   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -2.0529    0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -2.1332   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20  5  2  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  6
 11 28  1  6
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 16 34  1  1
 17 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.772 -15.807   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      29.816 -15.331   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.851 -18.517   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.733 -18.356   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      29.859 -13.361   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      35.194  -8.741   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      32.526 -13.361   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      31.193 -11.051   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      32.526  -8.741   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.280 -15.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.756 -17.271   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.526 -14.902   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.296 -17.271   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.201 -18.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.860 -12.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.193 -12.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.860 -11.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.526 -10.281   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.860  -7.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.860  -6.431   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5   16                                                            
CONECT    6   19                                                            
CONECT    7   12   15   16                                                  
CONECT    8   16   18                                                       
CONECT    9   18   19                                                       
CONECT   10    2   11   12                                                  
CONECT   11    3   10   13                                                  
CONECT   12    1    7   10                                                  
CONECT   13    1   11   14                                                  
CONECT   14    4   13                                                       
CONECT   15    7   17                                                       
CONECT   16    5    7    8                                                  
CONECT   17   15   18                                                       
CONECT   18    8    9   17                                                  
CONECT   19    6    9   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0005923
HETATM    1  C1  UNL     1       4.780   1.735   0.380  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.282   0.389   0.776  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.499   0.225   1.091  1.00  0.00           O  
HETATM    4  N1  UNL     1       4.391  -0.700   0.798  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.035  -0.550   0.454  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.187  -1.664   0.491  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.868  -1.558   0.165  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.313  -0.391  -0.207  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.046  -0.190  -0.562  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.747   0.622   0.355  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.000   0.653  -0.260  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.047   1.267   0.644  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.634   2.560   0.928  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.299  -0.823  -0.533  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.919  -0.971  -1.777  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.886  -1.420  -0.579  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.736  -2.180  -1.726  1.00  0.00           O  
HETATM   18  C11 UNL     1       1.140   0.679  -0.240  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.686   1.820  -0.582  1.00  0.00           O  
HETATM   20  N3  UNL     1       2.440   0.592   0.078  1.00  0.00           N  
HETATM   21  H1  UNL     1       4.389   1.703  -0.661  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.998   2.040   1.104  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.582   2.503   0.472  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.741  -1.635   1.073  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.611  -2.610   0.786  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.204  -2.413   0.190  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.181   0.318  -1.554  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.873   1.219  -1.207  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.123   0.620   1.538  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.982   1.321   0.065  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.277   3.048   1.511  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.888  -1.207   0.300  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.899  -0.814  -1.608  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.799  -2.053   0.308  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.809  -2.133  -2.012  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    4
CONECT    4    5   24
CONECT    5    6   20   20
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9   18
CONECT    9   10   16   27
CONECT   10   11
CONECT   11   12   14   28
CONECT   12   13   29   30
CONECT   13   31
CONECT   14   15   16   32
CONECT   15   33
CONECT   16   17   34
CONECT   17   35
CONECT   18   19   19   20
END

HMDB0005923
     RDKit          3D
N4-Acetylcytidine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.7798    1.7350    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815    0.3889    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990    0.2250    1.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -0.6996    0.7977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5505    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -1.6638    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -1.5575    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3131   -0.3909   -0.2070 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1899   -0.5622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7472    0.6217    0.3551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    0.6530   -0.2598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0474    1.2668    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    2.5598    0.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.8232   -0.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9187   -0.9713   -1.7770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -1.4204   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7364   -2.1804   -1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    0.6791   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.8197   -0.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403    0.5923    0.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3885    1.7026   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    2.0400    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    2.5029    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410   -1.6353    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   -2.6098    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2043   -2.4127    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    0.3177   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.2190   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1225    0.6199    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819    1.3208    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2769    3.0484    1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.2070    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -0.8145   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -2.0529    0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -2.1332   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20  5  2  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  6
 11 28  1  6
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  1
 15 33  1  0
 16 34  1  1
 17 35  1  0
M  END

Synonyms

Value	Source
4-Acetyl-1-(beta-D-ribofuranosyl)cytosine	ChEBI
N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide	ChEBI
4-Acetyl-1-(b-D-ribofuranosyl)cytosine	Generator
4-Acetyl-1-(β-D-ribofuranosyl)cytosine	Generator
4-Acetyl-1-(beta-delta-ribofuranosyl)cytosine	HMDB
4-Acetylcytidine	HMDB
N-4-Acetylcytidine	HMDB
N-Acetyl-cytidine	HMDB
N-Acetylcytidine	HMDB
Acetylcytidine	MeSH, HMDB

Molecular Formula

C₁₁H₁₅N₃O₆

Average Mass

285.2533

Monoisotopic Mass

285.096085227

IUPAC Name

N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide

Traditional Name

N4-acetylcytidine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H15N3O6/c1-5(16)12-7-2-3-14(11(19)13-7)10-9(18)8(17)6(4-15)20-10/h2-3,6,8-10,15,17-18H,4H2,1H3,(H,12,13,16,19)/t6-,8-,9-,10-/m1/s1

InChI Key

NIDVTARKFBZMOT-PEBGCTIMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine nucleosides

Alternative Parents

Substituents

Pyrimidine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrimidone
Hydropyrimidine
Monosaccharide
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Oxacycle
Azacycle
Carboximidic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

acetamides (CHEBI:70989 )
cytidines (CHEBI:70989 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	12.3 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.99 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avi-9260000000-457a65448f2b7f997b8e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00n0-7733900000-21a157f49e2b5c590e79	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0910000000-c60f41d3d945b79d13eb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0900000000-d9bb0feb4836d04f80b9	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0950000000-d29714fc1fde54480925	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2930000000-6f0a2c07a23e5a0c4ed8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uds-3900000000-79b2c1a24f98018ce91a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uec-0890000000-ae426cb4fd63f76b745c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1940000000-b5dd7d54b875099f3c73	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-b6b80dc5931b68b99826	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gx3-0960000000-77953fd09d47227f609c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-0900000000-f79c56b7470dab72e2e0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9700000000-2d2354944eb07a47ad15	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-1a973cafe87881a4871b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-540faca94381a3018323	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4900000000-56cd92e7d1e1be7080cd	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	80	Human ; Human feces; Chicken

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.560	0.108	uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	0.200	0.0600	uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0005923

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023789

KNApSAcK ID

Not Available

Chemspider ID

96702

KEGG Compound ID

Not Available

BioCyc ID

CPD-11648

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107461

PDB ID

Not Available

ChEBI ID

70989

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. doi: 10.1002/bmc.1130010305. [PubMed:3506820 ]
Zheng YF, Yang J, Zhao XJ, Feng B, Kong HW, Chen YJ, Lv S, Zheng MH, Xu GW: Urinary nucleosides as biological markers for patients with colorectal cancer. World J Gastroenterol. 2005 Jul 7;11(25):3871-6. doi: 10.3748/wjg.v11.i25.3871. [PubMed:15991285 ]
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 ]

Showing metabocard for N(4)-acetylcytidine (MMDBc0054596)

MOL for #<Metabolite:0x00007fab252b3018>

3D MOL for #<Metabolite:0x00007fab252b3018>

3D SDF for #<Metabolite:0x00007fab252b3018>

3D-SDF for #<Metabolite:0x00007fab252b3018>

PDB for #<Metabolite:0x00007fab252b3018>

3D PDB for #<Metabolite:0x00007fab252b3018>

SMILES for #<Metabolite:0x00007fab252b3018>

INCHI for #<Metabolite:0x00007fab252b3018>

Structure for #<Metabolite:0x00007fab252b3018>

3D Structure for #<Metabolite:0x00007fab252b3018>