Showing metabocard for N(4)-acetylcytosine (MMDBc0056183)

Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:18:55 UTC
Update Date2025-10-07 16:09:37 UTC
Metabolite IDMMDBc0056183
Metabolite Identification
Common NameN(4)-acetylcytosine
DescriptionN(4)-acetylcytosine is a modified nucleobase belonging to the class of nucleosides, specifically a derivative of cytosine. Its chemical structure features an acetyl group attached to the nitrogen at the 4-position of the cytosine ring, which alters its properties and reactivity. This compound participates in various chemical reactions, including electrophilic glycosidation, where it reacts with silylated compounds in the presence of N-iodosuccinimide, as demonstrated in the literature (PMID:19749278 ). Additionally, N(4)-acetylcytosine can undergo further transformations, such as reacting with specific esters to yield complex derivatives, exemplified by the formation of (Z,E)-1-(2-carbethoxycyclopropropylidenemethyl)cytosine with a notable Z/E ratio (PMID:19333855 ). These reactions highlight the compound's versatility in synthetic organic chemistry and its potential roles in various biochemical pathways, including those related to nucleic acid metabolism and modification.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000564323749318>


  Mrv1652306172222182D          

 11 11  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  4  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000564323749318>

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3D SDF for #<Metabolite:0x0000564323749318>

  Mrv1652306172222182D          

 11 11  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  4  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056183

> <DATABASE_NAME>
MIME

> <SMILES>
CC(O)=NC1=NC(O)=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)

> <INCHI_KEY>
IJCKBIINTQEGLY-UHFFFAOYSA-N

> <FORMULA>
C6H7N3O2

> <MOLECULAR_WEIGHT>
153.141

> <EXACT_MASS>
153.053826477

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.265713881229761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-hydroxypyrimidin-4-yl)ethanimidic acid

> <JCHEM_LOGP>
0.984580724

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.14436152265306

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.530194051910509

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2082673704304283

> <JCHEM_POLAR_SURFACE_AREA>
78.60000000000001

> <JCHEM_REFRACTIVITY>
40.580799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-hydroxypyrimidin-4-yl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000564323749318>
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PDB for #<Metabolite:0x0000564323749318>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    1    8   10                                                  
CONECT    5    2    8    9                                                  
CONECT    6    7    9   11                                                  
CONECT    7    3    6                                                       
CONECT    8    4    5                                                       
CONECT    9    5    6                                                       
CONECT   10    4                                                            
CONECT   11    6                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x0000564323749318>
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SMILES for #<Metabolite:0x0000564323749318>
CC(O)=NC1=NC(O)=NC=C1
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INCHI for #<Metabolite:0x0000564323749318>
InChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)
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Synonyms
ValueSource
4-(Acetylamino)pyrimidine-2(1H)-oneChEBI
4-Acetylamino-1,2-dihydro-2-pyrimidoneChEBI
N-(1,2-Dihydro-2-oxo-4-pyrimidinyl)acetamideChEBI
N-AcetylcytosineChEBI
Molecular FormulaC6H7N3O2
Average Mass153.141
Monoisotopic Mass153.053826477
IUPAC NameN-(2-hydroxypyrimidin-4-yl)ethanimidic acid
Traditional NameN-(2-hydroxypyrimidin-4-yl)ethanimidic acid
CAS Registry NumberNot Available
SMILES
CC(O)=NC1=NC(O)=NC=C1
InChI Identifier
InChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChI KeyIJCKBIINTQEGLY-UHFFFAOYSA-N