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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015484

Secondary Accession Numbers

HMDB15484

Metabolite Identification

Common Name

Cefacetrile

Description

Cefacetrile is only found in individuals that have used or taken this drug. It is a derivative of 7-aminocephalosporanic acid.In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Structure

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

HMDB0015484
     RDKit          3D
Cefacetrile
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8797    0.5568   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4586    0.8836    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.6896   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801    0.2455    1.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4881    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    0.0252    0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8075   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390   -1.4874   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -1.4646   -0.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -2.2797   -1.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.1252   -0.4865 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -1.2060   -1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -1.2748   -2.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272   -1.1814   -0.6023 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9679    0.0746   -0.3951 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3630    0.1891   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.8215   -0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0441    1.4907   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4955    1.3446   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541    1.2125   -0.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -1.5914    0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128   -0.5963    1.9043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061    0.6928    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4144    0.3224    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867    1.4091   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9969   -0.3141   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    1.6659    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    0.3155    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409   -1.8449   -2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987   -2.0444   -0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    0.9166   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785    1.9092    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    2.2426   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -2.6770    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3152    1.1037    2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    1.4443    0.8393 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  3  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23  6  1  0
 21 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 14 30  1  6
 15 31  1  0
 18 32  1  0
 18 33  1  0
 21 34  1  1
 23 35  1  0
 23 36  1  0
M  END

1414
  Mrv0541 02231215282D          

 24 25  0  0  1  0            999 V2000
    5.2224   -1.3649    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3510    0.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3635   -0.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3510   -1.5404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3252   -1.4892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.9524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7688   -0.9558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7688   -0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1483   -1.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7305   -1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5278   -1.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1065   -1.5902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 16  1  0  0  0  0
  2 13  2  0  0  0  0
  3 17  1  0  0  0  0
  3 21  1  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6 19  2  0  0  0  0
  7 21  2  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
 12  9  1  1  0  0  0
  9 19  1  0  0  0  0
 10 22  3  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  6  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015484

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1

> <INCHI_KEY>
RRYMAQUWDLIUPV-BXKDBHETSA-N

> <FORMULA>
C13H13N3O6S

> <MOLECULAR_WEIGHT>
339.324

> <EXACT_MASS>
339.052505853

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.324019603805198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-1.780770973333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.224834187417505

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3054466250890515

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2268926534234135

> <JCHEM_POLAR_SURFACE_AREA>
136.8

> <JCHEM_REFRACTIVITY>
77.50560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cefacetrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015484
     RDKit          3D
Cefacetrile
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8797    0.5568   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4586    0.8836    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.6896   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801    0.2455    1.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4881    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    0.0252    0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8075   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390   -1.4874   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -1.4646   -0.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -2.2797   -1.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.1252   -0.4865 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -1.2060   -1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -1.2748   -2.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272   -1.1814   -0.6023 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9679    0.0746   -0.3951 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3630    0.1891   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.8215   -0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0441    1.4907   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4955    1.3446   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541    1.2125   -0.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -1.5914    0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128   -0.5963    1.9043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061    0.6928    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4144    0.3224    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867    1.4091   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9969   -0.3141   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    1.6659    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    0.3155    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409   -1.8449   -2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987   -2.0444   -0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    0.9166   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785    1.9092    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    2.2426   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -2.6770    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3152    1.1037    2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    1.4443    0.8393 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  3  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23  6  1  0
 21 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 14 30  1  6
 15 31  1  0
 18 32  1  0
 18 33  1  0
 21 34  1  1
 23 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1414                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.748  -2.548   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      13.722   0.860   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -0.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415   2.842   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.082   2.842   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      15.612  -0.993   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.414   2.072   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.082  -0.238   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.722  -2.875   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      19.274  -2.780   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.082  -1.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.635  -1.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.635  -0.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   0.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -0.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -1.778   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   0.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   2.072   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.210  -2.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.297  -3.571   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   0.532   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.785  -3.176   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -0.238   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      11.399  -2.968   0.000  0.00  0.00           H+0
CONECT    1   11   16                                                       
CONECT    2   13                                                            
CONECT    3   17   21                                                       
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7   21                                                            
CONECT    8   11   13   14                                                  
CONECT    9   12   19                                                       
CONECT   10   22                                                            
CONECT   11    1    8   12   24                                             
CONECT   12    9   11   13                                                  
CONECT   13    2    8   12                                                  
CONECT   14    8   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16    1   15                                                       
CONECT   17    3   15                                                       
CONECT   18    4    5   14                                                  
CONECT   19    6    9   20                                                  
CONECT   20   19   22                                                       
CONECT   21    3    7   23                                                  
CONECT   22   10   20                                                       
CONECT   23   21                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0015484
HETATM    1  C1  UNL     1      -5.880   0.557  -0.049  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.459   0.884   0.189  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.783   1.690  -0.487  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.780   0.245   1.266  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.473   0.488   1.555  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.277   0.025   0.947  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.100  -0.808  -0.047  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.139  -1.487  -0.779  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.341  -1.465  -0.553  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.795  -2.280  -1.895  1.00  0.00           O  
HETATM   11  N1  UNL     1       0.249  -1.125  -0.487  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.180  -1.206  -1.552  1.00  0.00           C  
HETATM   13  O5  UNL     1       1.147  -1.275  -2.818  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.327  -1.181  -0.602  1.00  0.00           C  
HETATM   15  N2  UNL     1       2.968   0.075  -0.395  1.00  0.00           N  
HETATM   16  C9  UNL     1       4.363   0.189  -0.442  1.00  0.00           C  
HETATM   17  O6  UNL     1       5.071  -0.822  -0.669  1.00  0.00           O  
HETATM   18  C10 UNL     1       5.044   1.491  -0.228  1.00  0.00           C  
HETATM   19  C11 UNL     1       6.495   1.345  -0.328  1.00  0.00           C  
HETATM   20  N3  UNL     1       7.654   1.212  -0.407  1.00  0.00           N  
HETATM   21  C12 UNL     1       1.269  -1.591   0.401  1.00  0.00           C  
HETATM   22  S1  UNL     1       1.213  -0.596   1.904  1.00  0.00           S  
HETATM   23  C13 UNL     1      -0.006   0.693   1.557  1.00  0.00           C  
HETATM   24  H1  UNL     1      -6.414   0.322   0.907  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.387   1.409  -0.570  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.997  -0.314  -0.739  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.439   1.666   1.632  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.370   0.316   2.732  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.541  -1.845  -2.774  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.999  -2.044  -0.806  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.394   0.917  -0.207  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.779   1.909   0.767  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.757   2.243  -1.020  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.277  -2.677   0.645  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.315   1.104   2.516  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.311   1.444   0.839  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   27   28
CONECT    6    7    7   23
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   29
CONECT   11   12   21
CONECT   12   13   13   14
CONECT   14   15   21   30
CONECT   15   16   31
CONECT   16   17   17   18
CONECT   18   19   32   33
CONECT   19   20   20   20
CONECT   21   22   34
CONECT   22   23
CONECT   23   35   36
END

HMDB0015484
     RDKit          3D
Cefacetrile
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.8797    0.5568   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4586    0.8836    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.6896   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801    0.2455    1.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4881    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    0.0252    0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8075   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390   -1.4874   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -1.4646   -0.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -2.2797   -1.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.1252   -0.4865 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -1.2060   -1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -1.2748   -2.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272   -1.1814   -0.6023 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9679    0.0746   -0.3951 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3630    0.1891   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.8215   -0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0441    1.4907   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4955    1.3446   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541    1.2125   -0.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -1.5914    0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128   -0.5963    1.9043 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061    0.6928    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4144    0.3224    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867    1.4091   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9969   -0.3141   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    1.6659    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    0.3155    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409   -1.8449   -2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987   -2.0444   -0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    0.9166   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785    1.9092    0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571    2.2426   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -2.6770    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3152    1.1037    2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    1.4443    0.8393 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  3  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23  6  1  0
 21 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 14 30  1  6
 15 31  1  0
 18 32  1  0
 18 33  1  0
 21 34  1  1
 23 35  1  0
 23 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cephacetrile	Kegg
Vetrimast	Kegg
7-Cyanacetylamino-cephalosporansaeure	HMDB
Cephacetrile sodium	HMDB
Celospor	HMDB
Sodium, cephacetrile	HMDB

Chemical Formula

C₁₃H₁₃N₃O₆S

Average Molecular Weight

339.324

Monoisotopic Molecular Weight

339.052505853

IUPAC Name

(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefacetrile

CAS Registry Number

10206-21-0

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O

InChI Identifier

InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1

InChI Key

RRYMAQUWDLIUPV-BXKDBHETSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporin 3'-esters

Alternative Parents

Substituents

Cephalosporin 3'-ester
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Meta-thiazine
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Dialkylthioether
Carbonitrile
Nitrile
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015484)
Membrane (HMDB: HMDB0015484)

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	2.43 g/L	Not Available
LogP	-0.45	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.43 g/L	ALOGPS
logP	-0.52	ALOGPS
logP	-1.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.8 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.51 m³·mol⁻¹	ChemAxon
Polarizability	31.32 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.833	31661259
DarkChem	[M-H]-	173.205	31661259
DeepCCS	[M-2H]-	208.183	30932474
DeepCCS	[M+Na]+	183.773	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	167.1	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cefacetrile	[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O	3997.7	Standard polar	33892256
Cefacetrile	[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O	2369.0	Standard non polar	33892256
Cefacetrile	[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O	2949.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cefacetrile,1TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)CC#N)[C@H]2SC1	2688.1	Semi standard non polar	33892256
Cefacetrile,1TMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C)[C@H]2SC1	2620.8	Semi standard non polar	33892256
Cefacetrile,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C)[C@H]2SC1	2596.2	Semi standard non polar	33892256
Cefacetrile,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C)[C@H]2SC1	2637.4	Standard non polar	33892256
Cefacetrile,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C)[C@H]2SC1	4397.8	Standard polar	33892256
Cefacetrile,1TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)CC#N)[C@H]2SC1	2857.8	Semi standard non polar	33892256
Cefacetrile,1TBDMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C(C)(C)C)[C@H]2SC1	2831.3	Semi standard non polar	33892256
Cefacetrile,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3027.2	Semi standard non polar	33892256
Cefacetrile,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3079.0	Standard non polar	33892256
Cefacetrile,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CC#N)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4288.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cefacetrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9431000000-03564927c39943abead9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefacetrile GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9112000000-6e8c2ec31c199d3db4e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefacetrile 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 10V, Positive-QTOF	splash10-01dl-2392000000-c9a7038ce5e1d2ac02ba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 20V, Positive-QTOF	splash10-01b9-5390000000-25b2d0341c1e5816a7f0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 40V, Positive-QTOF	splash10-0a4l-9430000000-23e3b1e9c96c5c37e954	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 10V, Negative-QTOF	splash10-00di-3931000000-976793c126fa75f825b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 20V, Negative-QTOF	splash10-05tf-7930000000-b6299ea4528ae8918628	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 40V, Negative-QTOF	splash10-0006-9210000000-74586dae3c499ae4f5a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 10V, Positive-QTOF	splash10-000x-0195000000-1c764f1c48cce440400c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 20V, Positive-QTOF	splash10-05x3-1391000000-77097cfbdec6540201ef	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 40V, Positive-QTOF	splash10-08fr-3890000000-4ffd41b31517867df3dc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 10V, Negative-QTOF	splash10-000i-0279000000-e86b3f4eae8b63b87e74	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 20V, Negative-QTOF	splash10-03kc-6592000000-5f82f0345e9bce5cac54	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefacetrile 40V, Negative-QTOF	splash10-05mo-9120000000-2119ddd7cb36630238c4	2021-10-11	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

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01414	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01414	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01414

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

82675

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefacetrile

METLIN ID

Not Available

PubChem Compound

91562

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Not Available

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172 ]
Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [PubMed:15618660 ]

Showing metabocard for Cefacetrile (HMDB0015484)

MOL for HMDB0015484 (Cefacetrile)

3D MOL for HMDB0015484 (Cefacetrile)

3D SDF for HMDB0015484 (Cefacetrile)

3D-SDF for HMDB0015484 (Cefacetrile)

PDB for HMDB0015484 (Cefacetrile)

3D PDB for HMDB0015484 (Cefacetrile)

SMILES for HMDB0015484 (Cefacetrile)

INCHI for HMDB0015484 (Cefacetrile)

Structure for HMDB0015484 (Cefacetrile)

3D Structure for HMDB0015484 (Cefacetrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References