NP-MRD: Showing NP-Card for 7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin (NP0031185)

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Record Information

Version

2.0

Created at

2021-06-19 22:20:11 UTC

Updated at

2021-06-29 23:59:37 UTC

NP-MRD ID

NP0031185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin

Provided By

JEOL Database JEOL Logo

Description

7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin is found in Staphylococcus aureus (MRSA). It was first documented in 2005 (Lopez, M. A., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100203D          

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M  END

     RDKit          3D

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  Mrv1652306202100203D          

 49 51  0  0  0  0            999 V2000
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 16 15  1  0  0  0  0
  8 10  1  0  0  0  0
 15 14  1  0  0  0  0
  8  9  2  0  0  0  0
 20 18  2  0  0  0  0
  2  3  2  0  0  0  0
 16 17  2  0  0  0  0
 21 22  2  0  0  0  0
 27 14  1  0  0  0  0
 22 23  1  0  0  0  0
 27 28  1  0  0  0  0
 23 24  2  0  0  0  0
 11  7  1  0  0  0  0
 24 25  1  0  0  0  0
  7  6  2  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
  6 29  1  0  0  0  0
 18 19  1  0  0  0  0
 20 41  1  0  0  0  0
 15 37  1  0  0  0  0
 14 36  1  0  0  0  0
 27 47  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 10 35  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
 24 44  1  0  0  0  0
 25 45  1  0  0  0  0
 26 46  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])S[C@@]2([H])N1C(=O)[C@]2([H])N([H])C(=O)C(=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O6S/c1-11(8-13-6-4-3-5-7-13)17(24)21-15-18(25)22-16(20(26)27)14(9-28-12(2)23)10-29-19(15)22/h3-8,15,19H,9-10H2,1-2H3,(H,21,24)(H,26,27)/b11-8+/t15-,19+/m0/s1

> <INCHI_KEY>
SLSHXRMOTFYIDI-DPFKQAOISA-N

> <FORMULA>
C20H20N2O6S

> <MOLECULAR_WEIGHT>
416.45

> <EXACT_MASS>
416.104207546

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
42.70510945277954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
1.0240341776666666

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.014032149735502

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.726365215527241

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5673564810095842

> <JCHEM_POLAR_SURFACE_AREA>
113.00999999999999

> <JCHEM_REFRACTIVITY>
106.95550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7S)-3-[(acetyloxy)methyl]-7-[(2E)-2-methyl-3-phenylprop-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -5.1879    4.0544   -5.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9613    3.2503   -4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    3.4326   -4.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625    2.2938   -3.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8187    1.4778   -2.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8398    0.4062   -2.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005    0.1722   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625    0.8924   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3611    1.0282    0.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571    1.4457    0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -0.7699   -0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -1.4544    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -1.3979    1.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -2.3600   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -2.3774   -0.2791 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -2.4510   -1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -2.5153   -2.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545   -2.5040   -0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -3.5538   -1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587   -1.6176    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -1.5322    1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861   -1.0598    0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5170   -0.9752    1.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255   -1.3578    2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040   -1.8234    3.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -1.9089    2.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6543   -1.3635   -1.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -2.0437   -3.2116 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014   -0.4092   -3.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    4.8223   -5.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    3.4052   -6.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458    4.5469   -4.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7042    1.0022   -3.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1322    2.1278   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7941    1.8204    1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -3.3813   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -2.3950    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -3.7141   -0.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361   -4.5161   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685   -3.2760   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.8711    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -0.7542   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3906   -0.6095    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5843   -1.2914    2.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891   -2.1199    4.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.2745    2.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.6665   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    0.1507   -4.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1014   -0.5979   -4.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 21 20  1  0
  6  5  1  0
 18 16  1  0
  5  4  1  0
 14 12  1  0
  4  2  1  0
 12 11  1  0
  2  1  1  0
 27 11  1  0
 12 13  2  0
  7  8  1  0
 16 15  1  0
  8 10  1  0
 15 14  1  0
  8  9  2  0
 20 18  2  0
  2  3  2  0
 16 17  2  0
 21 22  2  0
 27 14  1  0
 22 23  1  0
 27 28  1  0
 23 24  2  0
 11  7  1  0
 24 25  1  0
  7  6  2  0
 25 26  2  0
 26 21  1  0
  6 29  1  0
 18 19  1  0
 20 41  1  0
 15 37  1  0
 14 36  1  0
 27 47  1  0
 29 48  1  0
 29 49  1  0
  5 33  1  0
  5 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 10 35  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.188   4.054  -5.482  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.961   3.250  -4.483  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.138   3.433  -4.208  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.162   2.294  -3.936  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.819   1.478  -2.954  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.840   0.406  -2.523  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.500   0.172  -1.234  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.162   0.892  -0.114  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.361   1.028   0.049  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.257   1.446   0.712  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.577  -0.770  -0.917  0.00  0.00           N+0
HETATM   12  C   UNK     0      -3.185  -1.454   0.172  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.482  -1.398   1.342  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.265  -2.360  -0.720  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.841  -2.377  -0.279  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.201  -2.451  -1.166  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.054  -2.515  -2.380  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.555  -2.504  -0.542  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.457  -3.554  -1.118  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.859  -1.618   0.425  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.158  -1.532   1.095  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.286  -1.060   0.414  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.517  -0.975   1.068  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.625  -1.358   2.404  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.504  -1.823   3.089  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.272  -1.909   2.438  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.654  -1.363  -1.859  0.00  0.00           C+0
HETATM   28  S   UNK     0      -3.651  -2.044  -3.212  0.00  0.00           S+0
HETATM   29  C   UNK     0      -4.301  -0.409  -3.688  0.00  0.00           C+0
HETATM   30  H   UNK     0      -5.838   4.822  -5.911  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.837   3.405  -6.288  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.346   4.547  -4.990  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.704   1.002  -3.394  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.132   2.128  -2.134  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.794   1.820   1.440  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.652  -3.381  -0.818  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.637  -2.395   0.715  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.358  -3.714  -0.519  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.936  -4.516  -1.169  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.769  -3.276  -2.130  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.141  -0.871   0.758  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.214  -0.754  -0.627  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.391  -0.610   0.534  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.584  -1.291   2.912  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.589  -2.120   4.131  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.407  -2.275   2.985  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.866  -0.667  -2.166  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.511   0.151  -4.200  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.101  -0.598  -4.412  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   33   34                                             
CONECT    6    5    7   29                                                  
CONECT    7    8   11    6                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   35                                                       
CONECT   11   12   27    7                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   27   36                                             
CONECT   15   16   14   37                                                  
CONECT   16   18   15   17                                                  
CONECT   17   16                                                            
CONECT   18   16   20   19                                                  
CONECT   19   18   38   39   40                                             
CONECT   20   21   18   41                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   42                                                  
CONECT   23   22   24   43                                                  
CONECT   24   23   25   44                                                  
CONECT   25   24   26   45                                                  
CONECT   26   25   21   46                                                  
CONECT   27   11   14   28   47                                             
CONECT   28   29   27                                                       
CONECT   29   28    6   48   49                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35   10                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   29                                                            
CONECT   49   29                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

RDKit          3D

49 51  0  0  0  0  0  0  0  0999 V2000
   -5.1879    4.0544   -5.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9613    3.2503   -4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    3.4326   -4.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625    2.2938   -3.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8187    1.4778   -2.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8398    0.4062   -2.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005    0.1722   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625    0.8924   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3611    1.0282    0.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571    1.4457    0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -0.7699   -0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -1.4544    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -1.3979    1.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -2.3600   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -2.3774   -0.2791 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -2.4510   -1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -2.5153   -2.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545   -2.5040   -0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573   -3.5538   -1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587   -1.6176    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -1.5322    1.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861   -1.0598    0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5170   -0.9752    1.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255   -1.3578    2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040   -1.8234    3.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -1.9089    2.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6543   -1.3635   -1.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -2.0437   -3.2116 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3014   -0.4092   -3.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    4.8223   -5.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    3.4052   -6.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458    4.5469   -4.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7042    1.0022   -3.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1322    2.1278   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7941    1.8204    1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -3.3813   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -2.3950    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -3.7141   -0.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361   -4.5161   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685   -3.2760   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.8711    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -0.7542   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3906   -0.6095    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5843   -1.2914    2.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891   -2.1199    4.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.2745    2.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.6665   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    0.1507   -4.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1014   -0.5979   -4.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 21 20  1  0
  6  5  1  0
 18 16  1  0
  5  4  1  0
 14 12  1  0
  4  2  1  0
 12 11  1  0
  2  1  1  0
 27 11  1  0
 12 13  2  0
  7  8  1  0
 16 15  1  0
  8 10  1  0
 15 14  1  0
  8  9  2  0
 20 18  2  0
  2  3  2  0
 16 17  2  0
 21 22  2  0
 27 14  1  0
 22 23  1  0
 27 28  1  0
 23 24  2  0
 11  7  1  0
 24 25  1  0
  7  6  2  0
 25 26  2  0
 26 21  1  0
  6 29  1  0
 18 19  1  0
 20 41  1  0
 15 37  1  0
 14 36  1  0
 27 47  1  0
 29 48  1  0
 29 49  1  0
  5 33  1  0
  5 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 10 35  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀N₂O₆S

Average Mass

416.4500 Da

Monoisotopic Mass

416.10421 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])S[C@@]2([H])N1C(=O)[C@]2([H])N([H])C(=O)C(=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C20H20N2O6S/c1-11(8-13-6-4-3-5-7-13)17(24)21-15-18(25)22-16(20(26)27)14(9-28-12(2)23)10-29-19(15)22/h3-8,15,19H,9-10H2,1-2H3,(H,21,24)(H,26,27)/b11-8+/t15-,19+/m0/s1

InChI Key

SLSHXRMOTFYIDI-DPFKQAOISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Staphylococcus aureus	JEOL database	Lopez, M. A., et al, Magn. Reson. Chem. 43, 261 (2005)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.3	ALOGPS
logP	1.02	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-0.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.01 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.96 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Lopez, M. A., et al. (2005). Lopez, M. A., et al, Magn. Reson. Chem. 43, 261 (2005). Mag. Reson. Chem..

Showing NP-Card for 7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin (NP0031185)

MOL for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

3D MOL for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

3D SDF for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

3D-SDF for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

PDB for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

3D PDB for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

SMILES for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

INCHI for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

Structure for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)

3D Structure for NP0031185 (7beta-(alpha-methylcinnamoyl)amino-3-acetoxymethyl-cephalosporin)