NP-MRD: Showing NP-Card for Cephalosporin C (NP0004786)

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Record Information

Version

2.0

Created at

2020-12-09 02:12:03 UTC

Updated at

2021-07-15 16:50:09 UTC

NP-MRD ID

NP0004786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cephalosporin C

Provided By

NPAtlas

Description

3-[(Acetyloxy)methyl]-7-[(5-amino-5-carboxy-1-hydroxypentylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position. Cephalosporin C is found in Acremonium sp. and Penicillium chrysogenum. Based on a literature review very few articles have been published on 3-[(acetyloxy)methyl]-7-[(5-amino-5-carboxy-1-hydroxypentylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 49 50  0  0  0  0            999 V2000
    8.2422    0.9886   -1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686    0.4668   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678    0.0920   -2.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.4038   -0.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.0730   -1.4447 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4402   -0.1775   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.1498    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    0.6960    1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    0.9813    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481    0.9806    1.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8677   -0.0081    1.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314   -0.5255    2.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262   -0.8144    3.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5197   -0.7636    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8158   -0.2799    1.7905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9978   -1.0610    1.3152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1982   -1.0738   -0.1605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3664    0.3159   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5451    0.1413   -2.1712 N   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5712    0.9638   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5916    1.3352    1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    1.1844   -0.9408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.5841    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8929    0.4129   -1.3087 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -0.8077   -1.4814 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7126    1.6726   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9297    0.1259   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4896    0.4156   -2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 22 45  1  0  0  0  0
 25 46  1  0  0  0  0
 26 47  1  6  0  0  0
 28 48  1  0  0  0  0
 28 49  1  0  0  0  0
M  END

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
    8.2422    0.9886   -1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686    0.4668   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678    0.0920   -2.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6750   -0.0730   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2529   -0.8077   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  2  0
  2  4  1  0
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M  END


  Mrv1652306242121113D          

 49 50  0  0  0  0            999 V2000
    8.2422    0.9886   -1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686    0.4668   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6750   -0.0730   -1.4447 C   0  0  1  0  0  0  0  0  0  0  0  0
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 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28  6  1  0  0  0  0
 26 11  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
 10 34  1  0  0  0  0
 14 35  1  6  0  0  0
 15 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 21 43  1  6  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 25 46  1  0  0  0  0
 26 47  1  6  0  0  0
 28 48  1  0  0  0  0
 28 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004786

> <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([H])([H])C([H])([H])C([H])([H])[C@@]([H])(N([H])[H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14+/m1/s1

> <INCHI_KEY>
HOKIDJSKDBPKTQ-UHFFFAOYSA-N

> <FORMULA>
C16H21N3O8S

> <MOLECULAR_WEIGHT>
415.42

> <EXACT_MASS>
415.104935822

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.63649873772282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-4.3573375949766895

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6875050748975147

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8375042564087951

> <JCHEM_PKA_STRONGEST_BASIC>
9.224805327069886

> <JCHEM_POLAR_SURFACE_AREA>
176.32999999999998

> <JCHEM_REFRACTIVITY>
95.42719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
    8.2422    0.9886   -1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686    0.4668   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678    0.0920   -2.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.4038   -0.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.0730   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4402   -0.1775   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.1498    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    0.6960    1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    0.9813    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481    0.9806    1.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8677   -0.0081    1.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314   -0.5255    2.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262   -0.8144    3.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -0.5530    1.1459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3425   -0.0790    1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -0.7636    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -1.7766    0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158   -0.2799    1.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9978   -1.0610    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982   -1.0738   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3664    0.3159   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5451    0.1413   -2.1712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5712    0.9638   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5916    1.3352    1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    1.1844   -0.9408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.5841    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8929    0.4129   -1.3087 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -0.8077   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126    1.6726   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0998    1.4925   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9297    0.1259   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4896    0.4156   -2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -1.1535   -1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3290    0.7386    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530   -1.4571    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.7628    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8430   -0.2862    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9342    0.7679    1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9076   -0.6647    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -2.1438    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.6141   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1193   -1.6821   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402    0.8855   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4882    1.1089   -2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4761   -0.2995   -2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2267    0.4137   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428    1.5736    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.7675   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.8653   -2.5309 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  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 14 26  1  0
 26 27  1  0
 27 28  1  0
 28  6  1  0
 26 11  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  0
 14 35  1  6
 15 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 25 46  1  0
 26 47  1  6
 28 48  1  0
 28 49  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       8.242   0.989  -1.168  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.969   0.467  -1.724  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.968   0.092  -2.924  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.833   0.404  -0.932  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.675  -0.073  -1.445  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.440  -0.178  -0.702  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.210   0.150   0.543  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.239   0.696   1.412  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.931   0.981   2.646  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.548   0.981   1.151  0.00  0.00           O+0
HETATM   11  N   UNK     0       1.868  -0.008   1.111  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.031  -0.526   2.121  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.226  -0.814   3.328  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.072  -0.553   1.146  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.343  -0.079   1.634  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.520  -0.764   1.292  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.466  -1.777   0.569  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.816  -0.280   1.791  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.998  -1.061   1.315  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.198  -1.074  -0.161  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.366   0.316  -0.721  0.00  0.00           C+0
HETATM   22  N   UNK     0      -5.545   0.141  -2.171  0.00  0.00           N+0
HETATM   23  C   UNK     0      -6.571   0.964  -0.166  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.592   1.335   1.026  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.721   1.184  -0.941  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.682   0.584   0.491  0.00  0.00           C+0
HETATM   27  S   UNK     0       0.893   0.413  -1.309  0.00  0.00           S+0
HETATM   28  C   UNK     0       2.253  -0.808  -1.481  0.00  0.00           C+0
HETATM   29  H   UNK     0       8.713   1.673  -1.921  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.100   1.492  -0.191  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.930   0.126  -1.069  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.490   0.416  -2.474  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.896  -1.153  -1.806  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.329   0.739   1.748  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.153  -1.457   0.516  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.374   0.763   2.233  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.843  -0.286   2.906  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.934   0.768   1.444  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.908  -0.665   1.809  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.845  -2.144   1.621  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.379  -1.614  -0.671  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.119  -1.682  -0.356  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.440   0.886  -0.572  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.488   1.109  -2.586  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.476  -0.300  -2.374  0.00  0.00           H+0
HETATM   46  H   UNK     0      -8.227   0.414  -1.321  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.443   1.574   0.865  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.986  -1.768  -1.003  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.502  -0.865  -2.531  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32   33                                             
CONECT    6    5    7   28                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   34                                                       
CONECT   11    7   12   26                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   26   35                                             
CONECT   15   14   16   36                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   37   38                                             
CONECT   19   18   20   39   40                                             
CONECT   20   19   21   41   42                                             
CONECT   21   20   22   23   43                                             
CONECT   22   21   44   45                                                  
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   46                                                       
CONECT   26   14   27   11   47                                             
CONECT   27   26   28                                                       
CONECT   28   27    6   48   49                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34   10                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   25                                                            
CONECT   47   26                                                            
CONECT   48   28                                                            
CONECT   49   28                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  100    0
END

RDKit          3D

49 50  0  0  0  0  0  0  0  0999 V2000
    8.2422    0.9886   -1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686    0.4668   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678    0.0920   -2.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.4038   -0.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.0730   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4402   -0.1775   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.1498    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    0.6960    1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    0.9813    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481    0.9806    1.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8677   -0.0081    1.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314   -0.5255    2.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262   -0.8144    3.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -0.5530    1.1459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3425   -0.0790    1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -0.7636    1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -1.7766    0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158   -0.2799    1.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9978   -1.0610    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982   -1.0738   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3664    0.3159   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5451    0.1413   -2.1712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5712    0.9638   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5916    1.3352    1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    1.1844   -0.9408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.5841    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8929    0.4129   -1.3087 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -0.8077   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126    1.6726   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0998    1.4925   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9297    0.1259   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4896    0.4156   -2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -1.1535   -1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3290    0.7386    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530   -1.4571    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.7628    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8430   -0.2862    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9342    0.7679    1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9076   -0.6647    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -2.1438    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -1.6141   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1193   -1.6821   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4402    0.8855   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4882    1.1089   -2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4761   -0.2995   -2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2267    0.4137   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428    1.5736    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.7675   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.8653   -2.5309 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  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 14 26  1  0
 26 27  1  0
 27 28  1  0
 28  6  1  0
 26 11  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  0
 14 35  1  6
 15 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 25 46  1  0
 26 47  1  6
 28 48  1  0
 28 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-[(Acetyloxy)methyl]-7-[(5-amino-5-carboxy-1-hydroxypentylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator

Chemical Formula

C₁₆H₂₁N₃O₈S

Average Mass

415.4200 Da

Monoisotopic Mass

415.10494 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C(N2C(SC1)C(NC(=O)CCCC(N)C(O)=O)C2=O)C(O)=O

InChI Identifier

InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)

InChI Key

HOKIDJSKDBPKTQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acremonium sp.	NPAtlas	13681080
Penicillium chrysogenum	LOTUS Database	35616633

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
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Meta-thiazine
Fatty amide
N-acyl-amine
Fatty acyl
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Carboxamide group
Carboxylic acid ester
Amino acid
Secondary carboxylic acid amide
Dialkylthioether
Hemithioaminal
Thioether
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Primary amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-2.2	ALOGPS
logP	-4.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	176.33 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	95.43 m³·mol⁻¹	ChemAxon
Polarizability	40.64 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

External Links

NPAtlas ID

NPA009329

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2568

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2669

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cephalosporin C (NP0004786)

MOL for NP0004786 (Cephalosporin C)

3D MOL for NP0004786 (Cephalosporin C)

3D SDF for NP0004786 (Cephalosporin C)

3D-SDF for NP0004786 (Cephalosporin C)

PDB for NP0004786 (Cephalosporin C)

3D PDB for NP0004786 (Cephalosporin C)

SMILES for NP0004786 (Cephalosporin C)

INCHI for NP0004786 (Cephalosporin C)

Structure for NP0004786 (Cephalosporin C)

3D Structure for NP0004786 (Cephalosporin C)