NP-MRD: Showing NP-Card for (6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0206384)

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Record Information

Version

2.0

Created at

2022-09-05 02:36:46 UTC

Updated at

2022-09-05 02:36:46 UTC

NP-MRD ID

NP0206384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

Cephamycin A belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position. Based on a literature review very few articles have been published on Cephamycin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204362D          

 44 46  0  0  1  0            999 V2000
   -5.5539   10.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    9.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5539    9.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7914    8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2039    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4414    8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2664    8.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6789    9.0158    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0914    9.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3934    8.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9645    9.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289    9.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2039    9.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289    9.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    9.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    8.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4914    8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8414    6.8724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8250    5.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7474    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    4.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9520    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    6.1579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0789    6.1579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4914    6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
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 10 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 15  1  0  0  0  0
  3 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
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 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  4  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 28 40  1  6  0  0  0
 40 41  1  0  0  0  0
 28 42  1  0  0  0  0
 42 25  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 20 44  1  0  0  0  0
M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
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    6.1931    1.7526   -0.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2644   -0.8497   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8044   -2.0043   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2653    3.2746    1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647    4.3091    1.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1232   -3.7478   -0.3169 C   0  0  1  0  0  0  0  0  0  0  0  0
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 39 67  1  0
 24 56  1  0
M  END


  Mrv1652309052204362D          

 44 46  0  0  1  0            999 V2000
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   -1.5395    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    4.5079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329    5.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    4.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    6.1579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0789    6.1579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4914    6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 15  1  0  0  0  0
  3 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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  4  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 28 40  1  6  0  0  0
 40 41  1  0  0  0  0
 28 42  1  0  0  0  0
 42 25  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 20 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C(=C/C1=CC=C(OS(O)(=O)=O)C=C1)C(=O)OCC1=C(N2[C@H](SC1)[C@](OC)(N=C(O)CCC[C@@H](N)C(O)=O)C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H29N3O14S2/c1-39-17(10-13-6-8-15(9-7-13)42-44(36,37)38)22(34)41-11-14-12-43-24-25(40-2,23(35)28(24)19(14)21(32)33)27-18(29)5-3-4-16(26)20(30)31/h6-10,16,24H,3-5,11-12,26H2,1-2H3,(H,27,29)(H,30,31)(H,32,33)(H,36,37,38)/b17-10-/t16-,24-,25+/m1/s1

> <INCHI_KEY>
AGMXVTRKEHGDRH-MYWSHXOVSA-N

> <FORMULA>
C25H29N3O14S2

> <MOLECULAR_WEIGHT>
659.63

> <EXACT_MASS>
659.109094974

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
63.27869248945457

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7S)-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2Z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_LOGP>
-0.18388651508291273

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.6069937944495538

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.2972978339138317

> <JCHEM_PKA_STRONGEST_BASIC>
9.527051249126512

> <JCHEM_POLAR_SURFACE_AREA>
261.88

> <JCHEM_REFRACTIVITY>
151.34999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7S)-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2Z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.367  19.497   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -11.137  18.163   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -10.367  16.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.137  15.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.677  15.496   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.447  14.162   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.987  14.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -15.757  15.496   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -17.297  15.496   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0     -18.067  16.829   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0     -18.837  18.163   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -19.401  16.059   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0     -16.734  17.599   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -14.987  16.829   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.447  16.829   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.827  16.829   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.057  18.163   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.057  15.496   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.517  15.496   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.747  14.162   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.207  14.162   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.437  15.496   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.897  15.496   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.207  16.829   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0      -3.437  12.828   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -2.104  12.058   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.616  12.457   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.874  10.725   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -1.540   9.955   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.540   8.415   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.874   7.645   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.206   7.645   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.127   8.415   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.461   7.645   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.795   8.415   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       3.795   9.955   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       5.128   7.645   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.462   8.415   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.128   6.105   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.644   9.391   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.184   9.391   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.207  11.495   0.000  0.00  0.00           C+0
HETATM   43  S   UNK     0      -5.747  11.495   0.000  0.00  0.00           S+0
HETATM   44  C   UNK     0      -6.517  12.828   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    8   15                                                       
CONECT   15   14    5                                                       
CONECT   16    3   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   44                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   42                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   40   42                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   28   41                                                       
CONECT   41   40                                                            
CONECT   42   28   25   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   20                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₉N₃O₁₄S₂

Average Mass

659.6300 Da

Monoisotopic Mass

659.10909 Da

IUPAC Name

(6R,7S)-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2Z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

(6R,7S)-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2Z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO\C(=C/C1=CC=C(OS(O)(=O)=O)C=C1)C(=O)OCC1=C(N2[C@H](SC1)[C@](OC)(N=C(O)CCC[C@@H](N)C(O)=O)C2=O)C(O)=O

InChI Identifier

InChI=1S/C25H29N3O14S2/c1-39-17(10-13-6-8-15(9-7-13)42-44(36,37)38)22(34)41-11-14-12-43-24-25(40-2,23(35)28(24)19(14)21(32)33)27-18(29)5-3-4-16(26)20(30)31/h6-10,16,24H,3-5,11-12,26H2,1-2H3,(H,27,29)(H,30,31)(H,32,33)(H,36,37,38)/b17-10-/t16-,24-,25+/m1/s1

InChI Key

AGMXVTRKEHGDRH-MYWSHXOVSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Cephamycin
N-acyl-alpha amino acid or derivatives
Cinnamic acid or derivatives
Enol-phenylpyruvate
Cinnamic acid ester
Phenylsulfate
Alpha-amino acid
Alpha-amino acid or derivatives
Arylsulfate
D-alpha-amino acid
Tricarboxylic acid or derivatives
Phenoxy compound
Fatty acid ester
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Fatty amide
N-acyl-amine
Meta-thiazine
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Tertiary carboxylic acid amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxylic acid ester
Carboxamide group
Azetidine
Amino acid
Azacycle
Dialkylthioether
Hemithioaminal
Carboxylic acid derivative
Thioether
Carboxylic acid
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.18	ChemAxon
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	261.88 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	151.35 m³·mol⁻¹	ChemAxon
Polarizability	63.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16735728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20054862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0206384)

MOL for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0206384 ((6r,7s)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-3-({[(2z)-2-methoxy-3-[4-(sulfooxy)phenyl]prop-2-enoyl]oxy}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)