MiMeDB: Showing metabocard for Cephalosporin C (MMDBc0009798)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:12:48 UTC

Update Date

2022-08-31 06:30:45 UTC

Metabolite ID

MMDBc0009798

Metabolite Identification

Common Name

Cephalosporin C

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. 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 is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

  Mrv1533004231523552D          

 28 29  0  0  0  0            999 V2000
   -5.3501    2.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    3.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9803    4.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    3.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3865    3.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    3.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    3.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094    3.7447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792    2.3645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761    2.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    2.7489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    3.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6589    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879    3.9864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168    3.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023    1.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364    5.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167    4.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

  Mrv1533004231523552D          

 28 29  0  0  0  0            999 V2000
   -5.3501    2.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    3.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9803    4.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    3.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3865    3.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    3.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    3.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094    3.7447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792    2.3645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761    2.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    2.7489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300    3.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6589    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879    3.9864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168    3.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023    1.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364    5.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167    4.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009798

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C16H21N3O8S

> <MOLECULAR_WEIGHT>
415.42

> <EXACT_MASS>
415.104935822

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.232348179110915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(acetyloxy)methyl]-7-(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>
95.42719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cephalosporin C

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -9.987   4.919   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.898   6.008   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -9.297   7.496   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -7.410   5.609   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.322   6.698   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.834   6.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.745   7.389   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.258   6.990   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.859   5.503   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -2.948   4.414   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0      -4.435   4.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.371   5.901   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.962   5.131   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.296   5.901   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.296   7.441   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.630   5.131   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.963   5.901   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.297   5.131   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.631   5.901   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       7.631   7.441   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.964   5.131   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.298   5.901   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.964   3.591   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.770   7.389   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000   8.722   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.144   8.876   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.055   9.965   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.631   9.275   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12    8   25                                                  
CONECT   25   24                                                            
CONECT   26    7   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

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

Molecular Formula

C₁₆H₂₁N₃O₈S

Average Mass

415.42

Monoisotopic Mass

415.104935822

IUPAC Name

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

Traditional Name

cephalosporin C

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

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Cephalosporin C (MMDBc0009798)

MOL for #<Metabolite:0x00007fd5f9606ec8>

3D MOL for #<Metabolite:0x00007fd5f9606ec8>

3D SDF for #<Metabolite:0x00007fd5f9606ec8>

3D-SDF for #<Metabolite:0x00007fd5f9606ec8>

PDB for #<Metabolite:0x00007fd5f9606ec8>

3D PDB for #<Metabolite:0x00007fd5f9606ec8>

SMILES for #<Metabolite:0x00007fd5f9606ec8>

INCHI for #<Metabolite:0x00007fd5f9606ec8>

Structure for #<Metabolite:0x00007fd5f9606ec8>

3D Structure for #<Metabolite:0x00007fd5f9606ec8>