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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (4) Show 5 proteins XML

enzymes (1)transporters (4) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015428

Secondary Accession Numbers

HMDB15428

Metabolite Identification

Common Name

Cefradine

Description

Cefradine is only found in individuals that have used or taken this drug. It is a semi-synthetic cephalosporin antibiotic.Cefradine is a first generation cephalosporin antibiotic with a spectrum of activity similar to Cefalexin. Cefradine, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Cefradine interferes with an autolysin inhibitor.

Structure

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

HMDB0015428
     RDKit          3D
Cefradine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.3339    2.4306   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1758    1.5023   -1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    0.6067   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715    0.5746    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574    1.3047    0.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -0.3767    1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237   -0.3170   -0.2586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291   -1.0905    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -1.4573    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -1.3798   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0391   -0.5610   -0.6242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.0634   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -2.2862   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -0.1678   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0212    1.1859   -0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942   -0.5259    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -1.5491    1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.8172    2.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7549   -1.5261    1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688   -0.4907    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.3690    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -0.8281   -1.4619 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8046    0.6780   -2.3828 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.6776   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    3.1006   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237    3.1109   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142    1.9414   -1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0006    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708   -2.4516   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.4542   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.1678   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    1.3184    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    1.8455   -0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -2.1857    1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050   -2.8893    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.1696    3.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6390   -2.1232    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8067   -0.2566    0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447    1.0883    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.9525   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -1.5420   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097    1.3327   -3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    2.7494   -2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 22  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  6
 11 30  1  0
 14 31  1  6
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  6
 24 42  1  0
 24 43  1  0
M  END

1333
  Mrv0541 02231215232D          

 25 27  0  0  1  0            999 V2000
    3.0790   -0.8460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074    0.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2199   -0.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.3915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -1.0214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717   -2.1906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6253   -0.4369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6253    0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048   -0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5869   -1.3942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3842   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5994   -0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9664   -1.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7637   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3967   -0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9789   -0.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.0713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2 11  2  0  0  0  0
  3 15  2  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
 10  7  1  1  0  0  0
  7 15  1  0  0  0  0
 16  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 25  1  6  0  0  0
 10 11  1  0  0  0  0
 12 14  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015428

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

> <INCHI_KEY>
RDLPVSKMFDYCOR-UEKVPHQBSA-N

> <FORMULA>
C16H19N3O4S

> <MOLECULAR_WEIGHT>
349.405

> <EXACT_MASS>
349.109626801

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.18662935650122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
-2.4468313670826145

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.994637340673762

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.464879253810305

> <JCHEM_PKA_STRONGEST_BASIC>
7.595405062327526

> <JCHEM_POLAR_SURFACE_AREA>
112.72999999999999

> <JCHEM_REFRACTIVITY>
91.99560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cefradine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015428
     RDKit          3D
Cefradine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.3339    2.4306   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1758    1.5023   -1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    0.6067   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715    0.5746    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574    1.3047    0.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -0.3767    1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237   -0.3170   -0.2586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291   -1.0905    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -1.4573    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -1.3798   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0391   -0.5610   -0.6242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.0634   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -2.2862   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -0.1678   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0212    1.1859   -0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942   -0.5259    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -1.5491    1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.8172    2.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7549   -1.5261    1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688   -0.4907    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.3690    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -0.8281   -1.4619 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8046    0.6780   -2.3828 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.6776   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    3.1006   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237    3.1109   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142    1.9414   -1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0006    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708   -2.4516   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.4542   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.1678   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    1.3184    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    1.8455   -0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -2.1857    1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050   -2.8893    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.1696    3.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6390   -2.1232    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8067   -0.2566    0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447    1.0883    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.9525   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -1.5420   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097    1.3327   -3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    2.7494   -2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 22  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  6
 11 30  1  0
 14 31  1  6
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  6
 24 42  1  0
 24 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1333                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.747  -1.579   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.720   1.828   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.610  -0.024   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   3.811   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   3.811   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081   0.731   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.720  -1.907   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.894  -4.089   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.081  -0.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.634  -0.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.634   0.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   1.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -0.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.209  -1.511   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.296  -2.603   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   1.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747   3.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.784  -2.207   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.186  -0.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.871  -3.298   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.359  -2.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.674  -0.325   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.761  -1.416   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       7.397  -2.000   0.000  0.00  0.00           H+0
CONECT    1    9   13                                                       
CONECT    2   11                                                            
CONECT    3   15                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6    9   11   12                                                  
CONECT    7   10   15                                                       
CONECT    8   16                                                            
CONECT    9    1    6   10   25                                             
CONECT   10    7    9   11                                                  
CONECT   11    2    6   10                                                  
CONECT   12    6   14   18                                                  
CONECT   13    1   14                                                       
CONECT   14   12   13   17                                                  
CONECT   15    3    7   16                                                  
CONECT   16    8   15   19                                                  
CONECT   17   14                                                            
CONECT   18    4    5   12                                                  
CONECT   19   16   20   21                                                  
CONECT   20   19   23                                                       
CONECT   21   19   22                                                       
CONECT   22   21   24                                                       
CONECT   23   20   24                                                       
CONECT   24   22   23                                                       
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0015428
HETATM    1  C1  UNL     1       5.334   2.431  -1.137  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.176   1.502  -1.211  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.003   0.607  -0.256  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.972   0.575   0.840  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.957   1.305   0.978  1.00  0.00           O  
HETATM    6  O2  UNL     1       4.789  -0.377   1.861  1.00  0.00           O  
HETATM    7  N1  UNL     1       2.924  -0.317  -0.259  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.029  -1.090   0.476  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.937  -1.457   1.674  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.132  -1.380  -0.688  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.039  -0.561  -0.624  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.348  -1.063  -0.808  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.579  -2.286  -1.043  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.503  -0.168  -0.729  1.00  0.00           C  
HETATM   15  N3  UNL     1      -2.021   1.186  -0.494  1.00  0.00           N  
HETATM   16  C9  UNL     1      -3.494  -0.526   0.314  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.392  -1.549   1.145  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.456  -1.817   2.161  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.755  -1.526   1.508  1.00  0.00           C  
HETATM   20  C13 UNL     1      -5.869  -0.491   0.680  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.701   0.369   0.410  1.00  0.00           C  
HETATM   22  C15 UNL     1       2.299  -0.828  -1.462  1.00  0.00           C  
HETATM   23  S1  UNL     1       1.805   0.678  -2.383  1.00  0.00           S  
HETATM   24  C16 UNL     1       3.292   1.678  -2.391  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.311   3.101  -0.253  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.324   3.111  -2.031  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.314   1.941  -1.170  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.519  -0.001   2.763  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.971  -2.452  -0.891  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.071   0.454  -0.434  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.058  -0.168  -1.709  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.961   1.318   0.555  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.781   1.846  -0.813  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.524  -2.186   1.075  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.405  -2.889   2.463  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.321  -1.170   3.029  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.639  -2.123   1.671  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.807  -0.257   0.190  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.545   1.088   1.249  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.852   0.952  -0.509  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.889  -1.542  -2.062  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.910   1.333  -3.273  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.093   2.749  -2.603  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   24
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    6   28
CONECT    7    8   22
CONECT    8    9    9   10
CONECT   10   11   22   29
CONECT   11   12   30
CONECT   12   13   13   14
CONECT   14   15   16   31
CONECT   15   32   33
CONECT   16   17   17   21
CONECT   17   18   34
CONECT   18   19   35   36
CONECT   19   20   20   37
CONECT   20   21   38
CONECT   21   39   40
CONECT   22   23   41
CONECT   23   24
CONECT   24   42   43
END

HMDB0015428
     RDKit          3D
Cefradine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.3339    2.4306   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1758    1.5023   -1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    0.6067   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715    0.5746    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574    1.3047    0.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -0.3767    1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237   -0.3170   -0.2586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291   -1.0905    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -1.4573    1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -1.3798   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0391   -0.5610   -0.6242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -1.0634   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -2.2862   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -0.1678   -0.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0212    1.1859   -0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942   -0.5259    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -1.5491    1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.8172    2.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7549   -1.5261    1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688   -0.4907    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    0.3690    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -0.8281   -1.4619 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8046    0.6780   -2.3828 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    1.6776   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    3.1006   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237    3.1109   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142    1.9414   -1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0006    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708   -2.4516   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.4542   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.1678   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    1.3184    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    1.8455   -0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -2.1857    1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050   -2.8893    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.1696    3.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6390   -2.1232    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8067   -0.2566    0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447    1.0883    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520    0.9525   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886   -1.5420   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097    1.3327   -3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    2.7494   -2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 22  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  6
 11 30  1  0
 14 31  1  6
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  6
 24 42  1  0
 24 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(6R,7R)-7-((R)-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid	ChEBI
(6R,7R)-7-{[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
7-(D-2-Amino-2-(1,4-cyclohexadienyl)acetamide)desacetoxycephalosporanicacid	ChEBI
Anspor	ChEBI
CED	ChEBI
Cefradina	ChEBI
Cefradinum	ChEBI
Cephradin	ChEBI
Eskacef	ChEBI
Sefril	ChEBI
Velosef	ChEBI
(6R,7R)-7-((R)-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-{[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Cephradine	HMDB
Dexef	HMDB
Galen brand OF cephradine	HMDB
Septa brand OF cephradine	HMDB
Alpharma brand OF cephradine	HMDB
Cephradine dihydrate	HMDB
Cephradine, non-stoichiometric hydrate	HMDB
Dexo brand OF cephradine	HMDB
Kelsef	HMDB
Septacef	HMDB
Bristol-myers squibb brand OF cefradine	HMDB
Maxisporin	HMDB
Nicef	HMDB
Non-stoichiometric hydrate cephradine	HMDB
Reig jofre brand OF cephradine	HMDB
Zeefra gé	HMDB
Bouchara brand OF cephradine	HMDB
Cephradine, NON stoichiometric hydrate	HMDB
Dihydrate, cephradine	HMDB
Squibb brand OF cephradine	HMDB
Velocef	HMDB
Yamanouchi brand OF cephradine	HMDB
Cefradine	ChEBI

Chemical Formula

C₁₆H₁₉N₃O₄S

Average Molecular Weight

349.405

Monoisotopic Molecular Weight

349.109626801

IUPAC Name

(6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefradine

CAS Registry Number

38821-53-3

SMILES

[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O

InChI Identifier

InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

InChI Key

RDLPVSKMFDYCOR-UEKVPHQBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Cephem
Meta-thiazine
Beta-lactam
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Amino acid
Lactam
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Dialkylthioether
Thioether
Hemithioaminal
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organic nitrogen compound
Organic oxide
Amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3547 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015428)
Membrane (HMDB: HMDB0015428)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.78 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	0.7	ALOGPS
logP	-2.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92 m³·mol⁻¹	ChemAxon
Polarizability	33.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.795	31661259
DarkChem	[M-H]-	173.55	31661259
DeepCCS	[M-2H]-	214.748	30932474
DeepCCS	[M+Na]+	189.908	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.7	32859911
AllCCS	[M+NH4]+	183.0	32859911
AllCCS	[M+Na]+	183.8	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cefradine	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O	4022.1	Standard polar	33892256
Cefradine	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O	2684.7	Standard non polar	33892256
Cefradine	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O	3161.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cefradine,1TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1	2956.0	Semi standard non polar	33892256
Cefradine,1TMS,isomer #2	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[C@H]2SC1	3029.3	Semi standard non polar	33892256
Cefradine,1TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2882.8	Semi standard non polar	33892256
Cefradine,2TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[C@H]2SC1	2957.8	Semi standard non polar	33892256
Cefradine,2TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[C@H]2SC1	2719.9	Standard non polar	33892256
Cefradine,2TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[C@H]2SC1	4349.8	Standard polar	33892256
Cefradine,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2849.7	Semi standard non polar	33892256
Cefradine,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2731.3	Standard non polar	33892256
Cefradine,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	4774.8	Standard polar	33892256
Cefradine,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2882.0	Semi standard non polar	33892256
Cefradine,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2754.0	Standard non polar	33892256
Cefradine,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	4084.0	Standard polar	33892256
Cefradine,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	3024.6	Semi standard non polar	33892256
Cefradine,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2803.5	Standard non polar	33892256
Cefradine,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	4286.0	Standard polar	33892256
Cefradine,3TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2879.4	Semi standard non polar	33892256
Cefradine,3TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	2829.0	Standard non polar	33892256
Cefradine,3TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CCC=CC3)[Si](C)(C)C)[C@H]2SC1	3888.3	Standard polar	33892256
Cefradine,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2979.4	Semi standard non polar	33892256
Cefradine,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2857.4	Standard non polar	33892256
Cefradine,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	4103.9	Standard polar	33892256
Cefradine,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2937.0	Semi standard non polar	33892256
Cefradine,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2901.1	Standard non polar	33892256
Cefradine,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	3867.0	Standard polar	33892256
Cefradine,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2964.5	Semi standard non polar	33892256
Cefradine,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2956.5	Standard non polar	33892256
Cefradine,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	3649.6	Standard polar	33892256
Cefradine,1TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1	3147.1	Semi standard non polar	33892256
Cefradine,1TBDMS,isomer #2	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[C@H]2SC1	3204.4	Semi standard non polar	33892256
Cefradine,1TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3082.4	Semi standard non polar	33892256
Cefradine,2TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[C@H]2SC1	3306.9	Semi standard non polar	33892256
Cefradine,2TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[C@H]2SC1	3075.0	Standard non polar	33892256
Cefradine,2TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[C@H]2SC1	4405.2	Standard polar	33892256
Cefradine,2TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3222.4	Semi standard non polar	33892256
Cefradine,2TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3081.9	Standard non polar	33892256
Cefradine,2TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4764.6	Standard polar	33892256
Cefradine,2TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3243.1	Semi standard non polar	33892256
Cefradine,2TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3121.7	Standard non polar	33892256
Cefradine,2TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4145.3	Standard polar	33892256
Cefradine,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3373.8	Semi standard non polar	33892256
Cefradine,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3137.0	Standard non polar	33892256
Cefradine,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4296.3	Standard polar	33892256
Cefradine,3TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3394.9	Semi standard non polar	33892256
Cefradine,3TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3345.6	Standard non polar	33892256
Cefradine,3TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CCC=CC3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4044.7	Standard polar	33892256
Cefradine,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3539.2	Semi standard non polar	33892256
Cefradine,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3346.9	Standard non polar	33892256
Cefradine,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4203.4	Standard polar	33892256
Cefradine,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3493.0	Semi standard non polar	33892256
Cefradine,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3407.1	Standard non polar	33892256
Cefradine,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3997.7	Standard polar	33892256
Cefradine,4TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3678.5	Semi standard non polar	33892256
Cefradine,4TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3613.3	Standard non polar	33892256
Cefradine,4TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CCC=CC3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3851.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cefradine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-80091aae9d8fe850aa25	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefradine GC-MS (1 TMS) - 70eV, Positive	splash10-001i-3900000000-f3afa9ff45849147f9a2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefradine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 10V, Positive-QTOF	splash10-0a4i-1912000000-94bd215ef6e306dfd051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 20V, Positive-QTOF	splash10-0a4i-2910000000-26a494e3da8e0d33e629	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 40V, Positive-QTOF	splash10-0a4i-9300000000-097e4f455974858cef42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 10V, Negative-QTOF	splash10-0006-0934000000-bf2ed0a2aca8acb21b3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 20V, Negative-QTOF	splash10-0a4u-2932000000-aa6e803bb5f9545a1eac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 40V, Negative-QTOF	splash10-054o-9700000000-b510a6e614beeea3bf42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 10V, Positive-QTOF	splash10-001i-0319000000-2535ee7cf529eb4fbf33	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 20V, Positive-QTOF	splash10-0apr-0943000000-2bc81312ff29a404d674	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 40V, Positive-QTOF	splash10-052f-6911000000-1bec8d8bfe5bc02f1d95	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 10V, Negative-QTOF	splash10-022a-0109000000-3219bd20c2d4b92d63cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 20V, Negative-QTOF	splash10-0a4j-1917000000-73766223250173d303de	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefradine 40V, Negative-QTOF	splash10-01ox-7900000000-ce05c848a6c064cbd4c3	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01333	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01333	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01333

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34933

KEGG Compound ID

C06897

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cephradine

METLIN ID

Not Available

PubChem Compound

38103

PDB ID

Not Available

ChEBI ID

3547

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neiss ES: Cephradine--a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. [PubMed:4572639 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [PubMed:18505790 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]

Enzyme Details

2. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [PubMed:9706043 ]
Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. [PubMed:8531138 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. [PubMed:9190878 ]

Enzyme Details

3. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]

Enzyme Details

4. Solute carrier family 22 member 6

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

References

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]

Showing metabocard for Cefradine (HMDB0015428)

MOL for HMDB0015428 (Cefradine)

3D MOL for HMDB0015428 (Cefradine)

3D SDF for HMDB0015428 (Cefradine)

3D-SDF for HMDB0015428 (Cefradine)

PDB for HMDB0015428 (Cefradine)

3D PDB for HMDB0015428 (Cefradine)

SMILES for HMDB0015428 (Cefradine)

INCHI for HMDB0015428 (Cefradine)

Structure for HMDB0015428 (Cefradine)

3D Structure for HMDB0015428 (Cefradine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

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