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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (4) Show 6 proteins XML

enzymes (2)transporters (4) Show 6 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014707

Secondary Accession Numbers

HMDB14707

Metabolite Identification

Common Name

Cephalexin

Description

Cephalexin is only found in individuals that have used or taken this drug. It is a semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of cephaloridine or cephalothin, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms. [PubChem]Cephalexin, 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 cephalexin interferes with an autolysin inhibitor.

Structure

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

HMDB0014707
     RDKit          3D
Cephalexin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -5.2025    0.4699    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.0649    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.3819   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6508    1.1445   -1.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829    1.4852   -2.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    1.5459   -0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4746   -0.0171   -1.2883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391    0.3471   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530    1.3118   -2.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.8548   -1.6444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3032   -0.6925   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -1.2055   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396   -1.8581   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -0.9980    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179   -0.2836    1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -0.3050    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -0.0173   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051    0.6525   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2039    1.0454    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735    0.7639    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4724    0.1050    1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -1.3734   -1.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0854   -1.9559    0.4620 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.6941    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209    1.5887    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086    0.0523    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185    0.0085    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    2.2934   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -1.4160   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.1606    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -1.9968    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.7290    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -0.7269    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7515   -0.3157   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    0.8732   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559    1.5678    0.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193    1.0711    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.0825    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -2.0750   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    0.0740    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -1.1169    2.3157 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  2  0
 19 20  1  0
 20 21  2  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  1
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  6
 24 40  1  0
 24 41  1  0
M  END

567
  Mrv0541 02231214462D          

 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
    2.3644    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
    2.3644   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    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
    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
    6.5869   -1.3942    0.0000 C   0  0  1  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
    8.3967   -0.1739    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
    8.9789   -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 17  1  0  0  0  0
  5 17  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
 18  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 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014707

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3O4S/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/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

> <INCHI_KEY>
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

> <FORMULA>
C16H17N3O4S

> <MOLECULAR_WEIGHT>
347.389

> <EXACT_MASS>
347.093976737

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.517372137229785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
-2.145040938549694

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.912251938144717

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4520106778278037

> <JCHEM_PKA_STRONGEST_BASIC>
7.438374274238598

> <JCHEM_POLAR_SURFACE_AREA>
112.72999999999999

> <JCHEM_REFRACTIVITY>
88.97360000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cephalexin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014707
     RDKit          3D
Cephalexin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -5.2025    0.4699    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.0649    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.3819   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6508    1.1445   -1.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829    1.4852   -2.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    1.5459   -0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4746   -0.0171   -1.2883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391    0.3471   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530    1.3118   -2.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.8548   -1.6444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3032   -0.6925   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -1.2055   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396   -1.8581   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -0.9980    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179   -0.2836    1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -0.3050    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -0.0173   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051    0.6525   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2039    1.0454    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735    0.7639    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4724    0.1050    1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -1.3734   -1.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0854   -1.9559    0.4620 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.6941    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209    1.5887    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086    0.0523    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185    0.0085    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    2.2934   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -1.4160   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.1606    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -1.9968    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.7290    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -0.7269    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7515   -0.3157   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    0.8732   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559    1.5678    0.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193    1.0711    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.0825    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -2.0750   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    0.0740    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -1.1169    2.3157 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  2  0
 19 20  1  0
 20 21  2  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  1
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  6
 24 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 567                                               
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       3.080   1.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   3.041   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.296  -2.603   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      15.674  -0.325   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.359  -2.903   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   17                                                            
CONECT    5   17                                                            
CONECT    6    9   11   12                                                  
CONECT    7   10   15                                                       
CONECT    8   18                                                            
CONECT    9    1    6   10   25                                             
CONECT   10    7    9   11                                                  
CONECT   11    2    6   10                                                  
CONECT   12    6   14   17                                                  
CONECT   13    1   14                                                       
CONECT   14   12   13   16                                                  
CONECT   15    3    7   18                                                  
CONECT   16   14                                                            
CONECT   17    4    5   12                                                  
CONECT   18    8   15   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014707
HETATM    1  C1  UNL     1      -5.203   0.470   1.247  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.947   0.065   0.614  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.685   0.382  -0.667  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.651   1.144  -1.458  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.483   1.485  -2.656  1.00  0.00           O  
HETATM    6  O2  UNL     1      -5.855   1.546  -0.895  1.00  0.00           O  
HETATM    7  N1  UNL     1      -2.475  -0.017  -1.288  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.339   0.347  -2.064  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.053   1.312  -2.816  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.613  -0.855  -1.644  1.00  0.00           C  
HETATM   11  N2  UNL     1       0.303  -0.692  -0.538  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.615  -1.206  -0.522  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.040  -1.858  -1.540  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.480  -0.998   0.637  1.00  0.00           C  
HETATM   15  N3  UNL     1       1.718  -0.284   1.660  1.00  0.00           N  
HETATM   16  C9  UNL     1       3.742  -0.305   0.381  1.00  0.00           C  
HETATM   17  C10 UNL     1       4.284  -0.017  -0.849  1.00  0.00           C  
HETATM   18  C11 UNL     1       5.505   0.653  -0.962  1.00  0.00           C  
HETATM   19  C12 UNL     1       6.204   1.045   0.142  1.00  0.00           C  
HETATM   20  C13 UNL     1       5.673   0.764   1.377  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.472   0.105   1.489  1.00  0.00           C  
HETATM   22  C15 UNL     1      -1.977  -1.373  -1.238  1.00  0.00           C  
HETATM   23  S1  UNL     1      -2.085  -1.956   0.462  1.00  0.00           S  
HETATM   24  C16 UNL     1      -2.946  -0.694   1.425  1.00  0.00           C  
HETATM   25  H1  UNL     1      -5.321   1.589   1.344  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.209   0.052   2.299  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.118   0.009   0.795  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.414   2.293  -1.231  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.222  -1.416  -2.498  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.051  -0.161   0.285  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.744  -1.997   1.097  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.974   0.729   1.657  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.809  -0.727   2.589  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.752  -0.316  -1.724  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.921   0.873  -1.933  1.00  0.00           H  
HETATM   36  H12 UNL     1       7.156   1.568   0.078  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.219   1.071   2.278  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.116  -0.083   2.506  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.421  -2.075  -1.979  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.223   0.074   1.823  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.437  -1.117   2.316  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   19   35
CONECT   19   20   36
CONECT   20   21   21   37
CONECT   21   38
CONECT   22   23   39
CONECT   23   24
CONECT   24   40   41
END

HMDB0014707
     RDKit          3D
Cephalexin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -5.2025    0.4699    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    0.0649    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.3819   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6508    1.1445   -1.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829    1.4852   -2.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    1.5459   -0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4746   -0.0171   -1.2883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391    0.3471   -2.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530    1.3118   -2.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.8548   -1.6444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3032   -0.6925   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -1.2055   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396   -1.8581   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -0.9980    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7179   -0.2836    1.6602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425   -0.3050    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -0.0173   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051    0.6525   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2039    1.0454    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735    0.7639    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4724    0.1050    1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -1.3734   -1.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0854   -1.9559    0.4620 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.6941    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209    1.5887    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2086    0.0523    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185    0.0085    0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    2.2934   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -1.4160   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.1606    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -1.9968    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.7290    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -0.7269    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7515   -0.3157   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    0.8732   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559    1.5678    0.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193    1.0711    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.0825    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -2.0750   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    0.0740    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -1.1169    2.3157 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  2  0
 19 20  1  0
 20 21  2  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  1
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  6
 24 40  1  0
 24 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acid	ChEBI
7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid	ChEBI
Cefalexin	ChEBI
Cefalexina	ChEBI
Cefalexine	ChEBI
Cefalexinum	ChEBI
Celexin	ChEBI
Cepastar	ChEBI
Cepexin	ChEBI
Cephacillin	ChEBI
Ceporexin	ChEBI
CEX	ChEBI
Keflex	Kegg
(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
7-(D-a-Aminophenylacetamido)desacetoxycephalosporanate	Generator
7-(D-a-Aminophenylacetamido)desacetoxycephalosporanic acid	Generator
7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanate	Generator
7-(D-Α-aminophenylacetamido)desacetoxycephalosporanate	Generator
7-(D-Α-aminophenylacetamido)desacetoxycephalosporanic acid	Generator
7-b-(D-a-Amino-a-phenylacetylamino)-3-methyl-3-cephem-4-carboxylate	Generator
7-b-(D-a-Amino-a-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid	Generator
7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylate	Generator
7-Β-(D-α-amino-α-phenylacetylamino)-3-methyl-3-cephem-4-carboxylate	Generator
7-Β-(D-α-amino-α-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid	Generator
Cefalessina	HMDB
Cephalexin 1-hydrate	HMDB
Cephalexin hydrate	HMDB
Cephalexin monohydrate	HMDB
Cephalexine	HMDB
Cephalexinum	HMDB
Cephalexin dihydride	HMDB
Cephalexin hydrochloride	HMDB
Cephalexin, (6R-(6alpha,7beta))-isomer	HMDB
Cephalexin, monosodium salt, (6R-(6alpha,7beta))-isomer	HMDB
Cephalexin monohydrochloride	HMDB
Cephalexin monohydrochloride, monohydrate	HMDB
Cephalexin, (6R-(6alpha,7beta(s*)))-isomer	HMDB
Cephalexin, monosodium salt	HMDB
Palitrex	HMDB
Cephalexin hemihydrate	HMDB
Hydrochloride, cephalexin	HMDB
Monohydrochloride, cephalexin	HMDB
Monosodium salt cephalexin	HMDB
Cephalexin, (6R-(6alpha,7alpha(r*)))-isomer	HMDB
Ceporexine	HMDB
Dihydride, cephalexin	HMDB
Hemihydrate, cephalexin	HMDB
Monohydrate cephalexin monohydrochloride	HMDB
Monohydrate, cephalexin	HMDB
Monohydrochloride, monohydrate cephalexin	HMDB

Chemical Formula

C₁₆H₁₇N₃O₄S

Average Molecular Weight

347.389

Monoisotopic Molecular Weight

347.093976737

IUPAC Name

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

Traditional Name

cephalexin

CAS Registry Number

15686-71-2

SMILES

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

InChI Identifier

InChI=1S/C16H17N3O4S/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/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

InChI Key

ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Aralkylamine
Meta-thiazine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Azetidine
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Thioether
Hemithioaminal
Dialkylthioether
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3534 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014707)
Membrane (HMDB: HMDB0014707)

Source

Exogenous

Exogenous (HMDB: HMDB0014707)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	326.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 g/L	Not Available
LogP	0	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	178.533	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000938

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	0.55	ALOGPS
logP	-2.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	7.44	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	88.97 m³·mol⁻¹	ChemAxon
Polarizability	32.52 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]+	177.27	31661259
DarkChem	[M-H]-	170.608	31661259
DeepCCS	[M-2H]-	211.681	30932474
DeepCCS	[M+Na]+	186.818	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	175.9	32859911
AllCCS	[M+NH4]+	181.3	32859911
AllCCS	[M+Na]+	182.1	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cephalexin	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O	4358.8	Standard polar	33892256
Cephalexin	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O	2618.7	Standard non polar	33892256
Cephalexin	[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O	3105.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cephalexin,1TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CC=CC=C3)[C@H]2SC1	2945.7	Semi standard non polar	33892256
Cephalexin,1TMS,isomer #2	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1	2989.3	Semi standard non polar	33892256
Cephalexin,1TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2863.6	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	2944.8	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	2727.2	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	4300.9	Standard polar	33892256
Cephalexin,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2843.4	Semi standard non polar	33892256
Cephalexin,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2711.3	Standard non polar	33892256
Cephalexin,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	4419.5	Standard polar	33892256
Cephalexin,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2854.4	Semi standard non polar	33892256
Cephalexin,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2775.1	Standard non polar	33892256
Cephalexin,2TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	4048.4	Standard polar	33892256
Cephalexin,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2949.5	Semi standard non polar	33892256
Cephalexin,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2815.8	Standard non polar	33892256
Cephalexin,2TMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	4272.2	Standard polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2880.0	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	2850.6	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3829.8	Standard polar	33892256
Cephalexin,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2947.9	Semi standard non polar	33892256
Cephalexin,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2880.2	Standard non polar	33892256
Cephalexin,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	4060.5	Standard polar	33892256
Cephalexin,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2926.2	Semi standard non polar	33892256
Cephalexin,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2917.1	Standard non polar	33892256
Cephalexin,3TMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	3851.7	Standard polar	33892256
Cephalexin,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2964.6	Semi standard non polar	33892256
Cephalexin,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	2995.6	Standard non polar	33892256
Cephalexin,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1	3654.6	Standard polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	3173.5	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	3158.3	Semi standard non polar	33892256
Cephalexin,1TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3070.7	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	3308.5	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	3113.4	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[C@H]2SC1	4361.2	Standard polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3241.7	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3086.1	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4449.1	Standard polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3192.2	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3167.8	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4136.4	Standard polar	33892256
Cephalexin,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3359.9	Semi standard non polar	33892256
Cephalexin,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3194.9	Standard non polar	33892256
Cephalexin,2TBDMS,isomer #4	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4274.6	Standard polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3371.5	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3406.1	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4056.3	Standard polar	33892256
Cephalexin,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3532.0	Semi standard non polar	33892256
Cephalexin,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	3432.4	Standard non polar	33892256
Cephalexin,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4199.9	Standard polar	33892256
Cephalexin,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)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	3505.9	Semi standard non polar	33892256
Cephalexin,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)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	3485.4	Standard non polar	33892256
Cephalexin,3TBDMS,isomer #3	CC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)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	4022.6	Standard polar	33892256
Cephalexin,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=CC=CC=C3)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	3687.1	Semi standard non polar	33892256
Cephalexin,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=CC=CC=C3)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	3725.0	Standard non polar	33892256
Cephalexin,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=CC=CC=C3)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	3919.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cephalexin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-268bac07b4777b149217	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephalexin GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-1900000000-05009b17787cf8ff6e6d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cephalexin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cephalexin LC-ESI-QTOF , positive-QTOF	splash10-0ab9-0900000000-e1976a2fc84f1a3ef783	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cephalexin -1V, Positive-QTOF	splash10-0ab9-0900000000-e1976a2fc84f1a3ef783	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 10V, Positive-QTOF	splash10-0a4i-1912000000-5d8b84d77328a68693b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 20V, Positive-QTOF	splash10-0a4i-2910000000-9f1b122dccd5dbbc51f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 40V, Positive-QTOF	splash10-0a4i-9800000000-79dee94f80734fda674f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 10V, Negative-QTOF	splash10-000i-0934000000-513ac73d3fbd8c59475e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 20V, Negative-QTOF	splash10-0a5i-2932000000-79d8b675da05679abbc8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 40V, Negative-QTOF	splash10-054o-9710000000-f0722ea9e4937ee90457	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 10V, Negative-QTOF	splash10-029b-0219000000-67830da27d4c19dfd237	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 20V, Negative-QTOF	splash10-06r2-1906000000-55bb4625f6f1b5366ffd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 40V, Negative-QTOF	splash10-06r6-7900000000-27f1bedbf89f25b74fd5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 10V, Positive-QTOF	splash10-053s-0709000000-3233ce25df02604fa76f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 20V, Positive-QTOF	splash10-05ai-0913000000-8acc36e554702c755d5d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cephalexin 40V, Positive-QTOF	splash10-0a4i-2900000000-b1056c3fc46f54f6b3cc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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 DB00567	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00567	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00567

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25541

KEGG Compound ID

C06895

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefalexin

METLIN ID

Not Available

PubChem Compound

27447

PDB ID

Not Available

ChEBI ID

3534

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

Not Available

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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

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

Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. [PubMed:7896779 ]
Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565 ]
Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
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 ]
Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
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 ]
Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. [PubMed:9379359 ]

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

Liu W, Liang R, Ramamoorthy S, Fei YJ, Ganapathy ME, Hediger MA, Ganapathy V, Leibach FH: Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney. Biochim Biophys Acta. 1995 May 4;1235(2):461-6. [PubMed:7756356 ]
Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
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 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

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

Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172 ]
Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [PubMed:15618660 ]

Showing metabocard for Cephalexin (HMDB0014707)

MOL for HMDB0014707 (Cephalexin)

3D MOL for HMDB0014707 (Cephalexin)

3D SDF for HMDB0014707 (Cephalexin)

3D-SDF for HMDB0014707 (Cephalexin)

PDB for HMDB0014707 (Cephalexin)

3D PDB for HMDB0014707 (Cephalexin)

SMILES for HMDB0014707 (Cephalexin)

INCHI for HMDB0014707 (Cephalexin)

Structure for HMDB0014707 (Cephalexin)

3D Structure for HMDB0014707 (Cephalexin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Transporters

References

References

References

References