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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (3) Show 5 proteins XML

enzymes (2)transporters (3) 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

HMDB0015422

Secondary Accession Numbers

HMDB15422

Metabolite Identification

Common Name

Cefazolin

Description

Cefazolin is only found in individuals that have used or taken this drug. It is a semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. [PubChem]In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. 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.

Structure

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


  Mrv0541 04191212172D          

 30 33  0  0  1  0            999 V2000
   15.7157  -11.8006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7157  -12.6255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -13.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1446  -12.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1446  -11.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -11.3881    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8907  -11.8006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8907  -12.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1764  -11.3881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4618  -11.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4618  -12.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1764  -13.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474  -11.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8700  -13.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -13.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7058  -14.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1346  -14.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0215  -11.8074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7157  -10.9748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5874  -12.6305    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.3017  -13.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5594  -13.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3849  -13.8252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6393  -13.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9710  -12.5552    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4642  -13.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3408  -11.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6719  -11.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9401  -12.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7748  -12.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  2  0  0  0  0
 10 13  1  0  0  0  0
  4 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
  1 19  1  6  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 18 30  1  0  0  0  0
M  END

HMDB0015422
     RDKit          3D
Cefazolin
 43 46  0  0  0  0  0  0  0  0999 V2000
    8.4150    0.8800   -2.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680    0.5141   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1626   -0.6546   -1.3082 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231   -0.7766   -0.4755 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4404    0.2620   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    0.3210    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.1205    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.2069    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276    0.0129    1.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    0.4242    2.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.6038    2.8924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    0.6731    4.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.1547    2.1120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.3645    2.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306    1.2700    3.5007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -0.5788    1.9142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1542   -0.0706    0.6713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -0.2454    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639   -0.8896    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    0.2971   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667    0.0008   -1.2655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4532    0.7252   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5794    0.0737   -1.3309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1488   -1.0168   -1.9035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8419   -1.0793   -1.8754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196   -1.3260    1.7565 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9106   -1.7973    0.0701 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669   -0.5857   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    1.4602   -1.2109 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2419    1.4239   -2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8190   -0.0521   -3.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044    1.5728   -3.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5646    0.5300   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8336   -1.1390   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1965    4.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -1.1114    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    0.4554    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147   -0.0937   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    1.3936   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4536    1.6683   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -2.1545    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    0.3472   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -1.0237   -1.2981 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
  5 29  1  0
 29  2  1  0
 28  8  1  0
 26 13  1  0
 25 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  1
 17 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 26 41  1  1
 28 42  1  0
 28 43  1  0
M  END


  Mrv0541 04191212172D          

 30 33  0  0  1  0            999 V2000
   15.7157  -11.8006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7157  -12.6255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -13.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1446  -12.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1446  -11.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -11.3881    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8907  -11.8006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8907  -12.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1764  -11.3881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4618  -11.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4618  -12.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1764  -13.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474  -11.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8700  -13.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4303  -13.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7058  -14.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1346  -14.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0215  -11.8074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7157  -10.9748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5874  -12.6305    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.3017  -13.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5594  -13.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3849  -13.8252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6393  -13.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9710  -12.5552    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4642  -13.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3408  -11.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6719  -11.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9401  -12.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7748  -12.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  2  0  0  0  0
 10 13  1  0  0  0  0
  4 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
  1 19  1  6  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 18 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015422

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

> <INCHI_KEY>
MLYYVTUWGNIJIB-BXKDBHETSA-N

> <FORMULA>
C14H14N8O4S3

> <MOLECULAR_WEIGHT>
454.507

> <EXACT_MASS>
454.030013046

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
41.43772346461959

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-1.5194100909999997

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.870217506570608

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0265585266047665

> <JCHEM_PKA_STRONGEST_BASIC>
0.2573286067906708

> <JCHEM_POLAR_SURFACE_AREA>
156.08999999999997

> <JCHEM_REFRACTIVITY>
119.8562

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cefazolin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015422
     RDKit          3D
Cefazolin
 43 46  0  0  0  0  0  0  0  0999 V2000
    8.4150    0.8800   -2.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680    0.5141   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1626   -0.6546   -1.3082 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231   -0.7766   -0.4755 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4404    0.2620   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    0.3210    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.1205    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.2069    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276    0.0129    1.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    0.4242    2.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.6038    2.8924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    0.6731    4.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.1547    2.1120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.3645    2.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306    1.2700    3.5007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -0.5788    1.9142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1542   -0.0706    0.6713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -0.2454    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639   -0.8896    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    0.2971   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667    0.0008   -1.2655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4532    0.7252   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5794    0.0737   -1.3309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1488   -1.0168   -1.9035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8419   -1.0793   -1.8754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196   -1.3260    1.7565 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9106   -1.7973    0.0701 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669   -0.5857   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    1.4602   -1.2109 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2419    1.4239   -2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8190   -0.0521   -3.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044    1.5728   -3.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5646    0.5300   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8336   -1.1390   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1965    4.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -1.1114    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    0.4554    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147   -0.0937   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    1.3936   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4536    1.6683   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -2.1545    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    0.3472   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -1.0237   -1.2981 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
  5 29  1  0
 29  2  1  0
 28  8  1  0
 26 13  1  0
 25 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  1
 17 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 26 41  1  1
 28 42  1  0
 28 43  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      29.336 -22.028   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      29.336 -23.568   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      30.670 -24.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.003 -23.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.003 -22.028   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      30.670 -21.258   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      27.796 -22.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.796 -23.568   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      26.463 -21.258   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      25.129 -22.028   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      25.129 -23.568   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.463 -24.337   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      23.795 -21.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.357 -24.350   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.670 -25.877   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      29.317 -26.658   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      31.985 -26.637   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      22.440 -22.040   0.000  0.00  0.00           N+0
HETATM   19  H   UNK     0      29.336 -20.486   0.000  0.00  0.00           H+0
HETATM   20  S   UNK     0      34.696 -23.577   0.000  0.00  0.00           S+0
HETATM   21  C   UNK     0      36.030 -24.347   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      36.511 -25.808   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      38.052 -25.807   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      38.527 -24.341   0.000  0.00  0.00           C+0
HETATM   25  S   UNK     0      37.279 -23.436   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0      40.067 -24.306   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.169 -21.146   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      19.921 -22.078   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      20.422 -23.554   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      21.980 -23.534   0.000  0.00  0.00           N+0
CONECT    1    2    6    7   19                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7    2   12                                                  
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13   10   18                                                       
CONECT   14    4   20                                                       
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   27   30                                                  
CONECT   19    1                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   21                                                       
CONECT   26   24                                                            
CONECT   27   18   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   18                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015422
HETATM    1  C1  UNL     1       8.415   0.880  -2.921  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.368   0.514  -1.909  1.00  0.00           C  
HETATM    3  N1  UNL     1       7.163  -0.655  -1.308  1.00  0.00           N  
HETATM    4  N2  UNL     1       6.223  -0.777  -0.476  1.00  0.00           N  
HETATM    5  C3  UNL     1       5.440   0.262  -0.200  1.00  0.00           C  
HETATM    6  S1  UNL     1       4.050   0.321   0.948  1.00  0.00           S  
HETATM    7  C4  UNL     1       2.596  -0.121   0.097  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.278  -0.207   0.619  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.828   0.013   1.812  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.634   0.424   2.930  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.846   0.604   2.892  1.00  0.00           O  
HETATM   12  O2  UNL     1       1.092   0.673   4.225  1.00  0.00           O  
HETATM   13  N3  UNL     1      -0.577  -0.155   2.112  1.00  0.00           N  
HETATM   14  C8  UNL     1      -1.767   0.364   2.675  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.031   1.270   3.501  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.641  -0.579   1.914  1.00  0.00           C  
HETATM   17  N4  UNL     1      -3.154  -0.071   0.671  1.00  0.00           N  
HETATM   18  C10 UNL     1      -4.493  -0.245   0.246  1.00  0.00           C  
HETATM   19  O4  UNL     1      -5.264  -0.890   1.024  1.00  0.00           O  
HETATM   20  C11 UNL     1      -4.962   0.297  -1.037  1.00  0.00           C  
HETATM   21  N5  UNL     1      -6.367   0.001  -1.265  1.00  0.00           N  
HETATM   22  C12 UNL     1      -7.453   0.725  -0.923  1.00  0.00           C  
HETATM   23  N6  UNL     1      -8.579   0.074  -1.331  1.00  0.00           N  
HETATM   24  N7  UNL     1      -8.149  -1.017  -1.903  1.00  0.00           N  
HETATM   25  N8  UNL     1      -6.842  -1.079  -1.875  1.00  0.00           N  
HETATM   26  C13 UNL     1      -1.320  -1.326   1.757  1.00  0.00           C  
HETATM   27  S2  UNL     1      -0.911  -1.797   0.070  1.00  0.00           S  
HETATM   28  C14 UNL     1       0.267  -0.586  -0.489  1.00  0.00           C  
HETATM   29  S3  UNL     1       6.122   1.460  -1.211  1.00  0.00           S  
HETATM   30  H1  UNL     1       9.242   1.424  -2.399  1.00  0.00           H  
HETATM   31  H2  UNL     1       8.819  -0.052  -3.347  1.00  0.00           H  
HETATM   32  H3  UNL     1       8.004   1.573  -3.679  1.00  0.00           H  
HETATM   33  H4  UNL     1       2.565   0.530  -0.888  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.834  -1.139  -0.437  1.00  0.00           H  
HETATM   35  H6  UNL     1       0.952  -0.196   4.762  1.00  0.00           H  
HETATM   36  H7  UNL     1      -3.395  -1.111   2.495  1.00  0.00           H  
HETATM   37  H8  UNL     1      -2.504   0.455   0.049  1.00  0.00           H  
HETATM   38  H9  UNL     1      -4.415  -0.094  -1.921  1.00  0.00           H  
HETATM   39  H10 UNL     1      -4.867   1.394  -1.045  1.00  0.00           H  
HETATM   40  H11 UNL     1      -7.454   1.668  -0.410  1.00  0.00           H  
HETATM   41  H12 UNL     1      -1.248  -2.154   2.499  1.00  0.00           H  
HETATM   42  H13 UNL     1      -0.215   0.347  -0.821  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.869  -1.024  -1.298  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3   29
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   29
CONECT    6    7
CONECT    7    8   33   34
CONECT    8    9    9   28
CONECT    9   10   13
CONECT   10   11   11   12
CONECT   12   35
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   16   17   26   36
CONECT   17   18   37
CONECT   18   19   19   20
CONECT   20   21   38   39
CONECT   21   22   25
CONECT   22   23   23   40
CONECT   23   24
CONECT   24   25   25
CONECT   26   27   41
CONECT   27   28
CONECT   28   42   43
END

HMDB0015422
     RDKit          3D
Cefazolin
 43 46  0  0  0  0  0  0  0  0999 V2000
    8.4150    0.8800   -2.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680    0.5141   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1626   -0.6546   -1.3082 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2231   -0.7766   -0.4755 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4404    0.2620   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    0.3210    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.1205    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.2069    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276    0.0129    1.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    0.4242    2.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.6038    2.8924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    0.6731    4.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.1547    2.1120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.3645    2.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306    1.2700    3.5007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -0.5788    1.9142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1542   -0.0706    0.6713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -0.2454    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639   -0.8896    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    0.2971   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667    0.0008   -1.2655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4532    0.7252   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5794    0.0737   -1.3309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1488   -1.0168   -1.9035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8419   -1.0793   -1.8754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196   -1.3260    1.7565 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9106   -1.7973    0.0701 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669   -0.5857   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    1.4602   -1.2109 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2419    1.4239   -2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8190   -0.0521   -3.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044    1.5728   -3.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5646    0.5300   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8336   -1.1390   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1965    4.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -1.1114    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    0.4554    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147   -0.0937   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    1.3936   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4536    1.6683   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -2.1545    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    0.3472   -0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -1.0237   -1.2981 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
  5 29  1  0
 29  2  1  0
 28  8  1  0
 26 13  1  0
 25 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  1
 17 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 26 41  1  1
 28 42  1  0
 28 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefamezin	ChEBI
Cefazolina	ChEBI
Cefazoline	ChEBI
Cefazolinum	ChEBI
Cephamezine	ChEBI
Cephazolidin	ChEBI
Cephazolin	ChEBI
Cephazoline	ChEBI
CEZ	ChEBI
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Cefamedin	HMDB
Cefamezine	HMDB
Sodium cephazolin	HMDB
Sodium, cefazolin	HMDB
Sodium, cephazolin	HMDB
Gramaxin	HMDB
Ancef	HMDB
Cefazolin sodium	HMDB
Cephazolin sodium	HMDB
Cephazolin, sodium	HMDB
Kefzol	HMDB
Totacef	HMDB

Chemical Formula

C₁₄H₁₄N₈O₄S₃

Average Molecular Weight

454.507

Monoisotopic Molecular Weight

454.030013046

IUPAC Name

(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefazolin

CAS Registry Number

25953-19-9

SMILES

[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O

InChI Identifier

InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

InChI Key

MLYYVTUWGNIJIB-BXKDBHETSA-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 or derivatives
Aryl thioether
Alkylarylthioether
Meta-thiazine
Azole
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrazole
Thiadiazole
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Dialkylthioether
Sulfenyl compound
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:474053 )
Cephems (C06880 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0015422)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.49 g/L	Not Available
LogP	-0.58	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-1.5	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	156.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.86 m³·mol⁻¹	ChemAxon
Polarizability	41.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	198.012	31661259
DarkChem	[M-H]-	184.203	31661259
DeepCCS	[M-2H]-	224.297	30932474
DeepCCS	[M+Na]+	199.776	30932474
AllCCS	[M+H]+	194.8	32859911
AllCCS	[M+H-H2O]+	192.9	32859911
AllCCS	[M+NH4]+	196.6	32859911
AllCCS	[M+Na]+	197.1	32859911
AllCCS	[M-H]-	185.1	32859911
AllCCS	[M+Na-2H]-	185.2	32859911
AllCCS	[M+HCOO]-	185.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.93 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9371 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1700.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	58.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	424.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	199.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	744.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	314.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1377.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	209.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	257.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cefazolin	[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O	5002.8	Standard polar	33892256
Cefazolin	[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O	3332.1	Standard non polar	33892256
Cefazolin	[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O	4103.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cefazolin,1TMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C)N3C(=O)[C@@H](NC(=O)CN4C=NN=N4)[C@H]3SC2)S1	4215.0	Semi standard non polar	33892256
Cefazolin,1TMS,isomer #2	CC1=NN=C(SCC2=C(C(=O)O)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C)[C@H]3SC2)S1	4063.6	Semi standard non polar	33892256
Cefazolin,2TMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C)[C@H]3SC2)S1	3985.4	Semi standard non polar	33892256
Cefazolin,2TMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C)[C@H]3SC2)S1	3379.7	Standard non polar	33892256
Cefazolin,2TMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C)[C@H]3SC2)S1	6439.8	Standard polar	33892256
Cefazolin,1TBDMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C(C)(C)C)N3C(=O)[C@@H](NC(=O)CN4C=NN=N4)[C@H]3SC2)S1	4422.5	Semi standard non polar	33892256
Cefazolin,1TBDMS,isomer #2	CC1=NN=C(SCC2=C(C(=O)O)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C(C)(C)C)[C@H]3SC2)S1	4280.1	Semi standard non polar	33892256
Cefazolin,2TBDMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C(C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C(C)(C)C)[C@H]3SC2)S1	4376.0	Semi standard non polar	33892256
Cefazolin,2TBDMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C(C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C(C)(C)C)[C@H]3SC2)S1	3757.5	Standard non polar	33892256
Cefazolin,2TBDMS,isomer #1	CC1=NN=C(SCC2=C(C(=O)O[Si](C)(C)C(C)(C)C)N3C(=O)[C@@H](N(C(=O)CN4C=NN=N4)[Si](C)(C)C(C)(C)C)[C@H]3SC2)S1	6319.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cefazolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ai-9331300000-a190d4fa6f7addfc7f8c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefazolin GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9310500000-949cf3462e4c45379627	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefazolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefazolin 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 - Cefazolin LC-ESI-QTOF , positive-QTOF	splash10-05fr-0109500000-d35195620e6ac4356773	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin LC-ESI-QTOF , positive-QTOF	splash10-0aba-0943000000-da64d40a841f7fe440fe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin LC-ESI-QTOF , positive-QTOF	splash10-0zfr-0910000000-f074c2d1d56b5f3da552	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin LC-ESI-QTOF , positive-QTOF	splash10-0q2i-0900000000-bbd7d226d641cfe51521	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin LC-ESI-QTOF , positive-QTOF	splash10-0l1r-0900000000-18addd569fa36108660e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0pvi-0900000000-287aa1c6700ef519dedb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0q2i-0900000000-9e7cde1888a3978aed23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 10V, Positive-QTOF	splash10-05fr-0109500000-d35195620e6ac4356773	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 20V, Positive-QTOF	splash10-0aba-0953000000-486d054de7bf3c3c59f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0q2i-0900000000-854b2bd437ac40b2e4b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 30V, Positive-QTOF	splash10-0zfr-0910000000-c1f36584835748883d05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 20V, Positive-QTOF	splash10-05fs-0943000000-663a761fef5117d13f02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 30V, Positive-QTOF	splash10-0zfr-0920000000-30e9df76adf5b0ab0e2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 10V, Positive-QTOF	splash10-05fr-0109500000-a3dc371ba38a25191014	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 50V, Positive-QTOF	splash10-0l1r-0900000000-ec13af7a17d51561e88a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 50V, Positive-QTOF	splash10-0q39-0900000000-7fdfdaaae2066b530d9e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0pvi-0900000000-32fabc5e15ec2390ad50	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0q2i-0900000000-bbd7d226d641cfe51521	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cefazolin 30V, Positive-QTOF	splash10-0zfr-0910000000-f074c2d1d56b5f3da552	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 10V, Positive-QTOF	splash10-0ap0-2749700000-4a77f2bfb0a94e40248a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 20V, Positive-QTOF	splash10-00di-9442000000-ae982fa3122bc6aa8c09	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 40V, Positive-QTOF	splash10-0a6r-9328000000-5482d1c278b4443581ce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 10V, Negative-QTOF	splash10-00xu-9311000000-fc7869714720e58c02c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 20V, Negative-QTOF	splash10-001i-4920000000-c40df0bab8447e63198d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefazolin 40V, Negative-QTOF	splash10-066r-9143000000-9ff6c941993091c7a3f9	2016-08-03	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

Cytoplasm
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 DB01327	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01327	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01327

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30723

KEGG Compound ID

C06880

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefazolin

METLIN ID

Not Available

PubChem Compound

33255

PDB ID

Not Available

ChEBI ID

474053

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. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

References

Sinan S, Kockar F, Arslan O: Novel purification strategy for human PON1 and inhibition of the activity by cephalosporin and aminoglikozide derived antibiotics. Biochimie. 2006 May;88(5):565-74. Epub 2006 Jan 19. [PubMed:16600468 ]

Enzyme Details

2. Thiopurine S-methyltransferase

General function:: Involved in thiopurine S-methyltransferase activity
Specific function:: Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:: TPMT
Uniprot ID:: P51580
Molecular weight:: 28180.09

References

Kerremans AL, Lipsky JJ, Van Loon J, Gallego MO, Weinshilboum RM: Cephalosporin-induced hypoprothrombinemia: possible role for thiol methylation of 1-methyltetrazole-5-thiol and 2-methyl-1,3,4-thiadiazole-5-thiol. J Pharmacol Exp Ther. 1985 Nov;235(2):382-8. [PubMed:2865352 ]
Wood TC, Johnson KL, Naylor S, Weinshilboum RM: Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in human tissue: possible relationship to hypoprothrombinemia. Drug Metab Dispos. 2002 Oct;30(10):1123-8. [PubMed:12228189 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]

Enzyme Details

2. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Ci L, Kusuhara H, Adachi M, Schuetz JD, Takeuchi K, Sugiyama Y: Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney. Mol Pharmacol. 2007 Jun;71(6):1591-7. Epub 2007 Mar 7. [PubMed:17344354 ]

Enzyme Details

3. 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

Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
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 ]
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 ]
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 Cefazolin (HMDB0015422)

MOL for HMDB0015422 (Cefazolin)

3D MOL for HMDB0015422 (Cefazolin)

3D SDF for HMDB0015422 (Cefazolin)

3D-SDF for HMDB0015422 (Cefazolin)

PDB for HMDB0015422 (Cefazolin)

3D PDB for HMDB0015422 (Cefazolin)

SMILES for HMDB0015422 (Cefazolin)

INCHI for HMDB0015422 (Cefazolin)

Structure for HMDB0015422 (Cefazolin)

3D Structure for HMDB0015422 (Cefazolin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

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Transporters

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