NP-MRD: Showing NP-Card for (6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0241625)

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Record Information

Version

2.0

Created at

2022-09-07 01:45:19 UTC

Updated at

2022-09-07 01:45:19 UTC

NP-MRD ID

NP0241625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Cefazolin, also known as cephazolin or cefamezin, 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. Cefazolin is an extremely weak basic (essentially neutral) compound (based on its pKa). (6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. (6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was first documented in 2011 (PMID: 22011388). A first-generation cephalosporin compound having methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively (PMID: 23702270) (PMID: 24462449).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    6.6714    2.2959   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6728    1.5759   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.9879    0.3204 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714    1.2376    1.0460 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    0.0361    1.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909   -1.2029    2.4192 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3977   -2.2581    1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -1.4986    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3362   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692   -1.8613   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9686   -1.6676   -2.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -2.5655   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0870   -0.5963   -1.1346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.5359   -2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571   -1.0752   -3.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880    0.4345   -1.1777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6228   -0.0961   -0.2465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827    0.5388   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604    1.5713   -0.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8910    0.0286    0.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0482    0.8860    0.8574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1043    0.7241    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9627    1.7099    0.3089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4516    2.4469    1.2482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2899    1.9526    1.5859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2960    0.7362   -0.6784 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    0.7566    1.1087 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -0.9121    1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7418    0.0147    0.6220 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2272    2.9662   -0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3342    1.5598   -1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211    2.9414   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0228   -2.8329    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840   -3.0426    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -3.3855   -1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    1.3267   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4230   -0.9449    0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1404   -1.0268    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4833    0.0342    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2004   -0.0813   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115    1.5683   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -1.6069    1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.8037    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 27  1  0
 27 28  1  0
 28  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 29  1  0
  8  9  2  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
  9 10  1  0
 10 12  1  0
 10 11  2  0
 13 26  1  0
 25 21  1  0
 16 26  1  0
 29  5  1  0
 26 41  1  6
 28 42  1  0
 28 43  1  0
  7 33  1  0
  7 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 16 36  1  6
 17 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 12 35  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>
NP0241625

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

454.5070 Da

Monoisotopic Mass

454.03001 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.4	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

External Links

HMDB ID

HMDB0015422

DrugBank ID

DB01327

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Schweizer ML, Furuno JP, Harris AD, Johnson JK, Shardell MD, McGregor JC, Thom KA, Cosgrove SE, Sakoulas G, Perencevich EN: Comparative effectiveness of nafcillin or cefazolin versus vancomycin in methicillin-susceptible Staphylococcus aureus bacteremia. BMC Infect Dis. 2011 Oct 19;11:279. doi: 10.1186/1471-2334-11-279. [PubMed:22011388 ]
Sanz-Ruiz P, Paz E, Abenojar J, Carlos del Real J, Vaquero J, Forriol F: Effects of vancomycin, cefazolin and test conditions on the wear behavior of bone cement. J Arthroplasty. 2014 Jan;29(1):16-22. doi: 10.1016/j.arth.2013.04.008. Epub 2013 May 20. [PubMed:23702270 ]
Shoji T, Hirai Y, Osawa M, Totsuka K: Cefazolin therapy for methicillin-susceptible Staphylococcus aureus bacteremia in Japan. J Infect Chemother. 2014 Mar;20(3):175-80. doi: 10.1016/j.jiac.2013.09.008. Epub 2014 Jan 16. [PubMed:24462449 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0241625)

MOL for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0241625 ((6r,7r)-7-{[1-hydroxy-2-(1,2,3,4-tetrazol-1-yl)ethylidene]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)