NP-MRD: Showing NP-Card for (6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0235571)

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Record Information

Version

2.0

Created at

2022-09-06 18:15:10 UTC

Updated at

2022-09-06 18:15:11 UTC

NP-MRD ID

NP0235571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

Cefuroxime, also known as zinacef danmark or sharox, belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group. Cefuroxime is a drug which is used for the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections. Cefuroxime is an extremely weak basic (essentially neutral) compound (based on its pKa). (6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. (6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was first documented in 1996 (PMID: 8799689). A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain (PMID: 11168076) (PMID: 11322179) (PMID: 11581233) (PMID: 12141712).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212162D          

 30 32  0  0  1  0            999 V2000
    9.8459   -4.6691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8459   -5.4940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -5.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2748   -5.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2748   -4.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -4.2566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0210   -4.6691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0210   -5.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -4.2566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -4.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -5.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -5.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8777   -4.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0001   -5.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -6.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8360   -7.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647   -7.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519   -4.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8459   -3.8433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4713   -4.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -4.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706   -5.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052   -5.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8776   -3.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7246   -5.4950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4249   -5.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1301   -5.4927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4247   -6.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941   -3.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5942   -2.1770    0.0000 C   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
 18 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
 18 23  2  0  0  0  0
 13 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.1178   -0.0439   -3.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202    0.8662   -2.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810    0.7804   -1.3982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854    0.6244   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856    0.5160    0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    0.3616    1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    0.5533    0.5049 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    0.4301    1.5314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6895    1.4255    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334    2.6197    1.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    0.5260    0.8600 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.2906    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    1.1178    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9093    1.7180    1.7082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0969    1.3758   -0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8099   -0.3999   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9687   -0.9461   -1.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310   -0.7962   -1.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613   -1.5332    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7474   -1.3985    0.6340 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -2.2444    0.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.9483   -1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.6002   -0.1954 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7039   -0.5545    1.2438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2787    0.5662    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4192    0.6565   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5184    0.5492    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9703    0.3935    1.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683    0.4114    1.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.3500   -3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699   -0.1427   -3.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128   -1.0596   -2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477    0.6729   -0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    0.3054    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9968    1.3842    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -2.0868   -1.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.6328   -2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8415   -0.7797    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5635   -1.9011    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9891   -0.1415   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481   -1.7984   -2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455   -1.1400    2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4426    0.7919   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5535    0.5790    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5819    0.2822    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 16 12  2  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  4 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 11 24  1  0
 29 25  1  0
  8 24  1  0
 24 42  1  1
 22 40  1  0
 22 41  1  0
 17 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
  8 34  1  1
  7 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 26 43  1  0
 27 44  1  0
 28 45  1  0
 15 35  1  0
M  END


  Mrv0541 04191212162D          

 30 32  0  0  1  0            999 V2000
    9.8459   -4.6691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8459   -5.4940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -5.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2748   -5.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2748   -4.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -4.2566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0210   -4.6691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0210   -5.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -4.2566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -4.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -5.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -5.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8777   -4.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0001   -5.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -6.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8360   -7.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647   -7.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519   -4.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8459   -3.8433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4713   -4.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -4.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706   -5.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052   -5.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8776   -3.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7246   -5.4950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4249   -5.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1301   -5.4927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4247   -6.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941   -3.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5942   -2.1770    0.0000 C   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
 18 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
 18 23  2  0  0  0  0
 13 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1

> <INCHI_KEY>
JFPVXVDWJQMJEE-IZRZKJBUSA-N

> <FORMULA>
C16H16N4O8S

> <MOLECULAR_WEIGHT>
424.385

> <EXACT_MASS>
424.068884198

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.749728909236225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.9029734729999994

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.97507618266688

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.149449980213596

> <JCHEM_PKA_STRONGEST_BASIC>
-1.149047285054373

> <JCHEM_POLAR_SURFACE_AREA>
173.76

> <JCHEM_REFRACTIVITY>
97.16580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sharox

> <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      18.379  -8.716   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      18.379 -10.255   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      19.713 -11.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.046 -10.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.046  -8.716   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      19.713  -7.946   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      16.839  -8.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.839 -10.255   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      15.506  -7.946   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.172  -8.716   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.172 -10.255   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.506 -11.025   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.838  -7.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.400 -11.038   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.713 -12.565   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.361 -13.346   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      21.028 -13.324   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.483  -8.728   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      18.379  -7.174   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0      10.213  -7.834   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.964  -8.766   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.465 -10.241   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.023 -10.221   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      12.838  -6.382   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      23.753 -10.257   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      25.060 -11.013   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      26.376 -10.253   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      25.059 -12.560   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.176  -5.610   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.176  -4.064   0.000  0.00  0.00           C+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   24                                                  
CONECT   14    4   25                                                       
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   20   23                                                  
CONECT   19    1                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   13   29                                                       
CONECT   25   14   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefuroxim	ChEBI
Cefuroximo	ChEBI
Cefuroximum	ChEBI
Cephuroxime	ChEBI
Sharox	ChEBI
Zinacef danmark	ChEBI
CXM	Kegg
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Ketocef	HMDB
Zinacef	HMDB

Chemical Formula

C₁₆H₁₆N₄O₈S

Average Mass

424.3850 Da

Monoisotopic Mass

424.06888 Da

IUPAC Name

(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

sharox

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O

InChI Identifier

InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1

InChI Key

JFPVXVDWJQMJEE-IZRZKJBUSA-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 cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporin 3'-carbamates

Alternative Parents

Substituents

Cephalosporin 3'-carbamate
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Meta-thiazine
Furan
Heteroaromatic compound
Carbamic acid ester
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Carbonic acid derivative
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Dialkylthioether
Hemithioaminal
Thioether
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxime O-ether (CHEBI:3515 )
furans (CHEBI:3515 )
3-(carbamoyloxymethyl)cephalosporin (CHEBI:3515 )

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	-0.24	ALOGPS
logP	-0.9	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	173.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	97.17 m³·mol⁻¹	ChemAxon
Polarizability	38.75 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0015244

DrugBank ID

DB01112

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4586393

KEGG Compound ID

C06894

BioCyc ID

CPD0-2069

BiGG ID

Not Available

Wikipedia Link

Cefuroxime

METLIN ID

Not Available

PubChem Compound

5479529

PDB ID

KOV

ChEBI ID

3515

Good Scents ID

Not Available

References

General References

Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. doi: 10.2165/00003495-199652010-00009. [PubMed:8799689 ]
Sjolin J, Goscinski G, Lundholm M, Bring J, Odenholt I: Endotoxin release from Escherichia coli after exposure to tobramycin: dose-dependency and reduction in cefuroxime-induced endotoxin release. Clin Microbiol Infect. 2000 Feb;6(2):74-81. doi: 10.1046/j.1469-0691.2000.00025.x. [PubMed:11168076 ]
Lanbeck P, Paulsen O: Short-term effects of four antibiotics on DNA synthesis in endothelial cells. Pharmacol Toxicol. 2001 Apr;88(4):204-8. doi: 10.1034/j.1600-0773.2001.d01-105.x. [PubMed:11322179 ]
Leibovici L, Berger R, Gruenewald T, Yahav J, Yehezkelli Y, Milo G, Paul M, Samra Z, Pitlik SD: Departmental consumption of antibiotic drugs and subsequent resistance: a quantitative link. J Antimicrob Chemother. 2001 Oct;48(4):535-40. doi: 10.1093/jac/48.4.535. [PubMed:11581233 ]
Saenz de San Pedro B, Mayorga C, Torres MJ, Florido JF, Quiralte J, Blanca M: Boosted IgE response after anaphylaxis reaction to cefuroxime with cross-reactivity with cefotaxime. Ann Allergy Asthma Immunol. 2002 Jul;89(1):101-3. doi: 10.1016/s1081-1206(10)61919-9. [PubMed:12141712 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0235571)

MOL for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0235571 ((6r,7r)-7-{[(2z)-2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(c-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)