NP-MRD: Showing NP-Card for (6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0163105)

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Record Information

Version

2.0

Created at

2022-09-02 21:38:52 UTC

Updated at

2022-09-02 21:38:52 UTC

NP-MRD ID

NP0163105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Cephapirin, also known as cefapirin or CEPR, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Cephapirin is a drug which is used for treatment of infections caused by susceptible bacteria. Cephapirin is a strong basic compound (based on its pKa). (6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. (6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was first documented in 1990 (PMID: 2114604). A cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton (PMID: 19246140) (PMID: 23948762) (PMID: 24224523).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305041817312D          

 29 31  0  0  0  0            999 V2000
10001.4804 9998.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7666 9997.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1963 9997.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.938710000.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9387 9999.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3551 9999.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.224110000.8252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.509410000.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.794810000.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.080210000.4126    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5094 9999.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.9081 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6219 9999.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.3378 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0536 9999.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3378 9998.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.764610001.2377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.364710001.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.650310002.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.935710001.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.935710000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.650210000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.364710000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479710000.8252    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10000.765210000.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7652 9999.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4797 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1942 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.194210000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  7  1  1  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 18 19  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 28 12  1  0  0  0  0
 25 17  1  6  0  0  0
  1 27  1  0  0  0  0
 10 23  1  0  0  0  0
 25  4  1  0  0  0  0
  4  5  1  0  0  0  0
 26  5  1  0  0  0  0
M  END

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -7.3522    1.5318   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6608    0.4907    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3358   -0.3137    0.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2907    0.3844    0.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6227   -0.6014    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563   -0.4781    0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4236   -1.4583    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9107   -2.7368   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -3.6356   -0.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209   -3.0971   -0.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755   -1.3084    0.1710 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -1.5448   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293   -2.1577   -1.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -0.7695    0.3078 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4493    0.5062   -0.1355 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.9362    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.2103    0.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813    2.2366   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082    1.8906   -1.5730 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817    0.9633   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7332   -0.4053   -0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8079   -1.0704   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8775   -0.4172    0.2241 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9549    0.9227    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8866    1.6023   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253   -0.6858    1.2345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8939    0.9706    1.4366 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6559    0.8630    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8671    1.0331   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0804    2.0266   -0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6272    2.2368   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9297   -0.4273    1.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982   -1.5582    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -3.9119    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.3515    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    1.1487   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308    2.7608    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    2.8542   -0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774   -0.9619   -1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7837   -2.1459   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8167    1.4195    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9078    2.6816   -0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.2706    2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1327    1.0534    2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0498    1.5841    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 27  1  0
 27 28  1  0
 28  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  7  2  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 11 26  1  0
 25 20  1  0
 14 26  1  0
 26 43  1  1
 28 44  1  0
 28 45  1  0
  5 32  1  0
  5 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 14 35  1  1
 15 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 22 40  1  0
 24 41  1  0
 25 42  1  0
 10 34  1  0
M  END


  Mrv1652305041817312D          

 29 31  0  0  0  0            999 V2000
10001.4804 9998.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7666 9997.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1963 9997.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.938710000.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9387 9999.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3551 9999.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.224110000.8252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.509410000.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.794810000.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.080210000.4126    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5094 9999.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.9081 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6219 9999.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.3378 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0536 9999.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3378 9998.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.764610001.2377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.364710001.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.650310002.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.935710001.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.935710000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.650210000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.364710000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479710000.8252    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10000.765210000.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7652 9999.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4797 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1942 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.194210000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  7  1  1  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 18 19  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 28 12  1  0  0  0  0
 25 17  1  6  0  0  0
  1 27  1  0  0  0  0
 10 23  1  0  0  0  0
 25  4  1  0  0  0  0
  4  5  1  0  0  0  0
 26  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

> <INCHI_KEY>
UQLLWWBDSUHNEB-CZUORRHYSA-N

> <FORMULA>
C17H17N3O6S2

> <MOLECULAR_WEIGHT>
423.463

> <EXACT_MASS>
423.055876671

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
40.62512857543864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-2.001103457744709

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.539261443316581

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5406870467118727

> <JCHEM_PKA_STRONGEST_BASIC>
4.999447525217403

> <JCHEM_POLAR_SURFACE_AREA>
125.9

> <JCHEM_REFRACTIVITY>
102.4307

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
CEPR

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-18         0                                  
HETATM    1  C   UNK     0    8669.4308663.588   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.0988662.816   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.7668662.816   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8666.5528667.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.5528665.896   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8665.4638664.807   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8665.2188668.207   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8663.8848667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.5508668.207   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0    8661.2168667.437   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0    8663.8848665.896   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8672.0958665.128   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8673.4288665.896   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8674.7648665.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8676.1008665.896   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8674.7648663.588   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0    8668.0948668.977   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8659.8818669.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.5478670.517   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8657.2138669.747   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8657.2138668.207   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8658.5478667.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8659.8818668.207   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0    8669.4298668.207   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0    8668.0958667.437   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0    8668.0958665.897   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0    8669.4298665.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.7638665.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.7638667.437   0.000  0.00  0.00           C+0
CONECT    1    2    3   27                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7   25    5                                                  
CONECT    5    6    4   26                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9   23                                                       
CONECT   11    8                                                            
CONECT   12   13   28                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   25                                                            
CONECT   18   19   23                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   22   20                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   10                                                  
CONECT   24   25   29                                                       
CONECT   25   24   26   17    4                                             
CONECT   26   25   27    5                                                  
CONECT   27   28   26    1                                                  
CONECT   28   27   29   12                                                  
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefapirin	ChEBI
Cefapirina	ChEBI
Cefapirine	ChEBI
Cefapirinum	ChEBI
Cefaprin	ChEBI
Cephapirine	ChEBI
CEPR	ChEBI
Metricure	Kegg
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Cefadyl	HMDB
Monosodium salt, cephapirin	HMDB
Salt, cephapirin monosodium	HMDB
BL p 1322	HMDB
Bristol-myers brand OF cephapirin sodium	HMDB
Cephapirin, sodium	HMDB
Apothecon brand OF cephapirin sodium	HMDB
Cephapirin sodium	HMDB
Céfaloject	HMDB
Sodium cephapirin	HMDB
BL-p 1322	HMDB
Brisfirina	HMDB
Bristol-myers squibb brand OF cephapirin sodium	HMDB
Cephapirin monosodium salt	HMDB
Cephapirin	KEGG

Chemical Formula

C₁₇H₁₇N₃O₆S₂

Average Mass

423.4630 Da

Monoisotopic Mass

423.05588 Da

IUPAC Name

(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

CEPR

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O

InChI Identifier

InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

InChI Key

UQLLWWBDSUHNEB-CZUORRHYSA-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 n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Cephem
Aryl thioether
Alkylarylthioether
Meta-thiazine
Dicarboxylic acid or derivatives
Pyridine
Heteroaromatic compound
Beta-lactam
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Azetidine
Azacycle
Organoheterocyclic compound
Carboximidic acid
Carboximidic acid derivative
Dialkylthioether
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Hemithioaminal
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:554446 )

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	0.18	ALOGPS
logP	-2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	125.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	102.43 m³·mol⁻¹	ChemAxon
Polarizability	40.63 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

HMDB0015270

DrugBank ID

DB01139

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002317

KNApSAcK ID

Not Available

Chemspider ID

28486

KEGG Compound ID

C06896

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cephapirin

METLIN ID

Not Available

PubChem Compound

30699

PDB ID

Not Available

ChEBI ID

554446

Good Scents ID

Not Available

References

General References

Simonet M, Herrmann JL, Gehanno P, Veron M: [Activity of cefapirin against bacterial strains isolated from acute otitis media in children]. Pathol Biol (Paris). 1990 May;38(5):352-4. [PubMed:2114604 ]
Peterson JW, O'Meara TA, Seymour MD, Wang W, Gu B: Sorption mechanisms of cephapirin, a veterinary antibiotic, onto quartz and feldspar minerals as detected by Raman spectroscopy. Environ Pollut. 2009 Jun;157(6):1849-56. doi: 10.1016/j.envpol.2009.01.017. Epub 2009 Feb 26. [PubMed:19246140 ]
Hermo MP, Gomez-Rodriguez P, Barbosa J, Barron D: Metabolomic assays of amoxicillin, cephapirin and ceftiofur in chicken muscle: application to treated chicken samples by liquid chromatography quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal. 2013 Nov;85:169-78. doi: 10.1016/j.jpba.2013.07.023. Epub 2013 Jul 30. [PubMed:23948762 ]
Cagnardi P, Locatelli C, Ferraresi C, Bronzo V, Carli S, Villa R, Zonca A: Pharmacokinetics in foremilk and antimicrobial activity of cephapirin following intramammary administration in healthy and Staphylococcus aureus-infected cows. N Z Vet J. 2014 May;62(3):146-51. doi: 10.1080/00480169.2013.865295. Epub 2014 Jan 9. [PubMed:24224523 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0163105)

MOL for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0163105 ((6r,7r)-3-[(acetyloxy)methyl]-7-{[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)