NP-MRD: Showing NP-Card for (6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0260968)

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Record Information

Version

2.0

Created at

2022-09-08 03:17:28 UTC

Updated at

2022-09-08 03:17:28 UTC

NP-MRD ID

NP0260968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

Cefdinir, also known as CFDN or cefzon, 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. A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2--acetylamino- and 3-vinyl side groups. (6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. Cefdinir is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

535
  Mrv0541 02231214452D          

 27 29  0  0  1  0            999 V2000
    3.7935   -0.6744    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318   -1.0832    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9220    1.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9345    0.1585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2890   -2.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9220   -0.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0863   -2.0190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3961   -0.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7404    0.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3398   -0.2652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3398    0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0989   -1.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7389   -1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2199   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775   -0.8998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 17  1  0  0  0  0
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 15  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6 20  2  0  0  0  0
  7 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
 14  9  1  1  0  0  0
  9 20  1  0  0  0  0
 10 22  2  0  0  0  0
 11 24  1  0  0  0  0
 11 26  2  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  1  6  0  0  0
 14 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.5425   -0.6841    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625   -0.0990    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -0.3404    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    0.2368   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452    1.1880   -1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4621    1.5709   -1.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533    1.7707   -2.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -0.0360   -1.3115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889    0.4656   -2.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894    1.4891   -2.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834   -0.6628   -1.6719 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6791   -0.2577   -0.5745 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -0.5198   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514   -1.1155   -1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0672   -0.2037    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    0.3927    1.4048 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983    0.7926    1.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136   -0.5395    0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.1702   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -1.2725   -0.6265 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -0.5104    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7499   -0.2378    1.8031 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3831   -0.2248    1.0464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.3063   -1.2642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4219   -1.7276    0.5065 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065   -1.3055    1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488   -1.3575    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4876   -0.5237    2.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8731    0.5524    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    2.7024   -2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -1.1577   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.2076    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3459    1.7659    2.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4921   -1.5453   -1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721    0.6502    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0076   -0.8823    2.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682   -2.1137   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -0.8987    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611   -2.2280    1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 25  1  0
 25 26  1  0
 26  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  2  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  8 24  1  0
 23 18  1  0
 11 24  1  0
 24 37  1  6
 26 38  1  0
 26 39  1  0
  2 29  1  0
  1 27  1  0
  1 28  1  0
 11 31  1  6
 12 32  1  0
 17 33  1  0
 19 34  1  0
 22 35  1  0
 22 36  1  0
  7 30  1  0
M  END

535
  Mrv0541 02231214452D          

 27 29  0  0  1  0            999 V2000
    3.7935   -0.6744    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318   -1.0832    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9220    1.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9345    0.1585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2890   -2.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9220   -0.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0863   -2.0190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3961   -0.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7404    0.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3398   -0.2652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3398    0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0989   -1.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7389   -1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2199   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775   -0.8998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 17  1  0  0  0  0
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 15  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6 20  2  0  0  0  0
  7 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
 14  9  1  1  0  0  0
  9 20  1  0  0  0  0
 10 22  2  0  0  0  0
 11 24  1  0  0  0  0
 11 26  2  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  1  6  0  0  0
 14 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0260968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

> <INCHI_KEY>
RTXOFQZKPXMALH-GHXIOONMSA-N

> <FORMULA>
C14H13N5O5S2

> <MOLECULAR_WEIGHT>
395.414

> <EXACT_MASS>
395.035809931

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
36.120500243061215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-1.6689880985905483

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.199656742659656

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.743980558998465

> <JCHEM_PKA_STRONGEST_BASIC>
7.447509232164389

> <JCHEM_POLAR_SURFACE_AREA>
158.21

> <JCHEM_REFRACTIVITY>
94.3449

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
omnicef

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 535                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.081  -1.259   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      17.606  -2.022   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      11.054   2.149   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.748   4.131   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.415   4.131   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.944   0.296   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      11.739  -4.164   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.415   1.051   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      11.054  -1.586   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      13.228  -3.769   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      15.673  -0.450   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      18.182   0.661   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.415  -0.489   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.968  -0.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.968   1.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   1.821   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -0.489   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   1.051   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   3.361   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.543  -1.191   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   1.821   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.629  -2.282   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   1.051   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.118  -1.886   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.313  -2.858   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.210  -0.534   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       8.731  -1.680   0.000  0.00  0.00           H+0
CONECT    1   13   17                                                       
CONECT    2   25   26                                                       
CONECT    3   15                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7   10                                                            
CONECT    8   13   15   16                                                  
CONECT    9   14   20                                                       
CONECT   10    7   22                                                       
CONECT   11   24   26                                                       
CONECT   12   26                                                            
CONECT   13    1    8   14   27                                             
CONECT   14    9   13   15                                                  
CONECT   15    3    8   14                                                  
CONECT   16    8   18   19                                                  
CONECT   17    1   18                                                       
CONECT   18   16   17   21                                                  
CONECT   19    4    5   16                                                  
CONECT   20    6    9   22                                                  
CONECT   21   18   23                                                       
CONECT   22   10   20   24                                                  
CONECT   23   21                                                            
CONECT   24   11   22   25                                                  
CONECT   25    2   24                                                       
CONECT   26    2   11   12                                                  
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
(6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefdinirum	ChEBI
CFDN	ChEBI
Cefzon	Kegg
Omnicef	Kegg
(6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Cefdirnir	HMDB
Abbott brand OF cefdinir	HMDB
7-(2 (2-Aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid	HMDB

Chemical Formula

C₁₄H₁₃N₅O₅S₂

Average Mass

395.4140 Da

Monoisotopic Mass

395.03581 Da

IUPAC Name

(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

omnicef

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

InChI Identifier

InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

InChI Key

RTXOFQZKPXMALH-GHXIOONMSA-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
2,4-disubstituted 1,3-thiazole
Meta-thiazine
1,3-thiazol-2-amine
Azole
Ketoxime
Tertiary carboxylic acid amide
Thiazole
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Azetidine
Carboxamide group
Amino acid
Thioether
Azacycle
Dialkylthioether
Hemithioaminal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Amine
Organic oxide
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3485 )
ketoxime (CHEBI:3485 )

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	0.02	ALOGPS
logP	-1.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.34 m³·mol⁻¹	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014675

DrugBank ID

DB00535

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB009424

KNApSAcK ID

Not Available

Chemspider ID

5291705

KEGG Compound ID

C08110

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefdinir

METLIN ID

Not Available

PubChem Compound

6915944

PDB ID

Not Available

ChEBI ID

3485

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0260968)

MOL for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0260968 ((6r,7r)-3-ethenyl-7-{[(2z)-1-hydroxy-2-(hydroxyimino)-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)