NP-MRD: Showing NP-Card for (6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0283587)

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Record Information

Version

2.0

Created at

2022-09-09 10:54:58 UTC

Updated at

2022-09-09 10:54:59 UTC

NP-MRD ID

NP0283587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Cefadroxil, also known as CDX or sumacef, belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring. Cefadroxil is a drug which is used for the treatment of the following infections (skin, uti, ent) caused by; s. Pneumoniae, h. Influenzae, staphylococci, s. Pyogenes (group a beta-hemolytic streptococci), e. Coli, p. Mirabilis, klebsiella sp, coagulase-negative staphylococci and streptococcus pyogenes. Cefadroxil is a very strong basic compound (based on its pKa). (6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. (6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was first documented in 2013 (PMID: 23224978). A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton (PMID: 23959853) (PMID: 24080658) (PMID: 24412692) (PMID: 24667741).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212172D          

 26 28  0  0  1  0            999 V2000
   17.8239   -8.7812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8239   -9.6062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384  -10.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2529   -9.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2529   -8.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384   -8.3687    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9989   -8.7812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9989   -9.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2844   -8.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5698   -8.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5698   -9.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2844  -10.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8553   -8.3687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.9784  -10.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384  -10.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8140  -11.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2429  -11.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1293   -8.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4158   -8.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7021   -8.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7021   -9.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4158  -10.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1293   -9.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8553   -7.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8239   -7.9553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9953  -10.0203    0.0000 O   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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  1  0  0  0
  1 25  1  6  0  0  0
 21 26  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.3647   -0.8670    0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1070   -0.4661    0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621    0.8150    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7913    1.8678    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8619    1.5858    1.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5129    3.1876    0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    1.1656   -0.5468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396    1.9807   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    3.0387    0.1262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075    1.0356   -1.4391 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0390    0.0261   -0.8915 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633   -0.1466   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434    0.5934   -2.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.1829   -0.8739 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4974   -1.9676    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327   -0.6625   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -1.5170    0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -1.0899    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7100    0.2236    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8396    0.6308    1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    1.0703    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    0.6311   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1809    0.5350   -1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4719   -1.2256   -1.6602 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526   -1.5378   -0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856   -0.5699    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4108   -0.4335    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3859   -1.9823    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142    3.3907   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    1.6138   -2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -0.5824   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -1.8662   -1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695   -2.9314    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -1.4888    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8527   -2.5502    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8891   -1.7560    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8209    0.9940    2.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919    2.0978    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2993    1.3324   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157    1.0170   -2.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -1.4725    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6468   -2.5365    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  2  1  1  0
  2  3  2  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  7 23  1  0
 22 16  1  0
 10 23  1  0
 23 40  1  6
 25 41  1  0
 25 42  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 10 30  1  6
 11 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
  6 29  1  0
M  END


  Mrv0541 04191212172D          

 26 28  0  0  1  0            999 V2000
   17.8239   -8.7812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8239   -9.6062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384  -10.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2529   -9.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2529   -8.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384   -8.3687    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9989   -8.7812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9989   -9.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2844   -8.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5698   -8.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5698   -9.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2844  -10.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8553   -8.3687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.9784  -10.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384  -10.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8140  -11.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2429  -11.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1293   -8.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4158   -8.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7021   -8.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7021   -9.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4158  -10.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1293   -9.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8553   -7.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8239   -7.9553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9953  -10.0203    0.0000 O   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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  1  0  0  0
  1 25  1  6  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283587

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1

> <INCHI_KEY>
BOEGTKLJZSQCCD-UEKVPHQBSA-N

> <FORMULA>
C16H17N3O5S

> <MOLECULAR_WEIGHT>
363.388

> <EXACT_MASS>
363.088891359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.86177537632552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-2.4485235229519144

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.47951977832049

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.445403259534226

> <JCHEM_PKA_STRONGEST_BASIC>
7.429743431066661

> <JCHEM_POLAR_SURFACE_AREA>
132.96

> <JCHEM_REFRACTIVITY>
90.95450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cephadroxil

> <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      33.271 -16.392   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      33.271 -17.932   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      34.605 -18.702   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.939 -17.932   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.939 -16.392   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      34.605 -15.622   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      31.731 -16.392   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.731 -17.932   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      30.398 -15.622   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      29.064 -16.392   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.064 -17.932   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      30.398 -18.702   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      27.730 -15.622   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.293 -18.714   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.605 -20.241   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      33.253 -21.022   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      35.920 -21.001   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      26.375 -16.404   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.043 -15.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.711 -16.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.711 -17.943   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.043 -18.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.375 -17.943   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      27.730 -14.077   0.000  0.00  0.00           N+0
HETATM   25  H   UNK     0      33.271 -14.850   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0      22.391 -18.705   0.000  0.00  0.00           O+0
CONECT    1    2    6    7   25                                             
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                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   13                                                            
CONECT   25    1                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
CDX	ChEBI
Cefadroxil anhydrous	ChEBI
Cefadroxilo	ChEBI
Cefadroxilum	ChEBI
Cephadroxil	ChEBI
D-Cefadroxil	ChEBI
Sumacef	Kegg
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Cefadroxil monohydrate	HMDB
Cefradroxil	HMDB
4-Hydroxycephalexin	HMDB
Anhydrous, cefadroxil	HMDB
BL S 578	HMDB
BL S578	HMDB
BL-S578	HMDB
Bidocef	HMDB
4 Hydroxycephalexin	HMDB
BL-S 578	HMDB
BLS 578	HMDB
Cephadroxyl	HMDB
Duricef	HMDB
Monohydrate, cefadroxil	HMDB
Ultracef	HMDB

Chemical Formula

C₁₆H₁₇N₃O₅S

Average Mass

363.3880 Da

Monoisotopic Mass

363.08889 Da

IUPAC Name

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

Traditional Name

cephadroxil

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1

InChI Key

BOEGTKLJZSQCCD-UEKVPHQBSA-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 dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4710 )
dibenzooxepine (CHEBI:4710 )

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	0.51	ALOGPS
logP	-2.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	7.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	35.86 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

HMDB0015271

DrugBank ID

DB01140

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

43630

KEGG Compound ID

C06878

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefadroxil

METLIN ID

Not Available

PubChem Compound

47965

PDB ID

Not Available

ChEBI ID

3479

Good Scents ID

Not Available

References

General References

Posada MM, Smith DE: Relevance of PepT1 in the intestinal permeability and oral absorption of cefadroxil. Pharm Res. 2013 Apr;30(4):1017-25. doi: 10.1007/s11095-012-0937-8. Epub 2012 Dec 7. [PubMed:23224978 ]
Posada MM, Smith DE: In vivo absorption and disposition of cefadroxil after escalating oral doses in wild-type and PepT1 knockout mice. Pharm Res. 2013 Nov;30(11):2931-9. doi: 10.1007/s11095-013-1168-3. [PubMed:23959853 ]
Huh Y, Keep RF, Smith DE: Impact of lipopolysaccharide-induced inflammation on the disposition of the aminocephalosporin cefadroxil. Antimicrob Agents Chemother. 2013 Dec;57(12):6171-8. doi: 10.1128/AAC.01497-13. Epub 2013 Sep 30. [PubMed:24080658 ]
Jin HE, Kim IB, Kim YC, Cho KH, Maeng HJ: Determination of cefadroxil in rat plasma and urine using LC-MS/MS and its application to pharmacokinetic and urinary excretion studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 1;947-948:103-10. doi: 10.1016/j.jchromb.2013.12.027. Epub 2013 Dec 30. [PubMed:24412692 ]
Ware MA, Bennett GJ: Case report: Long-standing complex regional pain syndrome relieved by a cephalosporin antibiotic. Pain. 2014 Jul;155(7):1412-1415. doi: 10.1016/j.pain.2014.03.014. Epub 2014 Mar 22. [PubMed:24667741 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0283587)

MOL for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0283587 ((6r,7r)-7-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)