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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014590

Secondary Accession Numbers

HMDB14590

Metabolite Identification

Common Name

Loracarbef

Description

Loracarbef is only found in individuals that have used or taken this drug. It is a carbacephem antibiotic sometimes grouped together with the second-generation cephalosporin antibiotics. It is marketed under the trade name Lorabid.Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Chemically, carbacephems differ from cephalosporin-class antibiotics in the dihydrothiazine ring where a methylene group has been substituted for a sulfur atom. Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is structurally identical to cefaclor except for a sulfur atom that has been replaced by a methylene group. This change gives greater chemical stability in solution and allows storage at room temperature. Loracarbef, like all b-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014590
     RDKit          3D
Loracarbef
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.8296   -1.0127    1.7100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -0.8697    0.3845 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3588   -0.4897   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.3301   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -0.2903   -0.2687 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056    0.0816   -1.2072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7939    1.2899   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4975    2.5222   -0.8099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    0.4510   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188    0.2784   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    1.4543    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2101    1.3127    0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.7053   -0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7028   -0.9467    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289   -1.0435    0.7327 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505   -2.1331   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.8035   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -0.7027   -1.2188 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5495    0.0205    0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6999   -0.2795   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7976    0.5498   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7637    1.7498    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.0780    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    1.2228    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9006    1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537   -0.8602    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.8896    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -0.4205    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    0.2036   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8317    3.5544    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0379   -2.8356    0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -2.6557   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -1.3719    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -2.6951   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -1.0099   -2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7498   -1.2057   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7089    0.3352   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6317    2.4126    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    3.0190    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    1.5051    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  6  1  0
 24 19  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  5 28  1  0
  6 29  1  6
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  6
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv0541 04191212122D          

 24 26  0  0  1  0            999 V2000
    4.2917   -3.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -2.8667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0042   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -2.8667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8917   -2.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -4.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -0.9167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0042   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -4.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -0.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -1.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -5.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -5.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -4.1042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  5  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  3  6  1  1  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  2  0  0  0  0
 10  7  1  0  0  0  0
  5 11  1  1  0  0  0
 12  2  2  0  0  0  0
 10 13  1  1  0  0  0
 14  7  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17  8  2  0  0  0  0
 18 10  1  0  0  0  0
 19  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 18  2  0  0  0  0
 22 21  1  0  0  0  0
 23 20  2  0  0  0  0
 24 22  2  0  0  0  0
  3  2  1  0  0  0  0
 15  9  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014590

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1

> <INCHI_KEY>
JAPHQRWPEGVNBT-UTUOFQBUSA-N

> <FORMULA>
C16H16ClN3O4

> <MOLECULAR_WEIGHT>
349.769

> <EXACT_MASS>
349.082933722

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.60508513430199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
-2.399644435030454

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.45187646319562

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.12617361557546

> <JCHEM_PKA_STRONGEST_BASIC>
7.438256529944699

> <JCHEM_POLAR_SURFACE_AREA>
112.73000000000002

> <JCHEM_REFRACTIVITY>
86.63750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loracabef

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014590
     RDKit          3D
Loracarbef
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.8296   -1.0127    1.7100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -0.8697    0.3845 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3588   -0.4897   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.3301   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -0.2903   -0.2687 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056    0.0816   -1.2072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7939    1.2899   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4975    2.5222   -0.8099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    0.4510   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188    0.2784   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    1.4543    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2101    1.3127    0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.7053   -0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7028   -0.9467    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289   -1.0435    0.7327 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505   -2.1331   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.8035   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -0.7027   -1.2188 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5495    0.0205    0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6999   -0.2795   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7976    0.5498   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7637    1.7498    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.0780    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    1.2228    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9006    1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537   -0.8602    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.8896    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -0.4205    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    0.2036   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8317    3.5544    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0379   -2.8356    0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -2.6557   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -1.3719    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -2.6951   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -1.0099   -2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7498   -1.2057   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7089    0.3352   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6317    2.4126    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    3.0190    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    1.5051    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  6  1  0
 24 19  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  5 28  1  0
  6 29  1  6
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  6
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END

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  N   UNK     0       8.011  -6.891   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.471  -6.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.471  -5.351   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.341  -7.661   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.011  -5.351   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.398  -4.278   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.795  -2.808   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.341  -9.201   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.687  -6.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.698  -1.711   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.341  -4.581   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.398  -7.980   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       5.095  -0.241   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       7.288  -2.411   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.687  -5.351   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.687  -9.971   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.011  -9.971   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.205  -2.108   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      12.025  -7.661   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       2.808  -3.570   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.123  -1.011   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.653  -1.400   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.315  -3.967   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.241  -2.878   0.000  0.00  0.00           C+0
CONECT    1    2    4    5                                                  
CONECT    2    1   12    3                                                  
CONECT    3    5    6    2                                                  
CONECT    4    1    8    9                                                  
CONECT    5    3    1   11                                                  
CONECT    6    3    7                                                       
CONECT    7    6   10   14                                                  
CONECT    8    4   16   17                                                  
CONECT    9    4   19   15                                                  
CONECT   10    7   13   18                                                  
CONECT   11    5   15                                                       
CONECT   12    2                                                            
CONECT   13   10                                                            
CONECT   14    7                                                            
CONECT   15   11    9                                                       
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18   10   20   21                                                  
CONECT   19    9                                                            
CONECT   20   18   23                                                       
CONECT   21   18   22                                                       
CONECT   22   21   24                                                       
CONECT   23   20   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0014590
HETATM    1  N1  UNL     1       1.830  -1.013   1.710  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.360  -0.870   0.385  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.359  -0.490  -0.611  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.687  -0.330  -1.813  1.00  0.00           O  
HETATM    5  N2  UNL     1       0.009  -0.290  -0.269  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.006   0.082  -1.207  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.794   1.290  -0.858  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.498   2.522  -0.810  1.00  0.00           O  
HETATM    9  N3  UNL     1      -2.906   0.451  -0.636  1.00  0.00           N  
HETATM   10  C5  UNL     1      -4.219   0.278  -0.147  1.00  0.00           C  
HETATM   11  C6  UNL     1      -5.050   1.454   0.050  1.00  0.00           C  
HETATM   12  O3  UNL     1      -6.210   1.313   0.482  1.00  0.00           O  
HETATM   13  O4  UNL     1      -4.562   2.705  -0.237  1.00  0.00           O  
HETATM   14  C7  UNL     1      -4.703  -0.947   0.137  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -6.329  -1.043   0.733  1.00  0.00          CL  
HETATM   16  C8  UNL     1      -3.851  -2.133  -0.066  1.00  0.00           C  
HETATM   17  C9  UNL     1      -2.393  -1.804  -0.190  1.00  0.00           C  
HETATM   18  C10 UNL     1      -2.265  -0.703  -1.219  1.00  0.00           C  
HETATM   19  C11 UNL     1       3.549   0.020   0.347  1.00  0.00           C  
HETATM   20  C12 UNL     1       4.700  -0.279  -0.352  1.00  0.00           C  
HETATM   21  C13 UNL     1       5.798   0.550  -0.383  1.00  0.00           C  
HETATM   22  C14 UNL     1       5.764   1.750   0.317  1.00  0.00           C  
HETATM   23  C15 UNL     1       4.629   2.078   1.026  1.00  0.00           C  
HETATM   24  C16 UNL     1       3.547   1.223   1.034  1.00  0.00           C  
HETATM   25  H1  UNL     1       1.305  -1.901   1.841  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.554  -0.860   2.452  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.744  -1.890   0.087  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.272  -0.420   0.726  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.623   0.204  -2.262  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.832   3.554   0.214  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.038  -2.836   0.773  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.146  -2.656  -1.015  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.074  -1.372   0.793  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.821  -2.695  -0.439  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.651  -1.010  -2.215  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.750  -1.206  -0.904  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.709   0.335  -0.924  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.632   2.413   0.297  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.640   3.019   1.557  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.677   1.505   1.594  1.00  0.00           H  
CONECT    1    2   25   26
CONECT    2    3   19   27
CONECT    3    4    4    5
CONECT    5    6   28
CONECT    6    7   18   29
CONECT    7    8    8    9
CONECT    9   10   18
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   13   30
CONECT   14   15   16
CONECT   16   17   31   32
CONECT   17   18   33   34
CONECT   18   35
CONECT   19   20   20   24
CONECT   20   21   36
CONECT   21   22   22   37
CONECT   22   23   38
CONECT   23   24   24   39
CONECT   24   40
END

HMDB0014590
     RDKit          3D
Loracarbef
 40 42  0  0  0  0  0  0  0  0999 V2000
    1.8296   -1.0127    1.7100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -0.8697    0.3845 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3588   -0.4897   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.3301   -1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -0.2903   -0.2687 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056    0.0816   -1.2072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7939    1.2899   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4975    2.5222   -0.8099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    0.4510   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188    0.2784   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    1.4543    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2101    1.3127    0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.7053   -0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7028   -0.9467    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289   -1.0435    0.7327 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505   -2.1331   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.8035   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -0.7027   -1.2188 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5495    0.0205    0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6999   -0.2795   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7976    0.5498   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7637    1.7498    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.0780    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    1.2228    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9006    1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537   -0.8602    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.8896    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -0.4205    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    0.2036   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8317    3.5544    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0379   -2.8356    0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -2.6557   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -1.3719    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -2.6951   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -1.0099   -2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7498   -1.2057   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7089    0.3352   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6317    2.4126    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    3.0190    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    1.5051    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  6  1  0
 24 19  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  5 28  1  0
  6 29  1  6
 13 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  6
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
LORACABEF	ChEBI
Loracarbefum	ChEBI
Carbac	HMDB
Lilly brand OF loracarbef monohydrate	HMDB
Lorafem	HMDB
Lorax	HMDB
Monarch brand OF loracarbef monohydrate	HMDB
Zambon brand OF loracarbef monohydrate	HMDB
Lorabid	HMDB
Lilly brand OF loracarbef	HMDB
Syntex brand OF loracarbef monohydrate	HMDB
Loracarbef monohydrate	HMDB

Chemical Formula

C₁₆H₁₆ClN₃O₄

Average Molecular Weight

349.769

Monoisotopic Molecular Weight

349.082933722

IUPAC Name

(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

loracabef

CAS Registry Number

76470-66-1

SMILES

N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1

InChI Key

JAPHQRWPEGVNBT-UTUOFQBUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbacephems. These are a new class of beta-lactam antibiotics similar in structure to the cephalosporins. They differ from cephalosporins, however, in the substitution of a sulfur atom in the dihydrothiazine ring with a methylene group to form a tetrahydropyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Carbacephems

Alternative Parents

Substituents

Carbacephem
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Tetrahydropyridine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Vinylogous halide
Amino acid or derivatives
Azetidine
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Haloalkene
Chloroalkene
Vinyl halide
Vinyl chloride
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organochloride
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

zwitterion (CHEBI:214480 )
carbacephem (CHEBI:214480 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014590)
Membrane (HMDB: HMDB0014590)

Source

Exogenous

Exogenous (HMDB: HMDB0014590)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.32 g/L	Not Available
LogP	0.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	0.55	ALOGPS
logP	-2.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.64 m³·mol⁻¹	ChemAxon
Polarizability	32.61 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	183.107	30932474
DeepCCS	[M-H]-	180.711	30932474
DeepCCS	[M-2H]-	214.357	30932474
DeepCCS	[M+Na]+	189.189	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	181.8	32859911
AllCCS	[M+Na]+	182.6	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.16 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6612 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	132.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1509.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	308.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	374.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	505.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	813.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	319.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1088.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	321.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	160.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loracarbef	N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1	4302.3	Standard polar	33892256
Loracarbef	N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1	2814.2	Standard non polar	33892256
Loracarbef	N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1	3044.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Loracarbef,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N12	2846.0	Semi standard non polar	33892256
Loracarbef,1TMS,isomer #2	C[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1	2893.6	Semi standard non polar	33892256
Loracarbef,1TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@H](N)C1=CC=CC=C1)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	2758.0	Semi standard non polar	33892256
Loracarbef,2TMS,isomer #1	C[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	2846.3	Semi standard non polar	33892256
Loracarbef,2TMS,isomer #1	C[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	2758.2	Standard non polar	33892256
Loracarbef,2TMS,isomer #1	C[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	4043.4	Standard polar	33892256
Loracarbef,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N12	2716.7	Semi standard non polar	33892256
Loracarbef,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N12	2714.8	Standard non polar	33892256
Loracarbef,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N12	4270.2	Standard polar	33892256
Loracarbef,2TMS,isomer #3	C[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C	2842.8	Semi standard non polar	33892256
Loracarbef,2TMS,isomer #3	C[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C	2831.1	Standard non polar	33892256
Loracarbef,2TMS,isomer #3	C[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C	4128.3	Standard polar	33892256
Loracarbef,2TMS,isomer #4	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	2758.0	Semi standard non polar	33892256
Loracarbef,2TMS,isomer #4	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	2763.2	Standard non polar	33892256
Loracarbef,2TMS,isomer #4	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	3970.7	Standard polar	33892256
Loracarbef,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N12	2835.9	Semi standard non polar	33892256
Loracarbef,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N12	2910.3	Standard non polar	33892256
Loracarbef,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N12	3814.5	Standard polar	33892256
Loracarbef,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	2758.3	Semi standard non polar	33892256
Loracarbef,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	2851.4	Standard non polar	33892256
Loracarbef,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C)C1=CC=CC=C1	3704.5	Standard polar	33892256
Loracarbef,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	2811.9	Semi standard non polar	33892256
Loracarbef,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	2912.1	Standard non polar	33892256
Loracarbef,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	3775.9	Standard polar	33892256
Loracarbef,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N12	2835.4	Semi standard non polar	33892256
Loracarbef,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N12	2993.6	Standard non polar	33892256
Loracarbef,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N12	3540.0	Standard polar	33892256
Loracarbef,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N12	3060.3	Semi standard non polar	33892256
Loracarbef,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1	3059.9	Semi standard non polar	33892256
Loracarbef,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](N)C1=CC=CC=C1)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	2988.4	Semi standard non polar	33892256
Loracarbef,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	3251.6	Semi standard non polar	33892256
Loracarbef,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	3160.7	Standard non polar	33892256
Loracarbef,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)C1=CC=CC=C1	4133.4	Standard polar	33892256
Loracarbef,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N12	3170.3	Semi standard non polar	33892256
Loracarbef,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N12	3105.0	Standard non polar	33892256
Loracarbef,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N12	4305.1	Standard polar	33892256
Loracarbef,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3294.9	Semi standard non polar	33892256
Loracarbef,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3218.6	Standard non polar	33892256
Loracarbef,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	4128.0	Standard polar	33892256
Loracarbef,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3163.7	Semi standard non polar	33892256
Loracarbef,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3175.1	Standard non polar	33892256
Loracarbef,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	4052.6	Standard polar	33892256
Loracarbef,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3510.3	Semi standard non polar	33892256
Loracarbef,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3478.6	Standard non polar	33892256
Loracarbef,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3974.0	Standard polar	33892256
Loracarbef,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3365.4	Semi standard non polar	33892256
Loracarbef,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3415.5	Standard non polar	33892256
Loracarbef,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C(=O)N([C@@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(Cl)CC[C@H]12)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3939.1	Standard polar	33892256
Loracarbef,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	3458.6	Semi standard non polar	33892256
Loracarbef,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	3497.6	Standard non polar	33892256
Loracarbef,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12	3929.3	Standard polar	33892256
Loracarbef,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3662.0	Semi standard non polar	33892256
Loracarbef,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3712.0	Standard non polar	33892256
Loracarbef,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(Cl)CC[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N12	3798.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Loracarbef GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8901000000-9624c4237beed0fc58b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loracarbef GC-MS (1 TMS) - 70eV, Positive	splash10-004i-6911000000-1942c1bc1b579dcb17ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loracarbef GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loracarbef GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 10V, Positive-QTOF	splash10-0pvi-0946000000-df5d2ead7c26276f85f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 20V, Positive-QTOF	splash10-0aor-1930000000-9d4196e112fdc37ad21b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 40V, Positive-QTOF	splash10-0a4i-4900000000-57e592b2ff0c830fc344	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 10V, Negative-QTOF	splash10-0002-0319000000-e45ecb0b8853bd1bf498	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 20V, Negative-QTOF	splash10-052r-1901000000-ffe4f565f43063b475b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 40V, Negative-QTOF	splash10-0a6u-8900000000-e8d02c2084b2878efcda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 10V, Negative-QTOF	splash10-0udi-0009000000-b7a3c9f8668fbd31bcde	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 20V, Negative-QTOF	splash10-0uea-8916000000-63309ef2348514c74998	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 40V, Negative-QTOF	splash10-001i-9210000000-df0fe7334b3e12739576	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 10V, Positive-QTOF	splash10-0f89-0109000000-ab09a95a465c7b11929f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 20V, Positive-QTOF	splash10-001i-0619000000-7bcf73b1d7af848563db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loracarbef 40V, Positive-QTOF	splash10-0a4i-4921000000-9eb7cf6e6a3cb01d371d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00447	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00447	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00447

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447635

KEGG Compound ID

C08109

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loracarbef

METLIN ID

Not Available

PubChem Compound

5284585

PDB ID

Not Available

ChEBI ID

47544

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Copper RD: The carbacephems: a new beta-lactam antibiotic class. Am J Med. 1992 Jun 22;92(6A):2S-6S. [PubMed:1621741 ]
Brogden RN, McTavish D: Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May;45(5):716-36. [PubMed:7686466 ]
Dantzig AH, Duckworth DC, Tabas LB: Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta. 1994 Apr 20;1191(1):7-13. [PubMed:8155686 ]
Force RW, Nahata MC: Loracarbef: a new orally administered carbacephem antibiotic. Ann Pharmacother. 1993 Mar;27(3):321-9. [PubMed:8453172 ]

Transporters

Enzyme Details

1. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565 ]

Enzyme Details

2. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Boll M, Herget M, Wagener M, Weber WM, Markovich D, Biber J, Clauss W, Murer H, Daniel H: Expression cloning and functional characterization of the kidney cortex high-affinity proton-coupled peptide transporter. Proc Natl Acad Sci U S A. 1996 Jan 9;93(1):284-9. [PubMed:8552623 ]

Showing metabocard for Loracarbef (HMDB0014590)

MOL for HMDB0014590 (Loracarbef)

3D MOL for HMDB0014590 (Loracarbef)

3D SDF for HMDB0014590 (Loracarbef)

3D-SDF for HMDB0014590 (Loracarbef)

PDB for HMDB0014590 (Loracarbef)

3D PDB for HMDB0014590 (Loracarbef)

SMILES for HMDB0014590 (Loracarbef)

INCHI for HMDB0014590 (Loracarbef)

Structure for HMDB0014590 (Loracarbef)

3D Structure for HMDB0014590 (Loracarbef)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References

References