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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015421

Secondary Accession Numbers

HMDB15421

Metabolite Identification

Common Name

Cefamandole

Description

Cefamandole is only found in individuals that have used or taken this drug. It is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.

Structure

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

1326
  Mrv0541 02231215232D          

 32 35  0  0  1  0            999 V2000
    5.8136   -0.8460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.3915    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9421    0.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    2.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546   -0.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    2.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1064   -2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    0.3915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9421   -1.0214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    0.4684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694    1.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.4335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3599   -0.4369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3599    0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7394   -0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    1.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3215   -1.3942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1189   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3341   -0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7011   -1.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1314   -0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4984   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136   -0.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6976   -1.0713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  2 25  1  0  0  0  0
  3 16  2  0  0  0  0
  4 22  1  0  0  0  0
  5 21  2  0  0  0  0
  6 22  2  0  0  0  0
 23  7  1  1  0  0  0
  8 14  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
 15  9  1  1  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 10 25  1  0  0  0  0
 10 31  1  0  0  0  0
 11 13  1  0  0  0  0
 11 25  2  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 14 32  1  6  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015421
     RDKit          3D
Cefamandole
 49 52  0  0  0  0  0  0  0  0999 V2000
   -6.9348   -1.6534    1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748   -0.8567    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7888   -0.8066   -0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9337    0.0099   -1.2049 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7761    0.4761   -1.5954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8123   -0.0698   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0830    0.2728   -0.9521 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0629   -0.6139    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -0.2465    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    0.2956    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6067    2.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.1344    3.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.3988    2.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    0.6489    0.9168 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.7412    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595    0.4976    2.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.2224    0.1713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.3536   -0.5050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    0.8351   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    2.0641   -0.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -0.0731   -1.7101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8263   -1.3451   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6751    0.0048   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6968    0.7133   -1.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9116    0.7829   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.1688    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0691   -0.5296    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.6181    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    1.2031   -0.3407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4547   -0.0257   -1.6010 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -0.6088   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -2.3156    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6620   -1.0428    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7432   -2.3403    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656   -1.7436   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -0.6038    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9903   -0.1885    3.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    2.2834    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778   -0.6470   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4481    0.3107   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -1.6633   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309    1.1976   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332    1.3253   -1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0552    0.2235    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748   -1.0262    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -1.1735    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    2.1852   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -0.0872   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -1.6897   -1.4728 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 14  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 17 38  1  1
 18 39  1  0
 21 40  1  6
 22 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
 27 45  1  0
 28 46  1  0
 29 47  1  6
 31 48  1  0
 31 49  1  0
M  END

1326
  Mrv0541 02231215232D          

 32 35  0  0  1  0            999 V2000
    5.8136   -0.8460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.3915    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9421    0.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    2.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546   -0.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    2.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1064   -2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    0.3915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9421   -1.0214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    0.4684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694    1.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.4335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3599   -0.4369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3599    0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7394   -0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    1.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3215   -1.3942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1189   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3341   -0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7011   -1.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1314   -0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4984   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7136   -0.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6976   -1.0713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  2 25  1  0  0  0  0
  3 16  2  0  0  0  0
  4 22  1  0  0  0  0
  5 21  2  0  0  0  0
  6 22  2  0  0  0  0
 23  7  1  1  0  0  0
  8 14  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
 15  9  1  1  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 10 25  1  0  0  0  0
 10 31  1  0  0  0  0
 11 13  1  0  0  0  0
 11 25  2  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 14 32  1  6  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015421

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

> <INCHI_KEY>
OLVCFLKTBJRLHI-AXAPSJFSSA-N

> <FORMULA>
C18H18N6O5S2

> <MOLECULAR_WEIGHT>
462.503

> <EXACT_MASS>
462.078009096

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
42.45169371935944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
0.02708561566666722

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.254702823526518

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3241952909495636

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7273081540177473

> <JCHEM_POLAR_SURFACE_AREA>
150.54000000000002

> <JCHEM_REFRACTIVITY>
126.6455

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cefamandole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015421
     RDKit          3D
Cefamandole
 49 52  0  0  0  0  0  0  0  0999 V2000
   -6.9348   -1.6534    1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748   -0.8567    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7888   -0.8066   -0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9337    0.0099   -1.2049 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7761    0.4761   -1.5954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8123   -0.0698   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0830    0.2728   -0.9521 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0629   -0.6139    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -0.2465    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    0.2956    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6067    2.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.1344    3.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.3988    2.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    0.6489    0.9168 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.7412    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595    0.4976    2.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.2224    0.1713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.3536   -0.5050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    0.8351   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    2.0641   -0.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -0.0731   -1.7101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8263   -1.3451   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6751    0.0048   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6968    0.7133   -1.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9116    0.7829   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.1688    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0691   -0.5296    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.6181    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    1.2031   -0.3407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4547   -0.0257   -1.6010 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -0.6088   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -2.3156    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6620   -1.0428    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7432   -2.3403    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656   -1.7436   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -0.6038    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9903   -0.1885    3.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    2.2834    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778   -0.6470   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4481    0.3107   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -1.6633   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309    1.1976   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332    1.3253   -1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0552    0.2235    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748   -1.0262    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -1.1735    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    2.1852   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -0.0872   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -1.6897   -1.4728 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 14  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 17 38  1  1
 18 39  1  0
 21 40  1  6
 22 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
 27 45  1  0
 28 46  1  0
 29 47  1  6
 31 48  1  0
 31 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1326                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      10.852  -1.579   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       6.851   0.731   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      14.825   1.828   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.519   3.811   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.715  -0.024   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.186   3.811   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      16.999  -4.089   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.186   0.731   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      14.825  -1.907   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.110   0.874   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.356   3.032   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.080   2.019   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.850   3.353   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      12.186  -0.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.738  -0.816   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.738   0.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.852   1.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.519   0.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.519  -0.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.185   1.501   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.314  -1.511   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.852   3.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.400  -2.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.889  -2.207   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.517   1.501   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.290  -0.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.975  -3.298   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.779  -0.325   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.464  -2.903   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.865  -1.416   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.790  -0.632   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      12.502  -2.000   0.000  0.00  0.00           H+0
CONECT    1   14   19                                                       
CONECT    2   20   25                                                       
CONECT    3   16                                                            
CONECT    4   22                                                            
CONECT    5   21                                                            
CONECT    6   22                                                            
CONECT    7   23                                                            
CONECT    8   14   16   17                                                  
CONECT    9   15   21                                                       
CONECT   10   12   25   31                                                  
CONECT   11   13   25                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
CONECT   14    1    8   15   32                                             
CONECT   15    9   14   16                                                  
CONECT   16    3    8   15                                                  
CONECT   17    8   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19    1   18                                                       
CONECT   20    2   18                                                       
CONECT   21    5    9   23                                                  
CONECT   22    4    6   17                                                  
CONECT   23    7   21   24                                                  
CONECT   24   23   26   27                                                  
CONECT   25    2   10   11                                                  
CONECT   26   24   28                                                       
CONECT   27   24   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   30                                                       
CONECT   30   28   29                                                       
CONECT   31   10                                                            
CONECT   32   14                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0015421
HETATM    1  C1  UNL     1      -6.935  -1.653   1.126  1.00  0.00           C  
HETATM    2  N1  UNL     1      -7.475  -0.857   0.066  1.00  0.00           N  
HETATM    3  N2  UNL     1      -8.789  -0.807  -0.193  1.00  0.00           N  
HETATM    4  N3  UNL     1      -8.934   0.010  -1.205  1.00  0.00           N  
HETATM    5  N4  UNL     1      -7.776   0.476  -1.595  1.00  0.00           N  
HETATM    6  C2  UNL     1      -6.812  -0.070  -0.788  1.00  0.00           C  
HETATM    7  S1  UNL     1      -5.083   0.273  -0.952  1.00  0.00           S  
HETATM    8  C3  UNL     1      -4.063  -0.614   0.224  1.00  0.00           C  
HETATM    9  C4  UNL     1      -2.628  -0.247   0.093  1.00  0.00           C  
HETATM   10  C5  UNL     1      -1.964   0.296   1.060  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.528   0.607   2.366  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.750   1.134   3.258  1.00  0.00           O  
HETATM   13  O2  UNL     1      -3.819   0.399   2.761  1.00  0.00           O  
HETATM   14  N5  UNL     1      -0.563   0.649   0.917  1.00  0.00           N  
HETATM   15  C7  UNL     1       0.755   0.741   1.440  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.259   0.498   2.578  1.00  0.00           O  
HETATM   17  C8  UNL     1       1.308   1.222   0.171  1.00  0.00           C  
HETATM   18  N6  UNL     1       2.218   0.354  -0.505  1.00  0.00           N  
HETATM   19  C9  UNL     1       3.436   0.835  -1.013  1.00  0.00           C  
HETATM   20  O4  UNL     1       3.703   2.064  -0.854  1.00  0.00           O  
HETATM   21  C10 UNL     1       4.369  -0.073  -1.710  1.00  0.00           C  
HETATM   22  O5  UNL     1       3.826  -1.345  -1.722  1.00  0.00           O  
HETATM   23  C11 UNL     1       5.675   0.005  -1.024  1.00  0.00           C  
HETATM   24  C12 UNL     1       6.697   0.713  -1.642  1.00  0.00           C  
HETATM   25  C13 UNL     1       7.912   0.783  -0.995  1.00  0.00           C  
HETATM   26  C14 UNL     1       8.087   0.169   0.213  1.00  0.00           C  
HETATM   27  C15 UNL     1       7.069  -0.530   0.815  1.00  0.00           C  
HETATM   28  C16 UNL     1       5.831  -0.618   0.187  1.00  0.00           C  
HETATM   29  C17 UNL     1      -0.115   1.203  -0.341  1.00  0.00           C  
HETATM   30  S2  UNL     1      -0.455  -0.026  -1.601  1.00  0.00           S  
HETATM   31  C18 UNL     1      -2.103  -0.609  -1.268  1.00  0.00           C  
HETATM   32  H1  UNL     1      -6.136  -2.316   0.794  1.00  0.00           H  
HETATM   33  H2  UNL     1      -6.662  -1.043   2.021  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.743  -2.340   1.535  1.00  0.00           H  
HETATM   35  H4  UNL     1      -4.066  -1.744  -0.073  1.00  0.00           H  
HETATM   36  H5  UNL     1      -4.508  -0.604   1.188  1.00  0.00           H  
HETATM   37  H6  UNL     1      -3.990  -0.189   3.571  1.00  0.00           H  
HETATM   38  H7  UNL     1       1.643   2.283   0.264  1.00  0.00           H  
HETATM   39  H8  UNL     1       1.978  -0.647  -0.624  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.448   0.311  -2.766  1.00  0.00           H  
HETATM   41  H10 UNL     1       3.730  -1.663  -0.800  1.00  0.00           H  
HETATM   42  H11 UNL     1       6.531   1.198  -2.612  1.00  0.00           H  
HETATM   43  H12 UNL     1       8.733   1.325  -1.442  1.00  0.00           H  
HETATM   44  H13 UNL     1       9.055   0.224   0.729  1.00  0.00           H  
HETATM   45  H14 UNL     1       7.175  -1.026   1.769  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.029  -1.173   0.673  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.513   2.185  -0.631  1.00  0.00           H  
HETATM   48  H17 UNL     1      -2.799  -0.087  -1.990  1.00  0.00           H  
HETATM   49  H18 UNL     1      -2.261  -1.690  -1.473  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    6
CONECT    3    4    4
CONECT    4    5
CONECT    5    6    6
CONECT    6    7
CONECT    7    8
CONECT    8    9   35   36
CONECT    9   10   10   31
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   13   37
CONECT   14   15   29
CONECT   15   16   16   17
CONECT   17   18   29   38
CONECT   18   19   39
CONECT   19   20   20   21
CONECT   21   22   23   40
CONECT   22   41
CONECT   23   24   24   28
CONECT   24   25   42
CONECT   25   26   26   43
CONECT   26   27   44
CONECT   27   28   28   45
CONECT   28   46
CONECT   29   30   47
CONECT   30   31
CONECT   31   48   49
END

HMDB0015421
     RDKit          3D
Cefamandole
 49 52  0  0  0  0  0  0  0  0999 V2000
   -6.9348   -1.6534    1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748   -0.8567    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7888   -0.8066   -0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9337    0.0099   -1.2049 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7761    0.4761   -1.5954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8123   -0.0698   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0830    0.2728   -0.9521 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0629   -0.6139    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -0.2465    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    0.2956    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    0.6067    2.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.1344    3.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.3988    2.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    0.6489    0.9168 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.7412    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595    0.4976    2.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.2224    0.1713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.3536   -0.5050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    0.8351   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    2.0641   -0.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -0.0731   -1.7101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8263   -1.3451   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6751    0.0048   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6968    0.7133   -1.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9116    0.7829   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.1688    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0691   -0.5296    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.6181    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    1.2031   -0.3407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4547   -0.0257   -1.6010 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -0.6088   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -2.3156    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6620   -1.0428    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7432   -2.3403    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656   -1.7436   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -0.6038    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9903   -0.1885    3.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    2.2834    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778   -0.6470   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4481    0.3107   -2.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -1.6633   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309    1.1976   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332    1.3253   -1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0552    0.2235    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748   -1.0262    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -1.1735    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    2.1852   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -0.0872   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -1.6897   -1.4728 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
  6  2  1  0
 31  9  1  0
 29 14  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 17 38  1  1
 18 39  1  0
 21 40  1  6
 22 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
 27 45  1  0
 28 46  1  0
 29 47  1  6
 31 48  1  0
 31 49  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid	ChEBI
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefadole	ChEBI
Cefamandol	ChEBI
Cefamandolum	ChEBI
Cephadole	ChEBI
Cephamandole	ChEBI
L-Cefamandole	ChEBI
CMD	Kegg
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylate	Generator
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Cefamandole nafate	HMDB
Compound 83405	HMDB

Chemical Formula

C₁₈H₁₈N₆O₅S₂

Average Molecular Weight

462.503

Monoisotopic Molecular Weight

462.078009096

IUPAC Name

(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefamandole

CAS Registry Number

34444-01-4

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

InChI Key

OLVCFLKTBJRLHI-AXAPSJFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Cephalosporin
N-acyl-alpha amino acid or derivatives
N-carbamoyl-alpha-amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Cephem
Piperazine-1-carboxamide
Dioxopiperazine
Aryl thioether
Alkylarylthioether
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
N-alkylpiperazine
Ureide
Phenol
Benzenoid
1,4-diazinane
Piperazine
Meta-thiazine
Monocyclic benzene moiety
Dicarboximide
Azole
Tertiary carboxylic acid amide
Tetrazole
Beta-lactam
Heteroaromatic compound
Azetidine
Urea
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carbonic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hemithioaminal
Sulfenyl compound
Thioether
Carboxylic acid
Dialkylthioether
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	0.58 g/L	Not Available
LogP	0.50	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.58 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	0.027	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.54 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.65 m³·mol⁻¹	ChemAxon
Polarizability	42.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.088	31661259
DarkChem	[M-H]-	190.048	31661259
DeepCCS	[M-2H]-	228.876	30932474
DeepCCS	[M+Na]+	205.238	30932474
AllCCS	[M+H]+	201.7	32859911
AllCCS	[M+H-H2O]+	199.7	32859911
AllCCS	[M+NH4]+	203.5	32859911
AllCCS	[M+Na]+	204.0	32859911
AllCCS	[M-H]-	193.3	32859911
AllCCS	[M+Na-2H]-	193.6	32859911
AllCCS	[M+HCOO]-	194.1	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.	3.6 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5256 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2109.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	210.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	303.2 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	440.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	859.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	393.4 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	1292.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	291.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	183.7 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	167.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cefamandole	[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O	4918.1	Standard polar	33892256
Cefamandole	[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O	2971.0	Standard non polar	33892256
Cefamandole	[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O	3916.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cefamandole,1TMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1	4059.7	Semi standard non polar	33892256
Cefamandole,1TMS,isomer #2	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](O)C3=CC=CC=C3)[C@H]2SC1	4064.0	Semi standard non polar	33892256
Cefamandole,1TMS,isomer #3	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](O)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3930.0	Semi standard non polar	33892256
Cefamandole,2TMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1	3945.3	Semi standard non polar	33892256
Cefamandole,2TMS,isomer #2	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3847.3	Semi standard non polar	33892256
Cefamandole,2TMS,isomer #3	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3824.5	Semi standard non polar	33892256
Cefamandole,3TMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3792.2	Semi standard non polar	33892256
Cefamandole,3TMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	3483.2	Standard non polar	33892256
Cefamandole,3TMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1	5199.6	Standard polar	33892256
Cefamandole,1TBDMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1	4249.1	Semi standard non polar	33892256
Cefamandole,1TBDMS,isomer #2	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](O)C3=CC=CC=C3)[C@H]2SC1	4277.9	Semi standard non polar	33892256
Cefamandole,1TBDMS,isomer #3	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](O)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4165.0	Semi standard non polar	33892256
Cefamandole,2TBDMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1	4353.7	Semi standard non polar	33892256
Cefamandole,2TBDMS,isomer #2	CN1N=NN=C1SCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4239.4	Semi standard non polar	33892256
Cefamandole,2TBDMS,isomer #3	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4255.5	Semi standard non polar	33892256
Cefamandole,3TBDMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4392.7	Semi standard non polar	33892256
Cefamandole,3TBDMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	4096.2	Standard non polar	33892256
Cefamandole,3TBDMS,isomer #1	CN1N=NN=C1SCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1	5311.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cefamandole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-171ae249ec803b8d5abd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefamandole GC-MS (2 TMS) - 70eV, Positive	splash10-004i-0900000000-fb3cc081c83b0d53a10c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cefamandole 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 - Cefamandole 10V, Positive-QTOF	splash10-05dl-4698600000-8b8ba1529bcdbe274bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 20V, Positive-QTOF	splash10-0ab9-4956100000-2107c26a4908fb9913eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 40V, Positive-QTOF	splash10-05fr-3390000000-2cd8861a785705076af0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 10V, Negative-QTOF	splash10-014l-1910200000-8214388978bd4c2b1ca7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 20V, Negative-QTOF	splash10-0aor-9710000000-6d5c2f7837d35a1fb4fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 40V, Negative-QTOF	splash10-0ar3-9530000000-32e2979223057f6e2cf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 10V, Positive-QTOF	splash10-03dj-0115900000-a9a6c926ad8c4264e63c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 20V, Positive-QTOF	splash10-00dj-2985600000-bc5faa5980b8da2874ea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 40V, Positive-QTOF	splash10-0007-9671200000-347a700c832c4adbf8db	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 10V, Negative-QTOF	splash10-004i-0100900000-40b310ffa3cee38ef34c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 20V, Negative-QTOF	splash10-0300-3952500000-b7a5de24cc9eeb2c9ab0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cefamandole 40V, Negative-QTOF	splash10-066r-9710300000-07002f5735b982b36a8d	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB01326	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01326	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01326

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

401748

KEGG Compound ID

C06879

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefamandole

METLIN ID

Not Available

PubChem Compound

456255

PDB ID

SMX

ChEBI ID

3480

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

Not Available

Transporters

Enzyme Details

1. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]

Enzyme Details

2. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172 ]
Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

Enzyme Details

3. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [PubMed:12650826 ]

Showing metabocard for Cefamandole (HMDB0015421)

MOL for HMDB0015421 (Cefamandole)

3D MOL for HMDB0015421 (Cefamandole)

3D SDF for HMDB0015421 (Cefamandole)

3D-SDF for HMDB0015421 (Cefamandole)

PDB for HMDB0015421 (Cefamandole)

3D PDB for HMDB0015421 (Cefamandole)

SMILES for HMDB0015421 (Cefamandole)

INCHI for HMDB0015421 (Cefamandole)

Structure for HMDB0015421 (Cefamandole)

3D Structure for HMDB0015421 (Cefamandole)

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

References