NP-MRD: Showing NP-Card for (6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0314790)

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Record Information

Version

2.0

Created at

2022-09-11 13:05:07 UTC

Updated at

2022-09-11 13:05:08 UTC

NP-MRD ID

NP0314790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

Cefamandole, also known as cefadole or CMD, 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. Cefamandole is a drug which is used for the treatment of serious infections caused by susceptible strains of microorganisms. Cefamandole is an extremely weak basic (essentially neutral) compound (based on its pKa). (6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. (6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was first documented in 1974 (PMID: 15828189). A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups.

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    2.5743   -2.1023    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515   -1.8638    0.4763 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6799   -2.6249   -0.3388 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -2.1464   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974   -1.0789    0.3749 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595   -0.9113    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781    0.4015    2.0311 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8196    1.8508    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944    1.4790    0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3257    1.4229   -0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237    1.5416   -1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    1.4937   -3.0330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394    1.7068   -1.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    1.1499   -1.4365 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280    0.4615   -2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6156   -0.2865   -3.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9201    0.9716   -1.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8182    0.0158   -1.2925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1742    0.0115   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.8399   -2.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1684   -0.9488   -1.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4317   -0.7439   -1.6861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -0.8747    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8757    0.1173    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952    0.1714    2.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -0.7832    3.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -1.7801    2.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5459   -1.8122    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    1.7967   -0.9003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2117    1.2929    0.8164 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353    1.2668    1.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.0867    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8931   -1.3510    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062   -2.1242    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786    2.6908    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5367    2.2941    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3260    2.4008   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    1.6512   -2.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.6824   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -2.0040   -1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1271   -0.9860   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3928    0.8577    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4291    0.9566    2.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2251   -0.7677    4.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048   -2.5617    3.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0004   -2.6134    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.8952   -1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5349    2.0808    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    0.3151    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 30 31  1  0
 31  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  9 10  2  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
 10 11  1  0
 11 13  1  0
 11 12  2  0
 14 29  1  0
 28 23  1  0
 17 29  1  0
  2  6  1  0
 29 47  1  1
 31 48  1  0
 31 49  1  0
  8 35  1  0
  8 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 17 38  1  6
 18 39  1  0
 21 40  1  1
 22 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
 27 45  1  0
 28 46  1  0
 13 37  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>
NP0314790

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

462.5030 Da

Monoisotopic Mass

462.07801 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.05	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

External Links

HMDB ID

HMDB0015421

DrugBank ID

DB01326

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Neu HC: Cefamandole, a cephalosporin antibiotic with an unusually wide spectrum of activity. Antimicrob Agents Chemother. 1974 Aug;6(2):177-82. doi: 10.1128/AAC.6.2.177. [PubMed:15828189 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0314790)

MOL for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0314790 ((6r,7r)-7-{[(2r)-1,2-dihydroxy-2-phenylethylidene]amino}-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)