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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:14:33 UTC

Update Date

2021-10-01 18:58:07 UTC

HMDB ID

HMDB0247232

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7-Aminocephalosporanic acid

Description

7-Aminocephalosporanic acid belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on 7-Aminocephalosporanic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 7-aminocephalosporanic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 7-Aminocephalosporanic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247232
     RDKit          3D
7-Aminocephalosporanic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.6538   -0.8654    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.7723    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -1.7565   -0.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.3947    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    0.8103   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    0.2402   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.0517    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    2.5006    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    3.2158    0.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    3.2684    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9198    0.5562    0.3250 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3205    0.7963    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0598    1.7923   -0.0074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186   -0.5740    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -1.4539   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -0.7892    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -1.8803   -0.3715 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.2258   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6099   -1.8591    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -0.0389    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232   -0.8350    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.8634   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.3512   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554    4.0867   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713   -0.5527    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -2.3717   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -1.7163    0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -0.9590    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -1.6568    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -1.6208   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
 10 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
M  END

  Mrv1652309112102142D          

 18 19  0  0  0  0            999 V2000
    4.8503    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635    0.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2615    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2615    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    0.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    2.3843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    2.2135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247232

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC1=C(N2C(SC1)C(N)C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)

> <INCHI_KEY>
HSHGZXNAXBPPDL-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O5S

> <MOLECULAR_WEIGHT>
272.28

> <EXACT_MASS>
272.046692668

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.695335980637005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-3.8148884752885754

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.621162092024626

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4190428887385216

> <JCHEM_PKA_STRONGEST_BASIC>
7.385654668675919

> <JCHEM_POLAR_SURFACE_AREA>
109.92999999999999

> <JCHEM_REFRACTIVITY>
62.738400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-aminocephalosporanic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247232
     RDKit          3D
7-Aminocephalosporanic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.6538   -0.8654    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.7723    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -1.7565   -0.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.3947    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    0.8103   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    0.2402   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.0517    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    2.5006    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    3.2158    0.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    3.2684    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9198    0.5562    0.3250 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3205    0.7963    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0598    1.7923   -0.0074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186   -0.5740    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -1.4539   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -0.7892    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -1.8803   -0.3715 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.2258   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6099   -1.8591    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -0.0389    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232   -0.8350    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.8634   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.3512   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554    4.0867   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713   -0.5527    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -2.3717   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -1.7163    0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -0.9590    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -1.6568    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -1.6208   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
 10 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       9.054   1.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.720   1.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.720  -0.488   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.387   1.822   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.053   1.052   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.719   1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.386   1.052   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.052   1.822   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.052   3.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.488   3.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.488   1.822   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.577   0.733   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -1.577   4.451   0.000  0.00  0.00           N+0
HETATM   14  S   UNK     0       2.386   4.132   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       3.719   3.362   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.386  -0.488   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.052  -1.258   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.719  -1.258   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    8   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    9   15                                                       
CONECT   15   14    6                                                       
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0247232
HETATM    1  C1  UNL     1       4.654  -0.865   1.068  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.497  -0.772   0.107  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.219  -1.757  -0.605  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.807   0.395   0.064  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.714   0.810  -0.661  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.384   0.240  -0.349  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.590   1.052   0.045  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.448   2.501   0.207  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.459   3.216   0.583  1.00  0.00           O  
HETATM   10  O4  UNL     1       0.665   3.268   0.012  1.00  0.00           O  
HETATM   11  N1  UNL     1      -1.920   0.556   0.325  1.00  0.00           N  
HETATM   12  C7  UNL     1      -3.321   0.796   0.301  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.060   1.792  -0.007  1.00  0.00           O  
HETATM   14  C8  UNL     1      -3.619  -0.574   0.778  1.00  0.00           C  
HETATM   15  N2  UNL     1      -4.232  -1.454  -0.172  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.151  -0.789   0.878  1.00  0.00           C  
HETATM   17  S1  UNL     1      -1.404  -1.880  -0.371  1.00  0.00           S  
HETATM   18  C10 UNL     1       0.293  -1.226  -0.519  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.610  -1.859   1.583  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.624  -0.039   1.807  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.623  -0.835   0.541  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.760   1.863  -0.899  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.936   0.351  -1.745  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.755   4.087  -0.537  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.171  -0.553   1.756  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.696  -2.372  -0.208  1.00  0.00           H  
HETATM   27  H9  UNL     1      -5.224  -1.716   0.107  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.810  -0.959   1.891  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.856  -1.657   0.368  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.708  -1.621  -1.437  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   23
CONECT    6    7    7   18
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   24
CONECT   11   12   16
CONECT   12   13   13   14
CONECT   14   15   16   25
CONECT   15   26   27
CONECT   16   17   28
CONECT   17   18
CONECT   18   29   30
END

HMDB0247232
     RDKit          3D
7-Aminocephalosporanic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.6538   -0.8654    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.7723    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -1.7565   -0.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    0.3947    0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    0.8103   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    0.2402   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.0517    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    2.5006    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    3.2158    0.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    3.2684    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9198    0.5562    0.3250 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3205    0.7963    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0598    1.7923   -0.0074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6186   -0.5740    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -1.4539   -0.1723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -0.7892    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -1.8803   -0.3715 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.2258   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6099   -1.8591    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -0.0389    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232   -0.8350    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.8634   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.3512   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554    4.0867   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713   -0.5527    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -2.3717   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2244   -1.7163    0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -0.9590    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -1.6568    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -1.6208   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  6  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
 10 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
 18 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
7-Aminocephalosporanate	Generator

Chemical Formula

C₁₀H₁₂N₂O₅S

Average Molecular Weight

272.28

Monoisotopic Molecular Weight

272.046692668

IUPAC Name

3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

7-aminocephalosporanic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C(N2C(SC1)C(N)C2=O)C(O)=O

InChI Identifier

InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)

InChI Key

HSHGZXNAXBPPDL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Cephem
Meta-thiazine
Dicarboxylic acid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Azetidine
Amino acid
Carboxamide group
Carboxylic acid ester
Lactam
Azacycle
Carboxylic acid
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1	ALOGPS
logP	-3.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	7.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.74 m³·mol⁻¹	ChemAxon
Polarizability	25.7 Å³	ChemAxon
Number of Rings	2	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]+	152.906	30932474
DeepCCS	[M-H]-	150.548	30932474
DeepCCS	[M-2H]-	183.532	30932474
DeepCCS	[M+Na]+	158.999	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	153.4	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.7	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.4	32859911
AllCCS	[M+HCOO]-	157.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Aminocephalosporanic acid	CC(=O)OCC1=C(N2C(SC1)C(N)C2=O)C(O)=O	3590.3	Standard polar	33892256
7-Aminocephalosporanic acid	CC(=O)OCC1=C(N2C(SC1)C(N)C2=O)C(O)=O	2012.0	Standard non polar	33892256
7-Aminocephalosporanic acid	CC(=O)OCC1=C(N2C(SC1)C(N)C2=O)C(O)=O	2329.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Aminocephalosporanic acid,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N[Si](C)(C)C)C2SC1	2330.2	Semi standard non polar	33892256
7-Aminocephalosporanic acid,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N[Si](C)(C)C)C2SC1	2212.9	Standard non polar	33892256
7-Aminocephalosporanic acid,2TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N[Si](C)(C)C)C2SC1	3778.8	Standard polar	33892256
7-Aminocephalosporanic acid,2TMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	2361.2	Semi standard non polar	33892256
7-Aminocephalosporanic acid,2TMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	2320.9	Standard non polar	33892256
7-Aminocephalosporanic acid,2TMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	3518.8	Standard polar	33892256
7-Aminocephalosporanic acid,3TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	2383.7	Semi standard non polar	33892256
7-Aminocephalosporanic acid,3TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	2384.0	Standard non polar	33892256
7-Aminocephalosporanic acid,3TMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N([Si](C)(C)C)[Si](C)(C)C)C2SC1	3301.0	Standard polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N[Si](C)(C)C(C)(C)C)C2SC1	2708.3	Semi standard non polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N[Si](C)(C)C(C)(C)C)C2SC1	2667.7	Standard non polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N[Si](C)(C)C(C)(C)C)C2SC1	3758.8	Standard polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	2782.5	Semi standard non polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	2757.0	Standard non polar	33892256
7-Aminocephalosporanic acid,2TBDMS,isomer #2	CC(=O)OCC1=C(C(=O)O)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	3505.8	Standard polar	33892256
7-Aminocephalosporanic acid,3TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	3008.4	Semi standard non polar	33892256
7-Aminocephalosporanic acid,3TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	3010.0	Standard non polar	33892256
7-Aminocephalosporanic acid,3TBDMS,isomer #1	CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2SC1	3428.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9130000000-cdfcac15e848cd4c05e4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Aminocephalosporanic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 7-Aminocephalosporanic acid 10V, Positive-QTOF	splash10-00di-0090000000-4e4f6715f7ed22209ec3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Aminocephalosporanic acid 20V, Positive-QTOF	splash10-096r-0790000000-930531e60c1eafa509e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Aminocephalosporanic acid 40V, Positive-QTOF	splash10-053i-1910000000-21a667b119a5b3d820f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Aminocephalosporanic acid 10V, Negative-QTOF	splash10-01b9-0980000000-9d265ac4d7973611f739	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Aminocephalosporanic acid 20V, Negative-QTOF	splash10-0a4l-5390000000-0425ebaabcafa98dfad3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Aminocephalosporanic acid 40V, Negative-QTOF	splash10-0a4i-9330000000-1336bbe791250fa614d4	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13729

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Putative beta-lactamase HcpE

General function:: Not Available
Specific function:: May hydrolyze 6-aminopenicillinic acid and 7-aminocephalosporanic acid (ACA) derivatives.
Gene Name:: HCPE
Uniprot ID:: Q9ZMJ9
Molecular weight:: 39319.52

Enzyme Details

2. Acetyltransferase CD1211

General function:: Not Available
Specific function:: Catalyzes the transfer of an acetyl group from acetyl coenzyme A (AcCoA) to an acceptor substrate and releases both CoA and the acetylated product. It prefers L-threonine, L-serine and L-methionine. It can also use O-acetyl-L-serine, L-tryptophan, L-isoleucine, L-valine, L-homoserine, 7-aminocephalosporanic acid, thiamine pyrophosphate and thiamine.
Gene Name:: (GENBANK) PUTATIVE N-ACETYLTRANSFERASE
Uniprot ID:: Q18B70
Molecular weight:: 18435.26

Enzyme Details

3. Beta-lactamase HcpA

General function:: Not Available
Specific function:: Slowly hydrolyzes 6-aminopenicillinic acid and 7-aminocephalosporanic acid (ACA) derivatives. May be involved in the synthesis of the cell wall peptidoglycan (By similarity).
Gene Name:: HCPA
Uniprot ID:: Q9ZMM1
Molecular weight:: 27294.315

Enzyme Details

4. Beta-lactamase HcpB

General function:: Not Available
Specific function:: Hydrolyzes 6-aminopenicillinic acid and 7-aminocephalosporanic acid (ACA) derivatives.
Gene Name:: HCPB
Uniprot ID:: O25103
Molecular weight:: 15345.615

Enzyme Details

5. Putative beta-lactamase HcpD

General function:: Not Available
Specific function:: May hydrolyze 6-aminopenicillinic acid and 7-aminocephalosporanic acid (ACA) derivatives. Binds to penicillin (By similarity).
Gene Name:: HCPD
Uniprot ID:: Q9ZMS0
Molecular weight:: 33806.53

Enzyme Details

6. Putative beta-lactamase HcpC

General function:: Not Available
Specific function:: May hydrolyze 6-aminopenicillinic acid and 7-aminocephalosporanic acid (ACA) derivatives.
Gene Name:: HCPC
Uniprot ID:: Q9ZKB5
Molecular weight:: 31526.735

Showing metabocard for 7-Aminocephalosporanic acid (HMDB0247232)

MOL for HMDB0247232 (7-Aminocephalosporanic acid)

3D MOL for HMDB0247232 (7-Aminocephalosporanic acid)

3D SDF for HMDB0247232 (7-Aminocephalosporanic acid)

3D-SDF for HMDB0247232 (7-Aminocephalosporanic acid)

PDB for HMDB0247232 (7-Aminocephalosporanic acid)

3D PDB for HMDB0247232 (7-Aminocephalosporanic acid)

SMILES for HMDB0247232 (7-Aminocephalosporanic acid)

INCHI for HMDB0247232 (7-Aminocephalosporanic acid)

Structure for HMDB0247232 (7-Aminocephalosporanic acid)

3D Structure for HMDB0247232 (7-Aminocephalosporanic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes