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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:50:22 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254503

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metampicillin

Description

Metampicillin belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1]. Based on a literature review a small amount of articles have been published on Metampicillin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Metampicillin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metampicillin 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

HMDB0254503
     RDKit          3D
metampicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.6211   -0.2423    4.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -0.3595    2.8166 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3402    1.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939   -0.1391    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437   -1.0332    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.3959    0.9566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584   -0.0561    0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    1.1223    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.1131    1.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    0.7133   -0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -0.2676   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.7397   -0.7344 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228   -0.8333   -1.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520   -1.0652   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -1.3298   -2.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208    0.5887   -1.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.4804   -1.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.5323   -2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450    2.2997   -0.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356    0.1762    0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946    1.2435   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4871    1.1486   -1.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9578   -0.0690   -2.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148   -1.1566   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -1.0373    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -0.7986    4.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.3868    4.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4378    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    1.1451    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.8343    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295   -0.0449   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245   -0.7347   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9631   -2.1733   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -0.5422    0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8402   -1.6262   -3.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774   -0.6342   -3.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365   -2.2647   -2.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.7774   -2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    2.0364    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.2128   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756    2.0170   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315   -0.1831   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911   -2.1072   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8951    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 11  7  1  0
 25 20  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
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 16 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
M  END

  Mrv1652309112115502D          

 25 27  0  0  0  0            999 V2000
   -0.8256   -0.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2001    0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193    0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700    1.4707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4299    0.4333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    2.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    2.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    2.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    2.4665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    3.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    3.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    3.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    4.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    4.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    5.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    6.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8838    5.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8838    4.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8838    3.2915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8838    2.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432    0.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177    0.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9925    1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -0.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254503

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)SC2C(NC(=O)C(N=C)C3=CC=CC=C3)C(=O)N2C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)

> <INCHI_KEY>
FZECHKJQHUVANE-UHFFFAOYSA-N

> <FORMULA>
C17H19N3O4S

> <MOLECULAR_WEIGHT>
361.42

> <EXACT_MASS>
361.109627278

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25691368215553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3-dimethyl-6-[2-(methylideneamino)-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
-0.377170084032125

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.852923152727355

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2358142120767246

> <JCHEM_PKA_STRONGEST_BASIC>
4.144011801592737

> <JCHEM_POLAR_SURFACE_AREA>
99.07000000000001

> <JCHEM_REFRACTIVITY>
90.8655

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metampicillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254503
     RDKit          3D
metampicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.6211   -0.2423    4.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -0.3595    2.8166 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3402    1.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939   -0.1391    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437   -1.0332    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.3959    0.9566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584   -0.0561    0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    1.1223    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.1131    1.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    0.7133   -0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -0.2676   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.7397   -0.7344 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228   -0.8333   -1.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520   -1.0652   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -1.3298   -2.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208    0.5887   -1.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.4804   -1.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.5323   -2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450    2.2997   -0.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356    0.1762    0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946    1.2435   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4871    1.1486   -1.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9578   -0.0690   -2.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148   -1.1566   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -1.0373    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -0.7986    4.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.3868    4.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4378    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    1.1451    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.8343    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295   -0.0449   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245   -0.7347   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9631   -2.1733   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -0.5422    0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8402   -1.6262   -3.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774   -0.6342   -3.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365   -2.2647   -2.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.7774   -2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    2.0364    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.2128   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756    2.0170   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315   -0.1831   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911   -2.1072   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8951    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 11  7  1  0
 25 20  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  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      -1.541  -1.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.240   0.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.209   1.454   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.371   2.745   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.883   2.347   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      -0.803   0.809   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      -0.485   3.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.972   4.233   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.742   5.566   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.849   4.604   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.849   6.144   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.485   6.914   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.183   6.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.183   8.454   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.849   9.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.849  10.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.183  11.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.517  10.764   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.517   9.224   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       3.517   6.144   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.517   4.604   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.747   1.373   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.446   0.001   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.586   2.665   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.532  -0.582   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   25                                             
CONECT    3    2    4   22                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0254503
HETATM    1  C1  UNL     1       3.621  -0.242   4.057  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.872  -0.360   2.817  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.088   0.340   1.824  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.694  -0.139   1.837  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.344  -1.033   2.640  1.00  0.00           O  
HETATM    6  N2  UNL     1       0.742   0.396   0.957  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.658  -0.056   0.940  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.563   1.122   0.907  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.701   2.113   1.664  1.00  0.00           O  
HETATM   10  N3  UNL     1      -2.211   0.713  -0.292  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.123  -0.268  -0.473  1.00  0.00           C  
HETATM   12  S1  UNL     1      -2.182  -1.740  -0.734  1.00  0.00           S  
HETATM   13  C7  UNL     1      -3.623  -0.833  -1.426  1.00  0.00           C  
HETATM   14  C8  UNL     1      -4.852  -1.065  -0.620  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.830  -1.330  -2.836  1.00  0.00           C  
HETATM   16  C10 UNL     1      -3.121   0.589  -1.383  1.00  0.00           C  
HETATM   17  C11 UNL     1      -4.271   1.480  -1.237  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.189   1.532  -2.078  1.00  0.00           O  
HETATM   19  O4  UNL     1      -4.345   2.300  -0.120  1.00  0.00           O  
HETATM   20  C12 UNL     1       3.736   0.176   0.502  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.895   1.243  -0.354  1.00  0.00           C  
HETATM   22  C14 UNL     1       4.487   1.149  -1.591  1.00  0.00           C  
HETATM   23  C15 UNL     1       4.958  -0.069  -2.027  1.00  0.00           C  
HETATM   24  C16 UNL     1       4.815  -1.157  -1.196  1.00  0.00           C  
HETATM   25  C17 UNL     1       4.219  -1.037   0.036  1.00  0.00           C  
HETATM   26  H1  UNL     1       4.252  -0.799   4.754  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.815   0.387   4.367  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.152   1.438   2.075  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.052   1.145   0.290  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.887  -0.834   1.663  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.429  -0.045  -1.279  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.724  -0.735  -1.230  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.963  -2.173  -0.487  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.863  -0.542   0.350  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.840  -1.626  -3.232  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.377  -0.634  -3.474  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.437  -2.265  -2.781  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.608   0.777  -2.347  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.789   2.036   0.740  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.530   2.213  -0.030  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.576   2.017  -2.200  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.431  -0.183  -2.998  1.00  0.00           H  
HETATM   43  H18 UNL     1       5.191  -2.107  -1.555  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.117  -1.895   0.669  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3
CONECT    3    4   20   28
CONECT    4    5    5    6
CONECT    6    7   29
CONECT    7    8   11   30
CONECT    8    9    9   10
CONECT   10   11   16
CONECT   11   12   31
CONECT   12   13
CONECT   13   14   15   16
CONECT   14   32   33   34
CONECT   15   35   36   37
CONECT   16   17   38
CONECT   17   18   18   19
CONECT   19   39
CONECT   20   21   21   25
CONECT   21   22   40
CONECT   22   23   23   41
CONECT   23   24   42
CONECT   24   25   25   43
CONECT   25   44
END

HMDB0254503
     RDKit          3D
metampicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.6211   -0.2423    4.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -0.3595    2.8166 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3402    1.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939   -0.1391    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437   -1.0332    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.3959    0.9566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584   -0.0561    0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    1.1223    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    2.1131    1.6637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    0.7133   -0.2919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -0.2676   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.7397   -0.7344 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228   -0.8333   -1.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8520   -1.0652   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -1.3298   -2.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208    0.5887   -1.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.4804   -1.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890    1.5323   -2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450    2.2997   -0.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356    0.1762    0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946    1.2435   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4871    1.1486   -1.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9578   -0.0690   -2.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148   -1.1566   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -1.0373    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -0.7986    4.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.3868    4.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4378    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    1.1451    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.8343    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295   -0.0449   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245   -0.7347   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9631   -2.1733   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8628   -0.5422    0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8402   -1.6262   -3.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774   -0.6342   -3.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365   -2.2647   -2.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.7774   -2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7889    2.0364    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.2128   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756    2.0170   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315   -0.1831   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911   -2.1072   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8951    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 11  7  1  0
 25 20  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-{[1-hydroxy-2-(methylideneamino)-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	HMDB

Chemical Formula

C₁₇H₁₉N₃O₄S

Average Molecular Weight

361.42

Monoisotopic Molecular Weight

361.109627278

IUPAC Name

3,3-dimethyl-6-[2-(methylideneamino)-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

metampicillin

CAS Registry Number

Not Available

SMILES

CC1(C)SC2C(NC(=O)C(N=C)C3=CC=CC=C3)C(=O)N2C1C(O)=O

InChI Identifier

InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)

InChI Key

FZECHKJQHUVANE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hemithioaminal
Thioether
Imine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.74	ALOGPS
logP	-0.38	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	4.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.87 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	187.391	30932474
DeepCCS	[M-H]-	185.01	30932474
DeepCCS	[M-2H]-	219.507	30932474
DeepCCS	[M+Na]+	195.798	30932474
AllCCS	[M+H]+	181.8	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.3	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	182.2	32859911
AllCCS	[M+Na-2H]-	182.2	32859911
AllCCS	[M+HCOO]-	182.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
metampicillin	CC1(C)SC2C(NC(=O)C(N=C)C3=CC=CC=C3)C(=O)N2C1C(O)=O	3438.9	Standard polar	33892256
metampicillin	CC1(C)SC2C(NC(=O)C(N=C)C3=CC=CC=C3)C(=O)N2C1C(O)=O	2266.1	Standard non polar	33892256
metampicillin	CC1(C)SC2C(NC(=O)C(N=C)C3=CC=CC=C3)C(=O)N2C1C(O)=O	2908.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
metampicillin,2TMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2611.7	Semi standard non polar	33892256
metampicillin,2TMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2637.0	Standard non polar	33892256
metampicillin,2TMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	3398.4	Standard polar	33892256
metampicillin,2TBDMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3021.0	Semi standard non polar	33892256
metampicillin,2TBDMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3039.2	Standard non polar	33892256
metampicillin,2TBDMS,isomer #1	C=NC(C(=O)N(C1C(=O)N2C1SC(C)(C)C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3577.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1910000000-c32acb60183a760d31d7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metampicillin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Metampicillin 10V, Positive-QTOF	splash10-03di-0912000000-3632921e7be01527f801	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metampicillin 20V, Positive-QTOF	splash10-02tc-3901000000-b29b15ed29cab3ede2a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metampicillin 40V, Positive-QTOF	splash10-02tc-6900000000-d9d7845c5986442bbf48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metampicillin 10V, Negative-QTOF	splash10-014i-0094000000-f1c5f208b48f3f9a6771	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metampicillin 20V, Negative-QTOF	splash10-014i-8697000000-ecf013c603c1d0b26b89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metampicillin 40V, Negative-QTOF	splash10-0006-9210000000-dd99486b2a7b6037e607	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)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

3942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metampicillin

METLIN ID

Not Available

PubChem Compound

4084

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 ]

Showing metabocard for Metampicillin (HMDB0254503)

MOL for HMDB0254503 (Metampicillin)

3D MOL for HMDB0254503 (Metampicillin)

3D SDF for HMDB0254503 (Metampicillin)

3D-SDF for HMDB0254503 (Metampicillin)

PDB for HMDB0254503 (Metampicillin)

3D PDB for HMDB0254503 (Metampicillin)

SMILES for HMDB0254503 (Metampicillin)

INCHI for HMDB0254503 (Metampicillin)

Structure for HMDB0254503 (Metampicillin)

3D Structure for HMDB0254503 (Metampicillin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra