Showing metabocard for 2-Keto-6-aminocaproate (MMDBc0047966)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:19:30 UTC
Update Date2022-09-01 02:13:40 UTC
Metabolite IDMMDBc0047966
Metabolite Identification
Common Name2-Keto-6-aminocaproate
Description2-Keto-6-aminocaproate is an intermediate in lysine degradation and can be formed from L-lysine. L-Lysine is an essential amino-acid that is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. L-Lysine can be converted to 2-keto-6-aminocaproate via the enzyme L-lysine alpha-oxidase. 2-Keto-6-aminocaproate can spontaneously decarboxylate to 5-aminovalerate in the presence of the reaction product, hydrogen peroxide. It can also be spontaneously converted in solution to its cyclic form delta-piperideine-2-carboxylate. This has been demonstrated in vitro in the presence of catalase, which splits hydrogen peroxide.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5a840f6e10>


  Mrv0541 02241203472D          

 10  9  0  0  0  0            999 V2000
   11.2296  -10.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5151  -10.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9441  -10.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8007  -10.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6585  -10.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727  -10.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862  -10.3907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6585  -11.6279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0872  -10.8032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727   -9.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5a840f6e10>

HMDB0012151
     RDKit          3D
2-Keto-6-aminocaproate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.6242    0.5284    0.7765 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    0.7189    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -0.3429    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -0.0389   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.0683   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -0.6856   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -0.9004   -2.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360   -0.0752   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610    0.1643    1.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.2850   -0.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    1.1602    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4267    0.5477    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.8233   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599    1.7064    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7775   -1.3123    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.4339    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.9536    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855   -0.0059   -1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709   -2.0872   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641   -1.0395    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    1.1025   -1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
 10 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f5a840f6e10>


  Mrv0541 02241203472D          

 10  9  0  0  0  0            999 V2000
   11.2296  -10.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5151  -10.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9441  -10.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8007  -10.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6585  -10.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727  -10.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862  -10.3907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6585  -11.6279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0872  -10.8032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727   -9.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047966

> <DATABASE_NAME>
MIME

> <SMILES>
NCCCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3/c7-4-2-1-3-5(8)6(9)10/h1-4,7H2,(H,9,10)

> <INCHI_KEY>
GWENQMVPLJAMAE-UHFFFAOYSA-N

> <FORMULA>
C6H11NO3

> <MOLECULAR_WEIGHT>
145.1564

> <EXACT_MASS>
145.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.618438282127595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-2-oxohexanoic acid

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-2.151053014118317

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2413405203245573

> <JCHEM_PKA_STRONGEST_BASIC>
10.005116205021158

> <JCHEM_POLAR_SURFACE_AREA>
80.39000000000001

> <JCHEM_REFRACTIVITY>
35.4048

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-2-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f5a840f6e10>

HMDB0012151
     RDKit          3D
2-Keto-6-aminocaproate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.6242    0.5284    0.7765 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    0.7189    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -0.3429    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -0.0389   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.0683   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -0.6856   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -0.9004   -2.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360   -0.0752   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610    0.1643    1.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.2850   -0.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    1.1602    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4267    0.5477    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.8233   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599    1.7064    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7775   -1.3123    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.4339    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.9536    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855   -0.0059   -1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709   -2.0872   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641   -1.0395    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    1.1025   -1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
 10 21  1  0
M  END
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PDB for #<Metabolite:0x00007f5a840f6e10>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      20.962 -20.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.628 -19.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.296 -19.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.295 -20.166   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.629 -20.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.962 -19.396   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      16.961 -19.396   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      23.629 -21.705   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      26.296 -20.166   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      24.962 -17.856   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8    6                                                  
CONECT    6    5    9   10                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f5a840f6e10>

COMPND    HMDB0012151
HETATM    1  N1  UNL     1       3.624   0.528   0.776  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.373   0.719   0.117  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.348  -0.343   0.452  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.067  -0.039  -0.299  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.000  -1.068  -0.005  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.200  -0.686  -0.776  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.223  -0.900  -2.006  1.00  0.00           O  
HETATM    8  C6  UNL     1      -3.336  -0.075  -0.151  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.361   0.164   1.095  1.00  0.00           O  
HETATM   10  O3  UNL     1      -4.464   0.285  -0.871  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.775   1.160   1.588  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.427   0.548   0.105  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.523   0.823  -0.968  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.960   1.706   0.469  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.777  -1.312   0.101  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.203  -0.434   1.531  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.310   0.954   0.043  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.285  -0.006  -1.375  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.671  -2.087  -0.277  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.264  -1.039   1.073  1.00  0.00           H  
HETATM   21  H11 UNL     1      -4.532   1.103  -1.425  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    7    8
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for #<Metabolite:0x00007f5a840f6e10>

NCCCCC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007f5a840f6e10>

InChI=1S/C6H11NO3/c7-4-2-1-3-5(8)6(9)10/h1-4,7H2,(H,9,10)
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Synonyms
ValueSource
2-oxo-6-AminocaproateChEBI
6-Amino-2-oxohexanoateChEBI
2-oxo-6-Aminocaproic acidGenerator
6-Amino-2-oxohexanoic acidGenerator
2-Keto-6-aminocaproic acidGenerator
2-keto-6-amino-CaproateHMDB
2-keto-6-amino-Caproic acidHMDB
2-oxo-6-AminohexanoateHMDB
2-oxo-6-Aminohexanoic acidHMDB
alpha-keto-epsilon-AminocaproateHMDB
alpha-keto-epsilon-Aminocaproic acidHMDB
alpha-keto-epsilon-AminohexanoateHMDB
alpha-keto-epsilon-Aminohexanoic acidHMDB
alpha-KetolysineHMDB
Molecular FormulaC6H11NO3
Average Mass145.1564
Monoisotopic Mass145.073893223
IUPAC Name6-amino-2-oxohexanoic acid
Traditional Name6-amino-2-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
NCCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c7-4-2-1-3-5(8)6(9)10/h1-4,7H2,(H,9,10)
InChI KeyGWENQMVPLJAMAE-UHFFFAOYSA-N