Showing metabocard for 3-Oxoadipic acid (MMDBc0047910)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:14:31 UTC
Update Date2024-04-30 20:32:16 UTC
Metabolite IDMMDBc0047910
Metabolite Identification
Common Name3-Oxoadipic acid
Description3-Oxoadipic acid is a regularly occurring Adipic dicarboxylic acid human metabolite found occasionally in biofluids of healthy individuals. (PMIDs 8340451, 1769109, 2338430) Increased amounts of 3-Oxoadipic acid are excreted after ingestion of Sebacic acid, supporting the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation. (PMID 3220884 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92057069f0>


  Mrv1652305261923582D          

 11 10  0  0  0  0            999 V2000
   -0.3265   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -0.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1049   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -0.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5324   -0.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    1.1276    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
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f92057069f0>

HMDB0000398
     RDKit          3D
3-Oxoadipic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.0018    1.1745   -0.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173    0.6084    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    1.3353    1.7096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409   -0.8291    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233   -1.0351   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -0.2893    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785    0.3865    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.3950   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    0.4048   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806   -0.0944    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    1.6888   -0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752    2.2488    1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9051   -1.2125    1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -1.3589    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -2.1307   -0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7944   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936   -1.4899   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -0.1623   -1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9563    1.9444   -0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007f92057069f0>


  Mrv1652305261923582D          

 11 10  0  0  0  0            999 V2000
   -0.3265   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -0.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1049   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -0.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5324   -0.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    1.1276    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
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047910

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
RTGHRDFWYQHVFW-UHFFFAOYSA-N

> <FORMULA>
C6H8O5

> <MOLECULAR_WEIGHT>
160.1247

> <EXACT_MASS>
160.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.910695418944067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxohexanedioic acid

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-0.1766289986666666

> <ALOGPS_LOGS>
-0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.235829200342627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4748505038613793

> <JCHEM_PKA_STRONGEST_BASIC>
-7.5471659957939785

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
33.4322

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxoadipic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f92057069f0>

HMDB0000398
     RDKit          3D
3-Oxoadipic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.0018    1.1745   -0.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173    0.6084    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    1.3353    1.7096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409   -0.8291    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233   -1.0351   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -0.2893    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785    0.3865    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.3950   -0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    0.4048   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806   -0.0944    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    1.6888   -0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752    2.2488    1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9051   -1.2125    1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -1.3589    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -2.1307   -0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7944   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936   -1.4899   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -0.1623   -1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9563    1.9444   -0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  8 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007f92057069f0>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.609  -0.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.730   0.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.942   0.560   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.609  -1.751   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.062  -0.212   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.274  -0.212   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.395   0.560   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.607   0.567   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.274  -1.751   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.727  -0.212   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.395   2.105   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8    9                                                  
CONECT    7    5   10   11                                                  
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f92057069f0>

COMPND    HMDB0000398
HETATM    1  O1  UNL     1      -3.002   1.174  -0.392  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.417   0.608   0.573  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.114   1.335   1.710  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.041  -0.829   0.523  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.823  -1.035  -0.361  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.347  -0.289   0.120  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.279   0.386   1.122  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.612  -0.395  -0.667  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.700   0.405  -0.064  1.00  0.00           C  
HETATM   10  O4  UNL     1       3.381  -0.094   0.863  1.00  0.00           O  
HETATM   11  O5  UNL     1       2.976   1.689  -0.503  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.675   2.249   1.676  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.905  -1.212   1.546  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.914  -1.359   0.079  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.594  -2.131  -0.335  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.104  -0.794  -1.386  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.894  -1.490  -0.608  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.446  -0.162  -1.742  1.00  0.00           H  
HETATM   19  H8  UNL     1       3.956   1.944  -0.611  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7    7    8
CONECT    8    9   17   18
CONECT    9   10   10   11
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007f92057069f0>

OC(=O)CCC(=O)CC(O)=O
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INCHI for #<Metabolite:0x00007f92057069f0>

InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)
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Synonyms
ValueSource
3-Keto-adipateChEBI
beta-Ketoadipic acidChEBI
beta-Oxoadipic acidChEBI
3-Keto-adipic acidGenerator
b-KetoadipateGenerator
b-Ketoadipic acidGenerator
beta-KetoadipateGenerator
Β-ketoadipateGenerator
Β-ketoadipic acidGenerator
b-OxoadipateGenerator
b-Oxoadipic acidGenerator
beta-OxoadipateGenerator
Β-oxoadipateGenerator
Β-oxoadipic acidGenerator
3-OxoadipateGenerator
3-KetoadipicHMDB
3-Oxoadipic acid, disodium saltHMDB
3-KetoadipateHMDB
3-Ketoadipic acidHMDB
3-OxohexanedioateHMDB
3-Oxohexanedioic acidHMDB
3-oxo-AdipateHMDB
3-Oxoadipic acidKEGG
Molecular FormulaC6H8O5
Average Mass160.1247
Monoisotopic Mass160.037173366
IUPAC Name3-oxohexanedioic acid
Traditional Name3-oxoadipic acid
CAS Registry Number689-31-6
SMILES
OC(=O)CCC(=O)CC(O)=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyRTGHRDFWYQHVFW-UHFFFAOYSA-N