Showing metabocard for (4S)-4,6-Dihydroxy-2,5-dioxohexanoate (MMDBc0029951)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:48:04 UTC
Update Date2022-08-31 17:37:55 UTC
Metabolite IDMMDBc0029951
Metabolite Identification
Common Name(4S)-4,6-Dihydroxy-2,5-dioxohexanoate
Description(4S)-4,6-Dihydroxy-2,5-dioxohexanoate (2,5-Diketo-3-deoxy-D-gluconate or 3-Deoxy-D-glycero-2,5-hexodiulosonate) is involved in pentose and glucuronate interconversions. It is a substrate for 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase. This enzyme catalyzes the reduction of 2,5-diketo-3-deoxygluconate (DKII or 4,6-dihydroxy-2,5-dioxohexanoate) into 2-keto-3-deoxygluconate (KDG or 2-dehydro-3-deoxygluconate) with a concomitant oxidation of NADH. It is also a substrate for 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase. This enzyme catalyzes the isomerization of 5-dehydro-4-deoxy-D-glucuronate to 3-deoxy-D-glycero-2,5-hexodiulosonate.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f91f9f7d5e0>


  Mrv0541 08131209212D          

 13 12  0  0  0  0            999 V2000
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  3  8  1  6  0  0  0
  9  4  2  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  6  2  0  0  0  0
  3 13  1  6  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f91f9f7d5e0>

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3D SDF for #<Metabolite:0x00007f91f9f7d5e0>

  Mrv0541 08131209212D          

 13 12  0  0  0  0            999 V2000
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  3  8  1  6  0  0  0
  9  4  2  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  6  2  0  0  0  0
  3 13  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029951

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(CC(=O)C(O)=O)C(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1

> <INCHI_KEY>
IBGYNIRCYXIAON-VKHMYHEASA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
14.892753513725122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4,6-dihydroxy-2,5-dioxohexanoic acid

> <ALOGPS_LOGP>
-1.35

> <JCHEM_LOGP>
-1.3120442836666666

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.99776118841174

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.739548997949559

> <JCHEM_PKA_STRONGEST_BASIC>
-3.326032682798515

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
35.4745

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-diketo-3-deoxy-D-gluconate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f91f9f7d5e0>
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PDB for #<Metabolite:0x00007f91f9f7d5e0>
HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    5    7                                                       
CONECT    3    1    5    8   13                                             
CONECT    4    1    6    9                                                  
CONECT    5    2    3   10                                                  
CONECT    6    4   11   12                                                  
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for #<Metabolite:0x00007f91f9f7d5e0>
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SMILES for #<Metabolite:0x00007f91f9f7d5e0>
[H][C@](O)(CC(=O)C(O)=O)C(=O)CO
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INCHI for #<Metabolite:0x00007f91f9f7d5e0>
InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1
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Synonyms
ValueSource
2,5-Diketo-3-deoxy-D-gluconateChEBI
3-Deoxy-D-glycero-2,5-hexodiulosonateChEBI
2,5-Diketo-3-deoxy-D-gluconic acidGenerator
3-Deoxy-D-glycero-2,5-hexodiulosonic acidGenerator
(4S)-4,6-Dihydroxy-2,5-dioxohexanoic acidGenerator
3-Deoxy-D-glycero-hexo-2,5-diulosonateGenerator
Molecular FormulaC6H8O6
Average Mass176.1241
Monoisotopic Mass176.032087988
IUPAC Name(4S)-4,6-dihydroxy-2,5-dioxohexanoic acid
Traditional Name2,5-diketo-3-deoxy-D-gluconate
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CC(=O)C(O)=O)C(=O)CO
InChI Identifier
InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1
InChI KeyIBGYNIRCYXIAON-VKHMYHEASA-N