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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 05:55:43 UTC

Update Date

2021-09-24 05:55:44 UTC

HMDB ID

HMDB0303951

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate

Description

(1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate, also known as shchc, belongs to gamma-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate can be found in a number of food items such as kiwi, muskmelon, purple laver, and lima bean, which makes (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate a potential biomarker for the consumption of these food products (1r,6r)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate may be a unique E.coli metabolite.

Structure

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

HMDB0303951
     RDKit          3D
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.8376   -0.2678   -1.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1202   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746    0.3489    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    0.3381   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.8103    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528    0.9874    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158    2.0468   -0.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.0089    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -1.1108    0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1106   -2.0975    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503   -1.8374    0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444   -0.6324    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8283    0.0109    1.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.3407   -0.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8254    0.5446   -1.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    0.4020   -2.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    0.8897   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.2991    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262   -0.6284   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849    1.0338   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    0.1754    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190    1.8080    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.3031    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143   -3.0197    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0897   -2.5934    1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800   -0.9263   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495    0.9655    1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    1.3538    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9179    0.9325   -1.6798 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14  8  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  6
 13 27  1  0
 14 28  1  1
 17 29  1  0
M  END

164
  Mrv0541 02241213022D          

 19 19  0  0  0  0            999 V2000
   -2.4034    0.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9744    1.2358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2600    1.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    0.5122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.1344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 18  1  6  0  0  0
  5  6  1  0  0  0  0
  5  9  1  6  0  0  0
  5 19  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303951

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(O)C=CC=C(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/t8-,10-/m1/s1

> <INCHI_KEY>
QJYRAJSESKVEAE-PSASIEDQSA-N

> <FORMULA>
C11H12O6

> <MOLECULAR_WEIGHT>
240.2094

> <EXACT_MASS>
240.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.355227336877054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.3190482766666666

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.340411281613098

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6252125068265864

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1354871525896746

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
57.88420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
shchc

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303951
     RDKit          3D
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.8376   -0.2678   -1.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1202   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746    0.3489    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    0.3381   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.8103    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528    0.9874    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158    2.0468   -0.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.0089    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -1.1108    0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1106   -2.0975    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503   -1.8374    0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444   -0.6324    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8283    0.0109    1.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.3407   -0.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8254    0.5446   -1.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    0.4020   -2.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    0.8897   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.2991    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262   -0.6284   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849    1.0338   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    0.1754    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190    1.8080    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.3031    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143   -3.0197    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0897   -2.5934    1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800   -0.9263   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495    0.9655    1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    1.3538    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9179    0.9325   -1.6798 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14  8  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  6
 13 27  1  0
 14 28  1  1
 17 29  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 164                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -4.486   0.767   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.153  -0.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.153  -1.543   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.819   0.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.819   2.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.485   3.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.848   2.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.848   0.767   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.153   3.077   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.485  -0.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.485  -1.543   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.819  -2.313   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.848  -2.313   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.182  -1.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.516  -2.313   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.849  -1.543   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.516  -3.853   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      -2.892   0.956   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.892   2.118   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10   18                                             
CONECT    5    4    6    9   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9    5                                                            
CONECT   10    4    8   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0303951
HETATM    1  O1  UNL     1       4.838  -0.268  -1.748  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.183   0.120  -0.766  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.775   0.349   0.470  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.744   0.338  -0.934  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.066   0.810   0.359  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.653   0.987   0.037  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.316   2.047  -0.547  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.410   0.009   0.348  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.092  -1.111   0.963  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.111  -2.097   1.289  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.350  -1.837   0.956  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.844  -0.632   0.274  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.828   0.011   1.047  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.783   0.341  -0.079  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.825   0.545  -1.575  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.809   0.402  -2.247  1.00  0.00           O  
HETATM   17  O6  UNL     1      -3.034   0.890  -2.130  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.978   1.299   0.795  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.226  -0.628  -1.175  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.485   1.034  -1.737  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.286   0.175   1.211  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.519   1.808   0.568  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.949  -1.303   1.230  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.814  -3.020   1.797  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.090  -2.593   1.212  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.380  -0.926  -0.688  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.650   0.966   1.010  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.077   1.354   0.319  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.918   0.932  -1.680  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7    8
CONECT    8    9    9   14
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   14   26
CONECT   13   27
CONECT   14   15   28
CONECT   15   16   16   17
CONECT   17   29
END

HMDB0303951
     RDKit          3D
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.8376   -0.2678   -1.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1202   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746    0.3489    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    0.3381   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.8103    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528    0.9874    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158    2.0468   -0.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.0089    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0921   -1.1108    0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1106   -2.0975    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503   -1.8374    0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444   -0.6324    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8283    0.0109    1.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.3407   -0.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8254    0.5446   -1.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    0.4020   -2.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0343    0.8897   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.2991    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262   -0.6284   -1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849    1.0338   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    0.1754    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190    1.8080    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.3031    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143   -3.0197    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0897   -2.5934    1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800   -0.9263   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495    0.9655    1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    1.3538    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9179    0.9325   -1.6798 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14  8  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  6
 13 27  1  0
 14 28  1  1
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate	ChEBI
(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate	ChEBI
SHCHC	ChEBI
(1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid	Generator
(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylic acid	Generator
2-(3-CARBOXYPROPIONYL)-6-hydroxy-cyclohexa-2,4-diene carboxylate	Generator
2-(3-CARBOXYPROPIONYL)-6-hydroxy-cyclohexa-2,4-diene carboxylIC ACID	ChEBI
2-Succinyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid	MeSH

Chemical Formula

C₁₁H₁₂O₆

Average Molecular Weight

240.2094

Monoisotopic Molecular Weight

240.063388116

IUPAC Name

(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

Traditional Name

shchc

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)C=CC=C(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

InChI Identifier

InChI=1S/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/t8-,10-/m1/s1

InChI Key

QJYRAJSESKVEAE-PSASIEDQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Beta-hydroxy acid
Short-chain keto acid
Dicarboxylic acid or derivatives
Hydroxy acid
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

2-succinyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid (CHEBI:39564 )

Ontology

Not Available

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Fox grape (FooDB: FOOD00228)
Summer grape (FooDB: FOOD00227)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Menaquinol Biosythesis (PathBank: SMP0001911)

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	-0.41	ALOGPS
logP	-0.32	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.88 m³·mol⁻¹	ChemAxon
Polarizability	22.36 Å³	ChemAxon
Number of Rings	1	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
AllCCS	[M+H]+	153.261	32859911
AllCCS	[M+H-H2O]+	149.588	32859911
AllCCS	[M+Na]+	157.654	32859911
AllCCS	[M+NH4]+	156.672	32859911
AllCCS	[M-H]-	150.802	32859911
AllCCS	[M+Na-2H]-	150.998	32859911
AllCCS	[M+HCOO]-	151.317	32859911
DeepCCS	[M+H]+	152.704	30932474
DeepCCS	[M-H]-	149.919	30932474
DeepCCS	[M-2H]-	185.182	30932474
DeepCCS	[M+Na]+	161.472	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C	2309.7	Semi standard non polar	33892256
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C	2227.2	Standard non polar	33892256
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C	2513.9	Standard polar	33892256
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C(C)(C)C	3223.6	Semi standard non polar	33892256
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C(C)(C)C	2899.7	Standard non polar	33892256
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)O[Si](C)(C)C(C)(C)C	2852.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 10V, Positive-QTOF	splash10-05fr-0490000000-37505c4f192c710ecbdd	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 20V, Positive-QTOF	splash10-05dj-1930000000-0ccde18fc3075d5de1db	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 40V, Positive-QTOF	splash10-0fba-6900000000-bb7e8d68ddedc2ae3c32	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 10V, Negative-QTOF	splash10-007a-0790000000-0c85a3ccb30906916a7f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 20V, Negative-QTOF	splash10-004j-1920000000-ecbb05382b6022769f05	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 40V, Negative-QTOF	splash10-054w-5900000000-64762261e0a1410c1df8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 10V, Positive-QTOF	splash10-0095-0980000000-b49a6f77798946f0b1ba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 20V, Positive-QTOF	splash10-0kor-2940000000-3a30aea0722211361a06	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 40V, Positive-QTOF	splash10-0ukj-9700000000-4e419d6f1a3b4d06cde0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 10V, Negative-QTOF	splash10-00g0-0790000000-336b6842611dcb1f850b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 20V, Negative-QTOF	splash10-00di-3900000000-92eba81c88d70bc51a87	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate 40V, Negative-QTOF	splash10-00dl-5900000000-d2ff63b73db8fd6374c1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06864

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030089

KNApSAcK ID

Not Available

Chemspider ID

4449817

KEGG Compound ID

C05817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

39564

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

Not Available

Showing metabocard for (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate (HMDB0303951)

MOL for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D MOL for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D SDF for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D-SDF for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

PDB for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D PDB for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

SMILES for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

INCHI for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

Structure for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D Structure for HMDB0303951 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra