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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 07:03:31 UTC

Update Date

2021-09-24 07:03:32 UTC

HMDB ID

HMDB0304086

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate

Description

2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate can be found in a number of food items such as feijoa, german camomile, sugar apple, and rapini, which makes 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304086
     RDKit          3D
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.7075    0.3621   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    1.1403   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988    0.6387    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181    0.1807    0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.1830   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609    0.5765   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025   -0.6995   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047   -1.1016   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -2.2886    0.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914   -0.1138   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    0.4995    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.4637    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7329    2.4088   -0.4000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    1.3542    0.8329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1193   -1.7076    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724   -3.0350   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -3.3861   -1.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -3.9766    0.4092 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4590   -1.1020   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735   -2.0224   -0.0682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    2.5784   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    3.0298   -1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    3.4062    0.3329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7338   -0.7358   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4615    0.8149   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.0063    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    1.4223   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.1507    0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4798    1.2868   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242    0.5848   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.7417   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    0.9966    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256   -0.3063    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7211    1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -0.9011   -1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -2.2325    0.8904 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 19  4  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
M  CHG  3  14  -1  18  -1  23  -1
M  END

  Mrv0541 01211515252D          

 23 23  0  0  0  0            999 V2000
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  2  0  0  0  0
  7  2  2  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  6  1  0  0  0  0
 23  9  1  0  0  0  0
M  CHG  3  17  -1  20  -1  22  -1
M  END
> <DATABASE_ID>
HMDB0304086

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(CC=C(C1C([O-])=O)C(=O)CCC([O-])=O)OC(=C)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,9,11-12,18H,1,3-5H2,(H,16,17)(H,19,20)(H,21,22)/p-3

> <INCHI_KEY>
JKJGLRGLOMRXFN-UHFFFAOYSA-K

> <FORMULA>
C14H13O9

> <MOLECULAR_WEIGHT>
325.251

> <EXACT_MASS>
325.057602738

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.70031820844286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1-carboxylatoeth-1-en-1-yl)oxy]-2-(3-carboxylatopropanoyl)-6-hydroxycyclohex-2-ene-1-carboxylate

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
-0.5422436176666664

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.742172788572854

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.175921347115915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4187637794557153

> <JCHEM_POLAR_SURFACE_AREA>
166.92

> <JCHEM_REFRACTIVITY>
106.54310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1-carboxylatoeth-1-en-1-yl)oxy]-2-(3-carboxylatopropanoyl)-6-hydroxycyclohex-2-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304086
     RDKit          3D
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.7075    0.3621   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    1.1403   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988    0.6387    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181    0.1807    0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.1830   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609    0.5765   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025   -0.6995   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047   -1.1016   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -2.2886    0.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914   -0.1138   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    0.4995    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.4637    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7329    2.4088   -0.4000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    1.3542    0.8329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1193   -1.7076    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724   -3.0350   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -3.3861   -1.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -3.9766    0.4092 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4590   -1.1020   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735   -2.0224   -0.0682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    2.5784   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    3.0298   -1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    3.4062    0.3329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7338   -0.7358   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4615    0.8149   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.0063    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    1.4223   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.1507    0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4798    1.2868   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242    0.5848   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.7417   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    0.9966    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256   -0.3063    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7211    1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -0.9011   -1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -2.2325    0.8904 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 19  4  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
M  CHG  3  14  -1  18  -1  23  -1
M  END

HEADER    PROTEIN                                 21-JAN-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-15         0                                  
HETATM    1  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    4    7                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    1   13   23                                                  
CONECT    7    2    8   11                                                  
CONECT    8    3    7   15                                                  
CONECT    9    4   12   23                                                  
CONECT   10    5   16   17                                                  
CONECT   11    7   12   14                                                  
CONECT   12    9   11   18                                                  
CONECT   13    6   19   20                                                  
CONECT   14   11   21   22                                                  
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0304086
HETATM    1  C1  UNL     1      -4.708   0.362  -0.717  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.850   1.140  -0.103  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.899   0.639   0.708  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.618   0.181   0.497  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.681   1.183  -0.112  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.661   0.577  -0.189  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.902  -0.700  -0.015  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.305  -1.102  -0.134  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.625  -2.289   0.022  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.391  -0.114  -0.442  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.985   0.499   0.783  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.018   1.464   0.376  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.733   2.409  -0.400  1.00  0.00           O  
HETATM   14  O4  UNL     1       6.332   1.354   0.833  1.00  0.00           O1-
HETATM   15  C11 UNL     1      -0.119  -1.708   0.287  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.072  -3.035  -0.273  1.00  0.00           C  
HETATM   17  O5  UNL     1      -0.418  -3.386  -1.355  1.00  0.00           O  
HETATM   18  O6  UNL     1       0.828  -3.977   0.409  1.00  0.00           O1-
HETATM   19  C13 UNL     1      -1.459  -1.102  -0.258  1.00  0.00           C  
HETATM   20  O7  UNL     1      -2.473  -2.022  -0.068  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.950   2.578  -0.319  1.00  0.00           C  
HETATM   22  O8  UNL     1      -4.848   3.030  -1.096  1.00  0.00           O  
HETATM   23  O9  UNL     1      -3.061   3.406   0.333  1.00  0.00           O1-
HETATM   24  H1  UNL     1      -4.734  -0.736  -0.631  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.462   0.815  -1.363  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.193  -0.006   1.546  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.976   1.422  -1.173  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.672   2.151   0.435  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.480   1.287  -0.405  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.124   0.585  -1.231  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.235  -0.742  -0.890  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.203   0.997   1.404  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.426  -0.306   1.402  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.333  -1.721   1.396  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.334  -0.901  -1.332  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.534  -2.233   0.890  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   21
CONECT    3    4
CONECT    4    5   19   26
CONECT    5    6   27   28
CONECT    6    7    7   29
CONECT    7    8   15
CONECT    8    9    9   10
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   13   14
CONECT   15   16   19   34
CONECT   16   17   17   18
CONECT   19   20   35
CONECT   20   36
CONECT   21   22   22   23
END

HMDB0304086
     RDKit          3D
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.7075    0.3621   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    1.1403   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988    0.6387    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181    0.1807    0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    1.1830   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609    0.5765   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025   -0.6995   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047   -1.1016   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251   -2.2886    0.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914   -0.1138   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    0.4995    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.4637    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7329    2.4088   -0.4000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    1.3542    0.8329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1193   -1.7076    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724   -3.0350   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -3.3861   -1.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -3.9766    0.4092 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4590   -1.1020   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735   -2.0224   -0.0682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    2.5784   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    3.0298   -1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    3.4062    0.3329 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7338   -0.7358   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4615    0.8149   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.0063    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    1.4223   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.1507    0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4798    1.2868   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242    0.5848   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.7417   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    0.9966    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256   -0.3063    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7211    1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -0.9011   -1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -2.2325    0.8904 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 19  4  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
M  CHG  3  14  -1  18  -1  23  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-[(1-Carboxylatoeth-1-en-1-yl)oxy]-2-(3-carboxylatopropanoyl)-6-hydroxycyclohex-2-ene-1-carboxylic acid	Generator
2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid	Generator

Chemical Formula

C₁₄H₁₃O₉

Average Molecular Weight

325.251

Monoisotopic Molecular Weight

325.057602738

IUPAC Name

5-[(1-carboxylatoeth-1-en-1-yl)oxy]-2-(3-carboxylatopropanoyl)-6-hydroxycyclohex-2-ene-1-carboxylate

Traditional Name

5-[(1-carboxylatoeth-1-en-1-yl)oxy]-2-(3-carboxylatopropanoyl)-6-hydroxycyclohex-2-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

OC1C(CC=C(C1C([O-])=O)C(=O)CCC([O-])=O)OC(=C)C([O-])=O

InChI Identifier

InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,9,11-12,18H,1,3-5H2,(H,16,17)(H,19,20)(H,21,22)/p-3

InChI Key

JKJGLRGLOMRXFN-UHFFFAOYSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-9924 )

Ontology

Not Available

Exogenous (HMDB: HMDB0304086)

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)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
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)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

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)

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	0.44	ALOGPS
logP	-0.54	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	166.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.54 m³·mol⁻¹	ChemAxon
Polarizability	28.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	171.161	32859911
AllCCS	[M+H-H2O]+	168.109	32859911
AllCCS	[M+Na]+	174.793	32859911
AllCCS	[M+NH4]+	173.983	32859911
AllCCS	[M-H]-	166.335	32859911
AllCCS	[M+Na-2H]-	165.89	32859911
AllCCS	[M+HCOO]-	165.531	32859911
DeepCCS	[M+H]+	171.255	30932474
DeepCCS	[M-H]-	168.897	30932474
DeepCCS	[M-2H]-	202.049	30932474
DeepCCS	[M+Na]+	178.049	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C)C(=O)[O-]	2550.0	Semi standard non polar	33892256
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C)C(=O)[O-]	2357.8	Standard non polar	33892256
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C)C(=O)[O-]	3206.1	Standard polar	33892256
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TBDMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C(C)(C)C)C(=O)[O-]	2998.6	Semi standard non polar	33892256
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TBDMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C(C)(C)C)C(=O)[O-]	2793.4	Standard non polar	33892256
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate,2TBDMS,isomer #1	C=C(OC1CC=C(C(=CCC(=O)[O-])O[Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1O[Si](C)(C)C(C)(C)C)C(=O)[O-]	3341.5	Standard polar	33892256

Spectra

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030361

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

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

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

Not Available

Showing metabocard for 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (HMDB0304086)

MOL for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

3D MOL for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

3D SDF for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

3D-SDF for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

PDB for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

3D PDB for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

SMILES for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

INCHI for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

Structure for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

3D Structure for HMDB0304086 (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized