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Showing metabocard for Prephenate (HMDB0012283)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:18 UTC
Update Date2021-09-07 17:05:28 UTC
HMDB IDHMDB0012283
Secondary Accession Numbers
  • HMDB12283
Metabolite Identification
Common NamePrephenate
DescriptionPrephenate (CAS: 126-49-8), also known as prephenic acid, 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. Prephenic acid is an example of an achiral (optically inactive) molecule which has two pseudoasymmetric atoms (i.e. stereogenic but not chirotopic centers): the C1 and the C4 cyclohexadiene ring atoms. Prephenate exists in all living species, ranging from bacteria to humans. Prephenate has been detected, but not quantified, in several different foods, such as American pokeweeds, breadnut tree seeds, common wheats, swiss chards, and breadfruits. The other stereoisomer, i.e. trans or, better, (1r, 4r), is called epiprephenic acid. It has been shown that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s, 4s) according to the new IUPAC stereochemistry rules (2013). It is biosynthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate. Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.
Structure
Data?1583173770
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012283 (Prephenate)


  Mrv1652309042000352D          

 16 16  0  0  0  0            999 V2000
10000.733910000.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7339 9999.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4449 9998.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1601 9999.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4449 9998.1615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0188 9998.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.725710001.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.438810000.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.725710001.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8698 9999.3849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.298310001.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.583810000.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5838 9999.7972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2983 9999.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0128 9999.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.012810000.6223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16  1  1  6  0  0  0
 16  7  1  0  0  0  0
 13 10  1  1  0  0  0
M  END
Download

3D MOL for HMDB0012283 (Prephenate)

HMDB0012283
     RDKit          3D
Prephenate
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.3153    1.2772    1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248    1.2370    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631    1.8062   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0793    0.5598   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953    0.5242   -1.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -0.0728    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -0.7226   -0.0451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6346   -1.7582   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -2.0007   -0.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -2.4508   -1.8185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476    0.3413   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.9781   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305    0.6124    0.9506 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5994    0.9378    1.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759   -0.8338    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4590    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522    2.5043   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141    0.7561    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263   -0.8005    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777   -2.6141   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2642    0.5972   -1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186    1.7718   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    1.2133    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    1.4714    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370   -1.3631    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -2.5127    1.0010 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16  7  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  1
 14 24  1  0
 15 25  1  0
 16 26  1  0
M  END
Download

3D SDF for HMDB0012283 (Prephenate)


  Mrv1652309042000352D          

 16 16  0  0  0  0            999 V2000
10000.733910000.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7339 9999.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4449 9998.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1601 9999.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4449 9998.1615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0188 9998.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.725710001.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.438810000.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.725710001.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8698 9999.3849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.298310001.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.583810000.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5838 9999.7972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2983 9999.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0128 9999.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.012810000.6223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16  1  1  6  0  0  0
 16  7  1  0  0  0  0
 13 10  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0012283

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+

> <INCHI_KEY>
FPWMCUPFBRFMLH-XGAOUMNUSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.1828

> <EXACT_MASS>
226.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.731181576772162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
0.06097045266666673

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.87542455823727

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.891510507673819

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1244212194274477

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
53.55400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prephenic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012283 (Prephenate)

HMDB0012283
     RDKit          3D
Prephenate
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.3153    1.2772    1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248    1.2370    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631    1.8062   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0793    0.5598   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953    0.5242   -1.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -0.0728    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -0.7226   -0.0451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6346   -1.7582   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -2.0007   -0.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -2.4508   -1.8185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476    0.3413   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.9781   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305    0.6124    0.9506 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5994    0.9378    1.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759   -0.8338    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4590    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522    2.5043   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141    0.7561    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263   -0.8005    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777   -2.6141   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2642    0.5972   -1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186    1.7718   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    1.2133    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    1.4714    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370   -1.3631    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -2.5127    1.0010 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16  7  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  1
 14 24  1  0
 15 25  1  0
 16 26  1  0
M  END
Download

PDB for HMDB0012283 (Prephenate)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0378667.085   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.0378665.545   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.3648664.774   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6998665.545   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.3648663.235   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8666.7028664.774   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8668.0218668.597   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8669.3528667.827   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8668.0218670.136   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8662.6908665.518   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8665.3578668.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0238667.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0238666.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.3578665.518   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.6918666.288   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.6918667.828   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    8    9   16                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   13                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   10                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15    1    7                                             
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END
Download

3D PDB for HMDB0012283 (Prephenate)

COMPND    HMDB0012283
HETATM    1  O1  UNL     1       3.315   1.277   1.775  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.225   1.237   0.525  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.163   1.806  -0.309  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.079   0.560  -0.059  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.995   0.524  -1.308  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.037  -0.073   0.821  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.016  -0.723  -0.045  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.635  -1.758  -0.876  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.839  -2.001  -0.718  1.00  0.00           O  
HETATM   10  O5  UNL     1      -0.088  -2.451  -1.818  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.648   0.341  -0.847  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.702   0.978  -0.374  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.230   0.612   0.951  1.00  0.00           C  
HETATM   14  O6  UNL     1      -3.599   0.938   1.029  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.076  -0.834   1.252  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.019  -1.459   0.773  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.852   2.504  -0.965  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.614   0.756   1.414  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.526  -0.801   1.487  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.078  -2.614  -1.600  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.264   0.597  -1.802  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.219   1.772  -0.908  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.698   1.213   1.736  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.888   1.471   0.262  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.837  -1.363   1.865  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.918  -2.513   1.001  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5    6
CONECT    6    7   18   19
CONECT    7    8   11   16
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   21
CONECT   12   13   22
CONECT   13   14   15   23
CONECT   14   24
CONECT   15   16   16   25
CONECT   16   26
END
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SMILES for HMDB0012283 (Prephenate)

O[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O
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INCHI for HMDB0012283 (Prephenate)

InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidChEBI
cis-Prephenic acidChEBI
Prephenic acid, cisChEBI
Prephenic acidKegg
cis-1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
cis-PrephenateGenerator
Prephenate, cisGenerator
(1S,4S)-PrephenateHMDB
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acidHMDB
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidHMDB
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acidHMDB
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
PPAHMDB
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
PrephenateGenerator
Chemical FormulaC10H10O6
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
IUPAC Name(1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Traditional Nameprephenic acid
CAS Registry Number87664-40-2
SMILES
O[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O
InChI Identifier
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+
InChI KeyFPWMCUPFBRFMLH-XGAOUMNUSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility36 g/LALOGPS
logP-0.31ALOGPS
logP0.061ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.55 m³·mol⁻¹ChemAxon
Polarizability19.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.24130932474
DeepCCS[M-H]-145.84630932474
DeepCCS[M-2H]-179.09230932474
DeepCCS[M+Na]+154.15430932474
AllCCS[M+H]+149.232859911
AllCCS[M+H-H2O]+145.432859911
AllCCS[M+NH4]+152.732859911
AllCCS[M+Na]+153.832859911
AllCCS[M-H]-146.132859911
AllCCS[M+Na-2H]-146.332859911
AllCCS[M+HCOO]-146.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PrephenateO[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O3353.9Standard polar33892256
PrephenateO[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O1467.9Standard non polar33892256
PrephenateO[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O1892.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prephenate,1TMS,isomer #1C[Si](C)(C)O[C@H]1C=C[C@@](CC(=O)C(=O)O)(C(=O)O)C=C12056.8Semi standard non polar33892256
Prephenate,1TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O)C=C[C@@H](O)C=C12047.4Semi standard non polar33892256
Prephenate,1TMS,isomer #3C[Si](C)(C)OC(=O)[C@]1(CC(=O)C(=O)O)C=C[C@H](O)C=C12000.8Semi standard non polar33892256
Prephenate,1TMS,isomer #4C[Si](C)(C)OC(=C[C@]1(C(=O)O)C=C[C@@H](O)C=C1)C(=O)O2162.5Semi standard non polar33892256
Prephenate,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C)C=C12042.7Semi standard non polar33892256
Prephenate,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@]1(CC(=O)C(=O)O)C=C[C@H](O[Si](C)(C)C)C=C12013.1Semi standard non polar33892256
Prephenate,2TMS,isomer #3C[Si](C)(C)OC(=C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C)C=C1)C(=O)O2150.9Semi standard non polar33892256
Prephenate,2TMS,isomer #4C[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O)C=C12014.1Semi standard non polar33892256
Prephenate,2TMS,isomer #5C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O)C=C[C@@H](O)C=C1)O[Si](C)(C)C2122.3Semi standard non polar33892256
Prephenate,2TMS,isomer #6C[Si](C)(C)OC(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O)C=C1)C(=O)O2130.9Semi standard non polar33892256
Prephenate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O[Si](C)(C)C)C=C12074.0Semi standard non polar33892256
Prephenate,3TMS,isomer #2C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C)C=C1)O[Si](C)(C)C2101.3Semi standard non polar33892256
Prephenate,3TMS,isomer #3C[Si](C)(C)OC(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O[Si](C)(C)C)C=C1)C(=O)O2178.4Semi standard non polar33892256
Prephenate,3TMS,isomer #4C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O)C=C1)O[Si](C)(C)C2068.3Semi standard non polar33892256
Prephenate,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O[Si](C)(C)C)C=C1)O[Si](C)(C)C2100.8Semi standard non polar33892256
Prephenate,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O[Si](C)(C)C)C=C1)O[Si](C)(C)C2065.2Standard non polar33892256
Prephenate,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C)C=C[C@@H](O[Si](C)(C)C)C=C1)O[Si](C)(C)C2346.5Standard polar33892256
Prephenate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@](CC(=O)C(=O)O)(C(=O)O)C=C12310.9Semi standard non polar33892256
Prephenate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O)C=C[C@@H](O)C=C12300.0Semi standard non polar33892256
Prephenate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@]1(CC(=O)C(=O)O)C=C[C@H](O)C=C12276.0Semi standard non polar33892256
Prephenate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=C[C@]1(C(=O)O)C=C[C@@H](O)C=C1)C(=O)O2386.5Semi standard non polar33892256
Prephenate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C12554.2Semi standard non polar33892256
Prephenate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@]1(CC(=O)C(=O)O)C=C[C@H](O[Si](C)(C)C(C)(C)C)C=C12570.1Semi standard non polar33892256
Prephenate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O2632.1Semi standard non polar33892256
Prephenate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O)C=C12490.4Semi standard non polar33892256
Prephenate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O)C=C[C@@H](O)C=C1)O[Si](C)(C)C(C)(C)C2562.7Semi standard non polar33892256
Prephenate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O)C=C1)C(=O)O2602.2Semi standard non polar33892256
Prephenate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C12774.2Semi standard non polar33892256
Prephenate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2784.1Semi standard non polar33892256
Prephenate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O2868.0Semi standard non polar33892256
Prephenate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O)C=C1)O[Si](C)(C)C(C)(C)C2763.0Semi standard non polar33892256
Prephenate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3011.9Semi standard non polar33892256
Prephenate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2701.2Standard non polar33892256
Prephenate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=C[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@@H](O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2677.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Prephenate EI-B (Non-derivatized)splash10-014u-6920000000-ef53f0db72ce3c5aa0c42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prephenate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d85352017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prephenate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 10V, Positive-QTOFsplash10-0a7i-0950000000-783758ab15df97a404b42017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 20V, Positive-QTOFsplash10-0bu9-1910000000-9f4b0bd1d617cf85c5b72017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 40V, Positive-QTOFsplash10-0a4i-3900000000-00e996c97c569d0bb94b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 10V, Negative-QTOFsplash10-004i-1790000000-a8695b0e797b6ea4a6c72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 20V, Negative-QTOFsplash10-01sr-1920000000-f17d05344ee2d90f01c12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 40V, Negative-QTOFsplash10-000f-8900000000-b4238cbdb48e66836fb12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 10V, Positive-QTOFsplash10-0a70-1970000000-7605a9b397a2136475b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 20V, Positive-QTOFsplash10-07br-3900000000-1f4d611e994bbc1e075f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 40V, Positive-QTOFsplash10-0a4i-3900000000-97a22d2d646aceb138b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 10V, Negative-QTOFsplash10-004r-1960000000-3645029a13932992cfb02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 20V, Negative-QTOFsplash10-03dr-0900000000-317567c1da99c003ef6c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prephenate 40V, Negative-QTOFsplash10-0a4u-4900000000-e8395b1eca4b111c28ce2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08427
Phenol Explorer Compound IDNot Available
FooDB IDFDB028914
KNApSAcK IDC00019632
Chemspider ID16735981
KEGG Compound IDC00254
BioCyc IDPREPHENATE
BiGG IDNot Available
Wikipedia LinkPrephenic_acid
METLIN IDNot Available
PubChem Compound363602639
PDB IDNot Available
ChEBI ID84387
Food Biomarker OntologyNot Available
VMH IDPPHN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. METZENBERG RL, MITCHELL HK: Isolation of prephenic acid from Neurospora. Arch Biochem Biophys. 1956 Sep;64(1):51-6. [PubMed:13363412 ]
  2. GAMBORG OL, SIMPSON FJ: PREPARATION OF PREPHENIC ACID AND ITS CONVERSION TO PHENYLALANINE AND TYROSINE BY PLANT ENZYMES. Can J Biochem. 1964 May;42:583-91. [PubMed:14185725 ]