Hmdb loader

Showing metabocard for Enol-phenylpyruvate (HMDB0012225)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:21:19 UTC
Update Date2023-02-21 17:17:44 UTC
HMDB IDHMDB0012225
Secondary Accession Numbers
  • HMDB12225
Metabolite Identification
Common NameEnol-phenylpyruvate
DescriptionEnol-phenylpyruvate belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Enol-phenylpyruvate has been detected, but not quantified in, several different foods, such as greenthread teas (Thelesperma), squashberries (Viburnum edule), chives (Allium schoenoprasum), german camomiles (Matricaria recutita), and rowals (Pangium edule). This could make enol-phenylpyruvate a potential biomarker for the consumption of these foods. Enol-phenylpyruvate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Enol-phenylpyruvate.
Structure
Data?1676999864
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012225 (Enol-phenylpyruvate)


  Mrv0541 02241203512D          

 12 12  0  0  0  0            999 V2000
    4.8126   -2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981   -2.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5270   -2.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8122   -3.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -3.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -3.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -4.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120   -4.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120   -5.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -6.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -5.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832   -4.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0012225 (Enol-phenylpyruvate)

HMDB0012225
     RDKit          3D
Enol-phenylpyruvate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7594   -0.1276   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1703    0.5829    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    1.4371    1.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.5276    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    1.3166    1.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -0.2800   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108   -0.3447   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    0.7211   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6336    0.5612    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1919   -0.6911    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296   -1.7826    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -1.6098   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    1.1970    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790    2.3157    1.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082   -0.9229   -1.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    1.7102   -0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.4362    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2589   -0.7810    0.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673   -2.7560    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -2.5099   -0.1106 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
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0012225 (Enol-phenylpyruvate)


  Mrv0541 02241203512D          

 12 12  0  0  0  0            999 V2000
    4.8126   -2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981   -2.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5270   -2.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8122   -3.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -3.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -3.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -4.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120   -4.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120   -5.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -6.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -5.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832   -4.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012225

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(\O)=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)/b8-6-

> <INCHI_KEY>
DEDGUGJNLNLJSR-VURMDHGXSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.215671259579608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-hydroxy-3-phenylprop-2-enoic acid

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.6174285786666662

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.747023229511157

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5885332172336084

> <JCHEM_PKA_STRONGEST_BASIC>
-6.087588205395375

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.02730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DL-α-hydroxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012225 (Enol-phenylpyruvate)

HMDB0012225
     RDKit          3D
Enol-phenylpyruvate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7594   -0.1276   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1703    0.5829    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    1.4371    1.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.5276    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    1.3166    1.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -0.2800   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108   -0.3447   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    0.7211   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6336    0.5612    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1919   -0.6911    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296   -1.7826    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -1.6098   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    1.1970    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790    2.3157    1.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5082   -0.9229   -1.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    1.7102   -0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.4362    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2589   -0.7810    0.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673   -2.7560    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -2.5099   -0.1106 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
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for HMDB0012225 (Enol-phenylpyruvate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.984  -4.632   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.650  -3.862   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.317  -3.862   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.983  -6.171   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.317  -6.941   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.649  -6.941   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.649  -8.481   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.982  -9.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.982 -10.791   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.649 -11.561   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.315 -10.791   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.315  -9.251   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for HMDB0012225 (Enol-phenylpyruvate)

COMPND    HMDB0012225
HETATM    1  O1  UNL     1       3.759  -0.128  -0.561  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.170   0.583   0.279  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.925   1.437   1.063  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.721   0.528   0.444  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.079   1.317   1.378  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.027  -0.280  -0.304  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.411  -0.345  -0.135  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.261   0.721  -0.041  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.634   0.561   0.139  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.192  -0.691   0.232  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.330  -1.783   0.136  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.975  -1.610  -0.045  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.841   1.197   1.430  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.279   2.316   1.370  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.508  -0.923  -1.064  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.835   1.710  -0.113  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.289   1.436   0.220  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.259  -0.781   0.379  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.767  -2.756   0.209  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.358  -2.510  -0.111  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    6    6
CONECT    5   14
CONECT    6    7   15
CONECT    7    8    8   12
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11   18
CONECT   11   12   12   19
CONECT   12   20
END
Download

SMILES for HMDB0012225 (Enol-phenylpyruvate)

OC(=O)C(\O)=C\C1=CC=CC=C1
Download

INCHI for HMDB0012225 (Enol-phenylpyruvate)

InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)/b8-6-
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
enol-Phenylpyruvic acidKegg
enol-alpha-Ketohydrocinnamic acidKegg
enol-a-KetohydrocinnamateGenerator
enol-a-Ketohydrocinnamic acidGenerator
enol-alpha-KetohydrocinnamateGenerator
enol-Α-ketohydrocinnamateGenerator
enol-Α-ketohydrocinnamic acidGenerator
2-Hydroxy-3-phenylpropenoateHMDB
2-Hydroxy-3-phenylpropenoic acidHMDB, Generator
PhenylpyruvateHMDB
enol-PhenylpyruvateKEGG
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2Z)-2-hydroxy-3-phenylprop-2-enoic acid
Traditional NameDL-α-hydroxycinnamic acid
CAS Registry Number5801-57-0
SMILES
OC(=O)C(\O)=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)/b8-6-
InChI KeyDEDGUGJNLNLJSR-VURMDHGXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Enol-phenylpyruvate
  • Cinnamic acid or derivatives
  • Cinnamic acid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
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 Solubility1.05 g/LALOGPS
logP1.55ALOGPS
logP1.62ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.03 m³·mol⁻¹ChemAxon
Polarizability16.22 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]+135.19430932474
DeepCCS[M-H]-132.65230932474
DeepCCS[M-2H]-168.29830932474
DeepCCS[M+Na]+143.37530932474
AllCCS[M+H]+134.732859911
AllCCS[M+H-H2O]+130.232859911
AllCCS[M+NH4]+138.832859911
AllCCS[M+Na]+140.032859911
AllCCS[M-H]-131.932859911
AllCCS[M+Na-2H]-132.832859911
AllCCS[M+HCOO]-133.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.31 minutes32390414
Predicted by Siyang on May 30, 202211.8516 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.87 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1775.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid391.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid131.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid236.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid162.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid532.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid455.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)129.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid948.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid355.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1132.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid301.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid405.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate516.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA263.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water135.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Enol-phenylpyruvateOC(=O)C(\O)=C\C1=CC=CC=C12678.6Standard polar33892256
Enol-phenylpyruvateOC(=O)C(\O)=C\C1=CC=CC=C11477.9Standard non polar33892256
Enol-phenylpyruvateOC(=O)C(\O)=C\C1=CC=CC=C11535.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enol-phenylpyruvate,1TMS,isomer #1C[Si](C)(C)OC(=O)/C(O)=C/C1=CC=CC=C11654.8Semi standard non polar33892256
Enol-phenylpyruvate,1TMS,isomer #2C[Si](C)(C)O/C(=C\C1=CC=CC=C1)C(=O)O1669.7Semi standard non polar33892256
Enol-phenylpyruvate,2TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C/C1=CC=CC=C1)O[Si](C)(C)C1615.5Semi standard non polar33892256
Enol-phenylpyruvate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(O)=C/C1=CC=CC=C11893.6Semi standard non polar33892256
Enol-phenylpyruvate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O/C(=C\C1=CC=CC=C1)C(=O)O1924.3Semi standard non polar33892256
Enol-phenylpyruvate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2099.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enol-phenylpyruvate GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-5900000000-07a9ccc24b7ad66a59682017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enol-phenylpyruvate GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9670000000-d024b973929302194fed2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enol-phenylpyruvate 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 - Enol-phenylpyruvate 10V, Positive-QTOFsplash10-014j-1900000000-f12b39c1d374881c9d922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 20V, Positive-QTOFsplash10-014m-3900000000-a34acb2eaa08f8dd34f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 40V, Positive-QTOFsplash10-0006-9300000000-0a8c8446d21d68f2bc422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 10V, Negative-QTOFsplash10-03di-0900000000-b2326bee6ab6a67c10db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 20V, Negative-QTOFsplash10-02tc-4900000000-6653ccc39bf1df275eb02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 40V, Negative-QTOFsplash10-014l-8900000000-8729ced74e114658afa62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 10V, Negative-QTOFsplash10-03xr-0900000000-984ecdf21cdafac77fb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 20V, Negative-QTOFsplash10-00kf-9800000000-11fdfc299dc6de7cf6982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 40V, Negative-QTOFsplash10-0006-9300000000-6e597f6e10d803f677902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 10V, Positive-QTOFsplash10-014l-5900000000-986457b755b06e8364752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 20V, Positive-QTOFsplash10-0006-9500000000-16341ab51a4f4937a3352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enol-phenylpyruvate 40V, Positive-QTOFsplash10-0006-9100000000-6c4342e7a7da48b645f72021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028869
KNApSAcK IDNot Available
Chemspider ID556910
KEGG Compound IDC02763
BioCyc IDENOL-PHENYLPYRUVATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound641637
PDB IDNot Available
ChEBI ID16815
Food Biomarker OntologyNot Available
VMH IDM00647
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Macrophage migration inhibitory factor
General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
Phenylpyruvic acid → Enol-phenylpyruvatedetails
Phenylpyruvic acid → Enol-phenylpyruvatedetails
References
  1. KNOX WE, PITT BM: Enzymic catalysis of the keto-enol tautomerization of phenylpyruvic acids. J Biol Chem. 1957 Apr;225(2):675-88. [PubMed:13416270 ]