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Showing metabocard for Phosphoenolpyruvic acid (HMDB0000263)

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enzymes (11)transporters (1) Show 12 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:40 UTC
HMDB IDHMDB0000263
Secondary Accession Numbers
  • HMDB00263
Metabolite Identification
Common NamePhosphoenolpyruvic acid
DescriptionPhosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia).
Structure
Data?1676999680
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000263 (Phosphoenolpyruvic acid)


  Mrv1652309152017202D          

 10  9  0  0  0  0            999 V2000
10014.207710014.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.923910014.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10013.492110014.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.207710013.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.638310014.3706    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10012.778410014.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10013.492110015.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.224710013.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.354710014.7845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.049710013.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
M  END
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3D MOL for HMDB0000263 (Phosphoenolpyruvic acid)

HMDB0000263
     RDKit          3D
Phosphoenolpyruvic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.5201    1.3322    1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.6067    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254    0.8887    0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -0.1003   -0.0983 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1377    0.3511    0.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0586   -1.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.6974    0.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.4585   -0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5239   -1.1606   -1.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.6858   -0.5431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    2.1100    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5841    1.1235    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    0.9549   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.6901    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9453   -1.6330   -0.6718 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  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  6 13  1  0
  7 14  1  0
 10 15  1  0
M  END
Download

3D SDF for HMDB0000263 (Phosphoenolpyruvic acid)


  Mrv1652309152017202D          

 10  9  0  0  0  0            999 V2000
10014.207710014.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.923910014.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10013.492110014.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.207710013.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.638310014.3706    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10012.778410014.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10013.492110015.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.224710013.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.354710014.7845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.049710013.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000263

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(=C)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)

> <INCHI_KEY>
DTBNBXWJWCWCIK-UHFFFAOYSA-N

> <FORMULA>
C3H5O6P

> <MOLECULAR_WEIGHT>
168.042

> <EXACT_MASS>
167.982374404

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.570833644416727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(phosphonooxy)prop-2-enoic acid

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-0.6395755343333333

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.5517999477775644

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.7594134980317975

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
30.131700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphoenolpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000263 (Phosphoenolpyruvic acid)

HMDB0000263
     RDKit          3D
Phosphoenolpyruvic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.5201    1.3322    1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.6067    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254    0.8887    0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -0.1003   -0.0983 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1377    0.3511    0.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0586   -1.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.6974    0.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.4585   -0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5239   -1.1606   -1.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.6858   -0.5431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    2.1100    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5841    1.1235    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    0.9549   -1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.6901    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9453   -1.6330   -0.6718 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  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  6 13  1  0
  7 14  1  0
 10 15  1  0
M  END
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PDB for HMDB0000263 (Phosphoenolpyruvic acid)

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  C   UNK     0    8693.1888693.492   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8694.5258694.261   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8691.8528694.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8693.1888691.952   0.000  0.00  0.00           C+0
HETATM    5  P   UNK     0    8695.8588693.492   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8690.5208693.492   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8691.8528695.801   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8695.0868692.160   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8697.1968694.264   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8696.6268692.160   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1                                                            
CONECT    5    2    8    9   10                                             
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0000263 (Phosphoenolpyruvic acid)

COMPND    HMDB0000263
HETATM    1  C1  UNL     1       1.520   1.332   1.052  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.712   0.607   0.314  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.625   0.889   0.375  1.00  0.00           O  
HETATM    4  P1  UNL     1      -1.898  -0.100  -0.098  1.00  0.00           P  
HETATM    5  O2  UNL     1      -3.138   0.351   0.676  1.00  0.00           O  
HETATM    6  O3  UNL     1      -2.146   0.059  -1.758  1.00  0.00           O  
HETATM    7  O4  UNL     1      -1.539  -1.697   0.331  1.00  0.00           O  
HETATM    8  C3  UNL     1       1.260  -0.459  -0.533  1.00  0.00           C  
HETATM    9  O5  UNL     1       0.524  -1.161  -1.241  1.00  0.00           O  
HETATM   10  O6  UNL     1       2.627  -0.686  -0.543  1.00  0.00           O  
HETATM   11  H1  UNL     1       1.104   2.110   1.669  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.584   1.124   1.017  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.581   0.955  -1.892  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.348  -1.690   1.302  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.945  -1.633  -0.672  1.00  0.00           H  
CONECT    1    2    2   11   12
CONECT    2    3    8
CONECT    3    4
CONECT    4    5    5    6    7
CONECT    6   13
CONECT    7   14
CONECT    8    9    9   10
CONECT   10   15
END
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SMILES for HMDB0000263 (Phosphoenolpyruvic acid)

OC(=O)C(=C)OP(O)(O)=O
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INCHI for HMDB0000263 (Phosphoenolpyruvic acid)

InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-(Phosphonooxy)-2-propenoic acidChEBI
2-PHOSPHOENOLPYRUVIC ACIDChEBI
PEPChEBI
PHOSPHOENOLPYRUVATEChEBI
2-(Phosphonooxy)-2-propenoateGenerator
2-PHOSPHOENOLPYRUVateGenerator
2-Hydroxy-acrylic acid dihydrogen phosphateHMDB
2-Phosphonooxyprop-2-enoateHMDB
2-Phosphonooxyprop-2-enoic acidHMDB
p-enol-PyruvateHMDB
PEP (phosphate)HMDB
Phosphoenolpyruvic acidHMDB
Chemical FormulaC3H5O6P
Average Molecular Weight168.042
Monoisotopic Molecular Weight167.982374404
IUPAC Name2-(phosphonooxy)prop-2-enoic acid
Traditional Namephosphoenolpyruvic acid
CAS Registry Number138-08-9
SMILES
OC(=O)C(=C)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChI KeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphate esters
Alternative Parents
Substituents
  • Phosphoric acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg122.330932474
[M-H]-Not Available164.278http://allccs.zhulab.cn/database/detail?ID=AllCCS00000084
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP-1.2ALOGPS
logP-0.64ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)0.76ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.13 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.12931661259
DarkChem[M-H]-128.30231661259
AllCCS[M+H]+137.70532859911
AllCCS[M-H]-126.77532859911
DeepCCS[M+H]+121.80530932474
DeepCCS[M-H]-118.22630932474
DeepCCS[M-2H]-155.54730932474
DeepCCS[M+Na]+130.58330932474
AllCCS[M+H]+137.732859911
AllCCS[M+H-H2O]+133.832859911
AllCCS[M+NH4]+141.432859911
AllCCS[M+Na]+142.432859911
AllCCS[M-H]-126.832859911
AllCCS[M+Na-2H]-129.032859911
AllCCS[M+HCOO]-131.532859911

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, 2022.2.2 minutes32390414
Predicted by Siyang on May 30, 20229.2317 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.81 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid425.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid501.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid356.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid52.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid244.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid89.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid298.1 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 Acid233.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)865.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid597.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid40.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid633.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid220.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid351.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate755.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA362.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water484.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phosphoenolpyruvic acidOC(=O)C(=C)OP(O)(O)=O2460.1Standard polar33892256
Phosphoenolpyruvic acidOC(=O)C(=C)OP(O)(O)=O1284.7Standard non polar33892256
Phosphoenolpyruvic acidOC(=O)C(=C)OP(O)(O)=O1402.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphoenolpyruvic acid,1TMS,isomer #1C=C(OP(=O)(O)O)C(=O)O[Si](C)(C)C1466.6Semi standard non polar33892256
Phosphoenolpyruvic acid,1TMS,isomer #2C=C(OP(=O)(O)O[Si](C)(C)C)C(=O)O1478.4Semi standard non polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1530.4Semi standard non polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1546.5Standard non polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1930.4Standard polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1564.6Semi standard non polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1542.3Standard non polar33892256
Phosphoenolpyruvic acid,2TMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1819.8Standard polar33892256
Phosphoenolpyruvic acid,3TMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1615.7Semi standard non polar33892256
Phosphoenolpyruvic acid,3TMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1606.9Standard non polar33892256
Phosphoenolpyruvic acid,3TMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1718.0Standard polar33892256
Phosphoenolpyruvic acid,1TBDMS,isomer #1C=C(OP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C1705.6Semi standard non polar33892256
Phosphoenolpyruvic acid,1TBDMS,isomer #2C=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O1732.5Semi standard non polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1966.1Semi standard non polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1933.9Standard non polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #1C=C(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2197.6Standard polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O1982.0Semi standard non polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O1950.9Standard non polar33892256
Phosphoenolpyruvic acid,2TBDMS,isomer #2C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2084.2Standard polar33892256
Phosphoenolpyruvic acid,3TBDMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2198.1Semi standard non polar33892256
Phosphoenolpyruvic acid,3TBDMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2144.2Standard non polar33892256
Phosphoenolpyruvic acid,3TBDMS,isomer #1C=C(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2102.7Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.6 +/- 2.9 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified17.4 +/- 3.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cellular CytoplasmDetected and Quantified17.0 (15.0-19.0) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified2.07 +/- 1.22 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.219 +/- 0.312 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.312 +/- 0.332 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.419 +/- 0.270 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.463 +/- 0.275 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.94 +/- 1.62 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified2.45 +/- 3.70 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified2.36 +/- 3.13 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDDB01819
Phenol Explorer Compound IDNot Available
FooDB IDFDB031112
KNApSAcK IDC00000798
Chemspider ID980
KEGG Compound IDC00074
BioCyc IDPHOSPHO-ENOL-PYRUVATE
BiGG IDNot Available
Wikipedia LinkPhosphoenolpyruvic_acid
METLIN IDNot Available
PubChem Compound1005
PDB IDNot Available
ChEBI ID44897
Food Biomarker OntologyNot Available
VMH IDPEP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSimon, Ethan S.; Grabowski, Sven; Whitesides, George M. Preparation of phosphoenolpyruvate from D-(-)-3-phosphoglyceric acid for use in regeneration of ATP. Journal of the American Chemical Society (1989), 111(24), 8920-1.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  3. Krogh P: Role of ochratoxin in disease causation. Food Chem Toxicol. 1992 Mar;30(3):213-24. [PubMed:1618445 ]
  4. Germaine GR, Tellefson LM: Promotion of Streptococcus mutans glucose transport by human whole saliva and parotid fluid. Infect Immun. 1985 Apr;48(1):7-13. [PubMed:3980096 ]
  5. Schatzberger P: Maternity services. BMJ. 1992 May 23;304(6838):1382-3. [PubMed:1611358 ]
  6. Orye E, Verhaaren H, Samuel K, van Mele B: A 46,XX,10Q+ chromosome constitution in a girl. Partial long arm duplication or insertional translocation? Humangenetik. 1975 May 26;28(1):1-8. [PubMed:1150258 ]
  7. Landau BR, Chandramouli V, Schumann WC, Ekberg K, Kumaran K, Kalhan SC, Wahren J: Estimates of Krebs cycle activity and contributions of gluconeogenesis to hepatic glucose production in fasting healthy subjects and IDDM patients. Diabetologia. 1995 Jul;38(7):831-8. [PubMed:7556986 ]
  8. Shirokane Y, Nakajima M, Mizusawa K: A new enzymatic assay of urinary guanidinoacetic acid. Clin Chim Acta. 1991 Oct 31;202(3):227-36. [PubMed:1667626 ]
  9. Tannen RL: Ammonia metabolism. Am J Physiol. 1978 Oct;235(4):F265-77. [PubMed:29492 ]
  10. Atkin BM, Buist NR, Utter MF, Leiter AB, Banker BQ: Pyruvate carboxylase deficiency and lactic acidosis in a retarded child without Leigh's disease. Pediatr Res. 1979 Feb;13(2):109-16. [PubMed:219411 ]
  11. Bojarska-Dahlig H, Gloabski T, Dzioegielewska I: [Salts of cyclic erythromycin A carbonate with cinnamic acid derivatives]. Acta Pol Pharm. 1975;32(3):311-7. [PubMed:1155186 ]
  12. Matsumoto T, van der Auwera P, Watanabe Y, Tanaka M, Ogata N, Naito S, Kumazawa J: Neutrophil function in hyperosmotic NaCl is preserved by phosphoenol pyruvate. Urol Res. 1991;19(4):223-7. [PubMed:1656579 ]
  13. Cahill GF Jr, Aoki TT: Renal gluconeogenesis and amino-acid metabolism in man. Med Clin North Am. 1975 May;59(3):751-61. [PubMed:1092934 ]
  14. Beyer C: Creatine measurement in serum and urine with an automated enzymatic method. Clin Chem. 1993 Aug;39(8):1613-9. [PubMed:8353946 ]
  15. Momeni N, Yoshimoto T, Ryberg B, Sandberg-Wollheim M, Grubb A: Factors influencing analysis of prolyl endopeptidase in human blood and cerebrospinal fluid: increase in assay sensitivity. Scand J Clin Lab Invest. 2003;63(6):387-95. [PubMed:14594319 ]
  16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Sialic acid synthase
General function:
Involved in catalytic activity
Specific function:
Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:
NANS
Uniprot ID:
Q9NR45
Molecular weight:
40307.26
Reactions
Phosphoenolpyruvic acid + N-Acetylmannosamine + Water → Phosphate + N-Acetylneuraminic aciddetails
Phosphoenolpyruvic acid + N-acyl-D-mannosamine 6-phosphate + Water → N-acylneuraminate 9-phosphate + Phosphatedetails
N-Acetylneuraminic acid 9-phosphate + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Phosphoenolpyruvic acid + Waterdetails
Enzyme Details
2. 6-phosphofructokinase type C
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKP
Uniprot ID:
Q01813
Molecular weight:
85595.405
Enzyme Details
3. 6-phosphofructokinase, liver type
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
Enzyme Details
4. 6-phosphofructokinase, muscle type
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKM
Uniprot ID:
P08237
Molecular weight:
85181.925
Enzyme Details
5. Pyruvate kinase isozymes M1/M2
General function:
Involved in magnesium ion binding
Specific function:
Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
Gene Name:
PKM
Uniprot ID:
P14618
Molecular weight:
65930.14
Reactions
Adenosine triphosphate + Pyruvic acid → ADP + Phosphoenolpyruvic aciddetails
Guanosine triphosphate + Pyruvic acid → Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Deoxyadenosine triphosphate + Pyruvic acid → dADP + Phosphoenolpyruvic aciddetails
dGTP + Pyruvic acid → dGDP + Phosphoenolpyruvic aciddetails
Nucleoside triphosphate + Pyruvic acid → NDP + Phosphoenolpyruvic aciddetails
ADP + Phosphoenolpyruvic acid → Adenosine triphosphate + Pyruvic aciddetails
Enzyme Details
6. Pyruvate kinase isozymes R/L
General function:
Involved in magnesium ion binding
Specific function:
Plays a key role in glycolysis (By similarity).
Gene Name:
PKLR
Uniprot ID:
P30613
Molecular weight:
61829.575
Reactions
Adenosine triphosphate + Pyruvic acid → ADP + Phosphoenolpyruvic aciddetails
Guanosine triphosphate + Pyruvic acid → Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Deoxyadenosine triphosphate + Pyruvic acid → dADP + Phosphoenolpyruvic aciddetails
dGTP + Pyruvic acid → dGDP + Phosphoenolpyruvic aciddetails
Nucleoside triphosphate + Pyruvic acid → NDP + Phosphoenolpyruvic aciddetails
Enzyme Details
7. Phosphoenolpyruvate carboxykinase [GTP], mitochondrial
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle (By similarity).
Gene Name:
PCK2
Uniprot ID:
Q16822
Molecular weight:
47563.34
Reactions
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Inosine triphosphate + Oxalacetic acid → IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
Enzyme Details
8. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle.
Gene Name:
PCK1
Uniprot ID:
P35558
Molecular weight:
69193.975
Reactions
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Inosine triphosphate + Oxalacetic acid → IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
9. Beta-enolase
General function:
Involved in magnesium ion binding
Specific function:
Appears to have a function in striated muscle development and regeneration.
Gene Name:
ENO3
Uniprot ID:
P13929
Molecular weight:
42248.03
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
10. Gamma-enolase
General function:
Involved in magnesium ion binding
Specific function:
Has neurotrophic and neuroprotective properties on a broad spectrum of central nervous system (CNS) neurons. Binds, in a calcium-dependent manner, to cultured neocortical neurons and promotes cell survival (By similarity).
Gene Name:
ENO2
Uniprot ID:
P09104
Molecular weight:
47268.125
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails

Transporters

Enzyme Details
1. Solute carrier organic anion transporter family member 2A1
General function:
Not Available
Specific function:
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
Molecular weight:
70117.0
References
  1. Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [PubMed:11997326 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters