Showing metabocard for Phosphoenolpyruvic acid (MMDBc0029487)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:24:17 UTC
Update Date2024-10-15 19:59:53 UTC
Metabolite IDMMDBc0029487
Metabolite Identification
Common NamePhosphoenolpyruvic acid
DescriptionPhosphoenolpyruvate (PEP) plays a key role in many metabolic reactions. 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb71235f38>


  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 #<Metabolite:0x00007fdb71235f38>

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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3D SDF for #<Metabolite:0x00007fdb71235f38>


  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>
MMDBc0029487

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fdb71235f38>

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 #<Metabolite:0x00007fdb71235f38>

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 #<Metabolite:0x00007fdb71235f38>

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 #<Metabolite:0x00007fdb71235f38>

OC(=O)C(=C)OP(O)(O)=O
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INCHI for #<Metabolite:0x00007fdb71235f38>

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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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
Molecular FormulaC3H5O6P
Average Mass168.042
Monoisotopic Mass167.982374404
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