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Showing metabocard for 2-Oxo-3-hydroxy-4-phosphobutanoic acid (HMDB0006801)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:13:41 UTC
Update Date2021-09-14 15:00:11 UTC
HMDB IDHMDB0006801
Secondary Accession Numbers
  • HMDB06801
Metabolite Identification
Common Name2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description2-Oxo-3-hydroxy-4-phosphobutanoic acid, also known as (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate or alpha-keto-3-hydroxy-4-phosphobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Oxo-3-hydroxy-4-phosphobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Oxo-3-hydroxy-4-phosphobutanoic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Oxo-3-hydroxy-4-phosphobutanoic acid has been detected, but not quantified in, several different foods, such as peanuts, breakfast cereals, kai-lans, common beans, and cardoons. This could make 2-oxo-3-hydroxy-4-phosphobutanoic acid a potential biomarker for the consumption of these foods. A 2-oxo monocarboxylic acid that is 2-oxobutanoic acid which is substituted by a phosphonooxy group at position 4 and a hydroxy group at the 3-pro-R position.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

  Mrv1652309042000322D          

 13 12  0  0  1  0            999 V2000
   14.8418   -9.3553    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0130   -9.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6706   -9.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8381   -8.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8381  -10.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3017   -9.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5863   -9.3591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8787   -9.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5826   -8.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1596   -9.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8750  -10.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4444   -9.7678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559   -8.5304    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  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  8 10  1  0  0  0  0
  8 11  2  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
M  END
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3D MOL for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

HMDB0006801
     RDKit          3D
2-Oxo-3-hydroxy-4-phosphobutanoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    1.7106    1.7397    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679    0.9769   -0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223    1.6017   -1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727   -0.4540   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5119   -1.1257   -1.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634   -1.1522    0.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3359   -2.5450    0.3171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3349   -0.8386    0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5078    0.4992    0.4848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713    1.0424    0.3764 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0388    2.5569    0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.7427    1.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.3486   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    2.3696   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.8848    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -3.0566    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471   -1.4699    1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -1.1611   -0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.1898    1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8165    0.9999   -1.7065 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
  3 14  1  0
  6 15  1  1
  7 16  1  0
  8 17  1  0
  8 18  1  0
 12 19  1  0
 13 20  1  0
M  END
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3D SDF for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

  Mrv1652309042000322D          

 13 12  0  0  1  0            999 V2000
   14.8418   -9.3553    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0130   -9.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6706   -9.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8381   -8.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8381  -10.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3017   -9.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5863   -9.3591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8787   -9.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5826   -8.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1596   -9.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8750  -10.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4444   -9.7678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559   -8.5304    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  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  8 10  1  0  0  0  0
  8 11  2  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006801

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H](COP(O)(O)=O)C(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2,5H,1H2,(H,7,8)(H2,9,10,11)/t2-/m1/s1

> <INCHI_KEY>
MZJFVXDTNBHTKZ-UWTATZPHSA-N

> <FORMULA>
C4H7O8P

> <MOLECULAR_WEIGHT>
214.0673

> <EXACT_MASS>
213.987853712

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.260088660826515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-2.01

> <JCHEM_LOGP>
-1.3530858483333335

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.775362844628003

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3366600113332643

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9601866599060154

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
36.602399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

HMDB0006801
     RDKit          3D
2-Oxo-3-hydroxy-4-phosphobutanoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    1.7106    1.7397    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679    0.9769   -0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223    1.6017   -1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727   -0.4540   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5119   -1.1257   -1.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634   -1.1522    0.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3359   -2.5450    0.3171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3349   -0.8386    0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5078    0.4992    0.4848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713    1.0424    0.3764 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0388    2.5569    0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    0.7427    1.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.3486   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    2.3696   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.8848    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -3.0566    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471   -1.4699    1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -1.1611   -0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.1898    1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8165    0.9999   -1.7065 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
  3 14  1  0
  6 15  1  1
  7 16  1  0
  8 17  1  0
  8 18  1  0
 12 19  1  0
 13 20  1  0
M  END
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PDB for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

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  P   UNK     0      27.705 -17.463   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      26.158 -17.463   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.252 -17.463   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      27.698 -15.916   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.698 -19.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      24.830 -18.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.494 -17.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.174 -18.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.488 -15.923   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      20.831 -17.470   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.167 -19.780   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      19.496 -18.233   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      20.824 -15.923   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8   12   13                                                  
CONECT   11    8                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

COMPND    HMDB0006801
HETATM    1  O1  UNL     1       1.711   1.740   0.365  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.168   0.977  -0.512  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.922   1.602  -1.520  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.973  -0.454  -0.547  1.00  0.00           C  
HETATM    5  O3  UNL     1       2.512  -1.126  -1.468  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.163  -1.152   0.464  1.00  0.00           C  
HETATM    7  O4  UNL     1       1.336  -2.545   0.317  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.335  -0.839   0.333  1.00  0.00           C  
HETATM    9  O5  UNL     1      -0.508   0.499   0.485  1.00  0.00           O  
HETATM   10  P1  UNL     1      -2.071   1.042   0.376  1.00  0.00           P  
HETATM   11  O6  UNL     1      -2.039   2.557   0.191  1.00  0.00           O  
HETATM   12  O7  UNL     1      -2.992   0.743   1.754  1.00  0.00           O  
HETATM   13  O8  UNL     1      -2.803   0.349  -0.979  1.00  0.00           O  
HETATM   14  H1  UNL     1       2.455   2.370  -1.986  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.502  -0.885   1.465  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.641  -3.057   0.773  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.847  -1.470   1.086  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.651  -1.161  -0.695  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.321  -0.190   1.804  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.817   1.000  -1.707  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5    6
CONECT    6    7    8   15
CONECT    7   16
CONECT    8    9   17   18
CONECT    9   10
CONECT   10   11   11   12   13
CONECT   12   19
CONECT   13   20
END
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SMILES for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

O[C@H](COP(O)(O)=O)C(=O)C(O)=O
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INCHI for HMDB0006801 (2-Oxo-3-hydroxy-4-phosphobutanoic acid)

InChI=1S/C4H7O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2,5H,1H2,(H,7,8)(H2,9,10,11)/t2-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoateChEBI
2-oxo-3-Hydroxy-4-phosphobutanoateChEBI
alpha-Keto-3-hydroxy-4-phosphobutyrateChEBI
(3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoateKegg
(3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoic acidGenerator
a-Keto-3-hydroxy-4-phosphobutyrateGenerator
a-Keto-3-hydroxy-4-phosphobutyric acidGenerator
alpha-Keto-3-hydroxy-4-phosphobutyric acidGenerator
Α-keto-3-hydroxy-4-phosphobutyrateGenerator
Α-keto-3-hydroxy-4-phosphobutyric acidGenerator
(3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoic acidGenerator
Chemical FormulaC4H7O8P
Average Molecular Weight214.0673
Monoisotopic Molecular Weight213.987853712
IUPAC Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Traditional Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
CAS Registry NumberNot Available
SMILES
O[C@H](COP(O)(O)=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C4H7O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2,5H,1H2,(H,7,8)(H2,9,10,11)/t2-/m1/s1
InChI KeyMZJFVXDTNBHTKZ-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain keto acid
  • Beta-hydroxy acid
  • Acyloin
  • Alpha-keto acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
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
Predicted Chromatographic Properties
Spectra
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030351
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06054
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21145142
PDB IDNot Available
ChEBI ID27951
Food Biomarker OntologyNot Available
VMH IDNot Available
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. Phosphoserine aminotransferase
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
Reactions
O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid → 2-Oxo-3-hydroxy-4-phosphobutanoic acid + Glutamic aciddetails