Showing metabocard for 4-Hydroxyphenylpyruvic acid (MMDBc0000535)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:58 UTC
Update Date2024-10-09 22:37:07 UTC
Metabolite IDMMDBc0000535
Metabolite Identification
Common Name4-Hydroxyphenylpyruvic acid
Description4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase (EC 1.1.1.222) and is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718 ). Moreover, 4-hydroxyphenylpyruvic acid is also found to be associated in phenylketonuria, which is also an inborn error of metabolism. There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. 4-HPPA has been found to be a microbial metabolite in Escherichia (ECMDB).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f920d5e5de8>


  Mrv1652309042000062D          

 13 13  0  0  0  0            999 V2000
   12.2744   -7.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2744   -8.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -7.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -8.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8455   -7.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8455   -8.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -6.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2743   -5.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2743   -5.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -6.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -7.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7033   -5.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -9.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f920d5e5de8>

HMDB0000707
     RDKit          3D
4-Hydroxyphenylpyruvic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0731   -0.4994   -0.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226    0.0246    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.5321    1.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828    0.0936    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5239    0.6135    1.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443   -0.4626   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021   -0.3070   -0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -1.2572    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -1.0596    0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325    0.0707    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.2267    0.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    1.0180   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365    0.8359   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.4915    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537    0.0321   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601   -1.5680   -0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341   -2.1476    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -1.8021    1.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251    0.6685    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    1.9125   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499    1.5836   -1.2357 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  7  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f920d5e5de8>


  Mrv1652309042000062D          

 13 13  0  0  0  0            999 V2000
   12.2744   -7.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2744   -8.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -7.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -8.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8455   -7.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8455   -8.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -6.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2743   -5.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2743   -5.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -6.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -7.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7033   -5.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -9.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000535

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

> <INCHI_KEY>
KKADPXVIOXHVKN-UHFFFAOYSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.750960680327967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxyphenyl)-2-oxopropanoic acid

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.596648451333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.498853206830276

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.91496710599853

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958513128269975

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
44.6925

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyphenylpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f920d5e5de8>

HMDB0000707
     RDKit          3D
4-Hydroxyphenylpyruvic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0731   -0.4994   -0.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226    0.0246    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.5321    1.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828    0.0936    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5239    0.6135    1.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443   -0.4626   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021   -0.3070   -0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -1.2572    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -1.0596    0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325    0.0707    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.2267    0.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    1.0180   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365    0.8359   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.4915    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537    0.0321   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601   -1.5680   -0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341   -2.1476    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -1.8021    1.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251    0.6685    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    1.9125   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499    1.5836   -1.2357 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  7  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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PDB for #<Metabolite:0x00007f920d5e5de8>

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      22.912 -14.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.912 -15.743   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.578 -13.433   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.578 -16.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.245 -14.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.245 -15.743   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.578 -11.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.912 -11.123   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      22.912  -9.583   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.246 -11.893   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      24.246 -13.433   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.579 -11.123   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      21.578 -18.053   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    6   13                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f920d5e5de8>

COMPND    HMDB0000707
HETATM    1  O1  UNL     1       4.073  -0.499  -0.572  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.523   0.025   0.427  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.365   0.532   1.415  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.083   0.094   0.537  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.524   0.613   1.528  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.244  -0.463  -0.546  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.202  -0.307  -0.269  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.940  -1.257   0.405  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.276  -1.060   0.633  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.932   0.071   0.211  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.284   0.227   0.464  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.190   1.018  -0.463  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.837   0.836  -0.704  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.696   1.491   1.420  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.554   0.032  -1.487  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.460  -1.568  -0.605  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.434  -2.148   0.741  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.871  -1.802   1.165  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.625   0.669   1.299  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.681   1.913  -0.805  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.250   1.584  -1.236  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5    6
CONECT    6    7   15   16
CONECT    7    8    8   13
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11   12
CONECT   11   19
CONECT   12   13   13   20
CONECT   13   21
END
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SMILES for #<Metabolite:0x00007f920d5e5de8>

OC(=O)C(=O)CC1=CC=C(O)C=C1
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INCHI for #<Metabolite:0x00007f920d5e5de8>

InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
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Synonyms
ValueSource
(4-Hydroxyphenyl)pyruvic acidChEBI
(p-Hydroxyphenyl)pyruvic acidChEBI
3-(4-HYDROXY-phenyl)pyruvIC ACIDChEBI
3-(4-Hydroxyphenyl)pyruvic acidChEBI
3-(p-Hydroxyphenyl)-2-oxopropanoic acidChEBI
4-Hydroxy alpha-oxobenzenepropanoic acidChEBI
p-Hydroxyphenylpyruvic acidChEBI
4-HydroxyphenylpyruvateKegg
(4-Hydroxyphenyl)pyruvateGenerator
(p-Hydroxyphenyl)pyruvateGenerator
3-(4-HYDROXY-phenyl)pyruvateGenerator
3-(4-Hydroxyphenyl)pyruvateGenerator
3-(p-Hydroxyphenyl)-2-oxopropanoateGenerator
4-Hydroxy a-oxobenzenepropanoateGenerator
4-Hydroxy a-oxobenzenepropanoic acidGenerator
4-Hydroxy alpha-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoic acidGenerator
p-HydroxyphenylpyruvateGenerator
(p-Hydroxyphenyl)-pyruvateHMDB
(p-Hydroxyphenyl)-pyruvic acidHMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoateHMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoic acidHMDB
3-(4-Hydroxyphenyl)-2-oxopropionateHMDB
3-(4-Hydroxyphenyl)-2-oxopropionic acidHMDB
3-(p-Hydroxyphenyl)-2-oxopropionateHMDB
3-(p-Hydroxyphenyl)-2-oxopropionic acidHMDB
3-(p-Hydroxyphenyl)pyruvateHMDB
3-(p-Hydroxyphenyl)pyruvic acidHMDB
4-Hydroxy-a-oxobenzenepropanoateHMDB
4-Hydroxy-a-oxobenzenepropanoic acidHMDB
4-Hydroxy-alpha-oxobenzenepropanoateHMDB
4-Hydroxy-alpha-oxobenzenepropanoic acidHMDB
4HPPAHMDB
HPPAHMDB
HydroxyphenylpyruvateHMDB
Hydroxyphenylpyruvic acidHMDB
p-HydroxyphenylpyruvicHMDB
TestacidHMDB
4-Hydroxyphenylpyruvic acid, ionHMDB
4-Hydroxyphenylpyruvic acid, sodium saltHMDB
Para-hydroxyphenylpyruvic acidHMDB
Molecular FormulaC9H8O4
Average Mass180.1574
Monoisotopic Mass180.042258744
IUPAC Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Traditional Name4-hydroxyphenylpyruvic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
InChI KeyKKADPXVIOXHVKN-UHFFFAOYSA-N