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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:56 UTC

HMDB ID

HMDB0000707

Secondary Accession Numbers

HMDB00707

Metabolite Identification

Common Name

4-Hydroxyphenylpyruvic acid

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4-Hydroxyphenyl)pyruvic acid	ChEBI
(p-Hydroxyphenyl)pyruvic acid	ChEBI
3-(4-HYDROXY-phenyl)pyruvIC ACID	ChEBI
3-(4-Hydroxyphenyl)pyruvic acid	ChEBI
3-(p-Hydroxyphenyl)-2-oxopropanoic acid	ChEBI
4-Hydroxy alpha-oxobenzenepropanoic acid	ChEBI
p-Hydroxyphenylpyruvic acid	ChEBI
4-Hydroxyphenylpyruvate	Kegg
(4-Hydroxyphenyl)pyruvate	Generator
(p-Hydroxyphenyl)pyruvate	Generator
3-(4-HYDROXY-phenyl)pyruvate	Generator
3-(4-Hydroxyphenyl)pyruvate	Generator
3-(p-Hydroxyphenyl)-2-oxopropanoate	Generator
4-Hydroxy a-oxobenzenepropanoate	Generator
4-Hydroxy a-oxobenzenepropanoic acid	Generator
4-Hydroxy alpha-oxobenzenepropanoate	Generator
4-Hydroxy α-oxobenzenepropanoate	Generator
4-Hydroxy α-oxobenzenepropanoic acid	Generator
p-Hydroxyphenylpyruvate	Generator
(p-Hydroxyphenyl)-pyruvate	HMDB
(p-Hydroxyphenyl)-pyruvic acid	HMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoate	HMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoic acid	HMDB
3-(4-Hydroxyphenyl)-2-oxopropionate	HMDB
3-(4-Hydroxyphenyl)-2-oxopropionic acid	HMDB
3-(p-Hydroxyphenyl)-2-oxopropionate	HMDB
3-(p-Hydroxyphenyl)-2-oxopropionic acid	HMDB
3-(p-Hydroxyphenyl)pyruvate	HMDB
3-(p-Hydroxyphenyl)pyruvic acid	HMDB
4-Hydroxy-a-oxobenzenepropanoate	HMDB
4-Hydroxy-a-oxobenzenepropanoic acid	HMDB
4-Hydroxy-alpha-oxobenzenepropanoate	HMDB
4-Hydroxy-alpha-oxobenzenepropanoic acid	HMDB
4HPPA	HMDB
HPPA	HMDB
Hydroxyphenylpyruvate	HMDB
Hydroxyphenylpyruvic acid	HMDB
p-Hydroxyphenylpyruvic	HMDB
Testacid	HMDB
4-Hydroxyphenylpyruvic acid, ion	HMDB
4-Hydroxyphenylpyruvic acid, sodium salt	HMDB
Para-hydroxyphenylpyruvic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

3-(4-hydroxyphenyl)-2-oxopropanoic acid

Traditional Name

4-hydroxyphenylpyruvic acid

CAS Registry Number

156-39-8

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

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Phenylpyruvate
3-phenylpropanoic-acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-keto acid
Keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:15999 )
oxo carboxylic acid (CHEBI:15999 )

Ontology

Not Available

Endogenous (HMDB: HMDB0140441)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	145.746	30932474
[M-H]-	Not Available	145.746	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001915

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.69 m³·mol⁻¹	ChemAxon
Polarizability	16.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.28	31661259
DarkChem	[M+H]+	140.28	31661259
DarkChem	[M-H]-	137.786	31661259
DarkChem	[M-H]-	137.786	31661259
AllCCS	[M+H]+	138.184	32859911
AllCCS	[M-H]-	136.312	32859911
DeepCCS	[M+H]+	137.049	30932474
DeepCCS	[M-H]-	134.654	30932474
DeepCCS	[M-2H]-	169.996	30932474
DeepCCS	[M+Na]+	144.471	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	137.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC=C(O)C=C1	3200.8	Standard polar	33892256
4-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC=C(O)C=C1	1281.3	Standard non polar	33892256
4-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC=C(O)C=C1	1787.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenylpyruvic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O)C=C1	1824.8	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(=O)C(=O)O)C=C1	1839.9	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CC1=CC=C(O)C=C1)C(=O)O	2025.2	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1	1882.9	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CC1=CC=C(O)C=C1)O[Si](C)(C)C	2053.6	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2088.7	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2071.8	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2014.1	Standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2015.1	Standard polar	33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O)C=C1	2094.5	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)C(=O)O)C=C1	2121.6	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC1=CC=C(O)C=C1)C(=O)O	2278.9	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2382.7	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C	2529.5	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2596.6	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2764.6	Semi standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2665.0	Standard non polar	33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2386.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-002f-1920000000-75b07d9c09371340939f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00xr-9340000000-087aad2497b3493d27c0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 2 TMS)	splash10-002o-5910000000-fd1e55c84c79bfeca559	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 2 TMS)	splash10-002f-1941000000-2b4c87544657895fcaf6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 3 TMS)	splash10-014i-3492100000-483bdcea11d60fe4d306	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 3 TMS)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid EI-B (Non-derivatized)	splash10-002f-1951000000-ecd071a64b26ca77684c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-002f-1920000000-75b07d9c09371340939f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-00xr-9340000000-087aad2497b3493d27c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)	splash10-002o-5910000000-fd1e55c84c79bfeca559	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)	splash10-002f-1941000000-2b4c87544657895fcaf6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)	splash10-014i-3492100000-483bdcea11d60fe4d306	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-0006-2920000000-469469dfaad745fa78e8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-002o-2910000000-4f336335a2366e7dd6db	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-91bfe3ee54a36877251b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0adi-6961000000-670161f1542fda9ff1fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a59-5900000000-6c003e26816579df31ca	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0a4i-0900000000-12033042c41b550bed42	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0a4i-0900000000-6e8a3701c6d254cc824d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0560-1900000000-8082c68e259d24234d05	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-004i-0900000000-2416d7f64101b9473cbb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0a4i-2900000000-b4c21b3d9751b9e56d67	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0005-9400000000-708e258e692a0abfbc92	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-001m-9000000000-fb80dcbab23323a042af	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-2416d7f64101b9473cbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-2900000000-ad1f1fabdf6b1579fff7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOF	splash10-0005-9400000000-708e258e692a0abfbc92	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOF	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOF	splash10-001m-9000000000-fb80dcbab23323a042af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid , positive-QTOF	splash10-001i-1900000000-76ae33b45e4348d50b07	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Negative-QTOF	splash10-02bf-7900000000-665940e67ad40f759048	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Negative-QTOF	splash10-053i-9800000000-0f708ba46e75f553e77c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 35V, Negative-QTOF	splash10-00dl-5900000000-86f6d19bba9a914d22ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 35V, Positive-QTOF	splash10-0159-0900000000-a1a6bf5b3a0ac3863c90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Negative-QTOF	splash10-06ur-9700000000-18795e8a2dc93ca36a93	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Positive-QTOF	splash10-08gr-0900000000-be3cb913118057f499d1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Positive-QTOF	splash10-06rj-0900000000-6bebea0fda2ef3a2263b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Positive-QTOF	splash10-0a6r-6900000000-ede11b81a97e891c66e3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Negative-QTOF	splash10-004i-0900000000-2584f872c980915c1739	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Negative-QTOF	splash10-01s9-1900000000-249c71cfa9cefe2a8020	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Negative-QTOF	splash10-001l-3900000000-66991d861a91be9b9286	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Phenylalanine and Tyrosine Metabolism
Phenylketonuria		Not Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)		Not Available
Tyrosinemia Type 3 (TYRO3)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.37 +/- 0.23 uM	Adult (>18 years old)	Both	Normal	9106023	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	1.65 (0.15-8.74) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9869358	details
Urine	Detected and Quantified	0.66 (0.23-2.50) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9869358	details
Urine	Detected and Quantified	4.9 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	4.6 (0.1-21.3) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.8 (0.1-4.5) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.5 (0.6-3.4) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.8 (1.2-4.3) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	150.31(60.04-507.20) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	10.669 +/- 16.944 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	20.0820 +/- 49.577 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	9.413 +/- 18.199 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	12 umol/mmol creatinine	Newborn (0-30 days old)	Female	Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome	17994565	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cardiosvacular risk	Mar Garcia-A...	details
Urine	Detected and Quantified	0 - 3.4 umol/mmol creatinine	Newborn (0-30 days old)	Both	Hawkinsinuria	26226126	details
Urine	Detected and Quantified	102.8 -537.4 umol/mmol creatinine	Newborn (0-30 days old)	Both	Hawkinsinuria	26226126	details
Urine	Detected and Quantified	2.447 +/- 20.710 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	33.261 +/- 20.0820 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	24.00 +/- 30.5 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details
Urine	Detected and Quantified	33.261 +/- 26.985 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ] Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Hawkinsinuria
Thodi G, Schulpis KH, Dotsikas Y, Pavlides C, Molou E, Chatzidaki M, Triantafylli O, Loukas YL: Hawkinsinuria in two unrelated Greek newborns: identification of a novel variant, biochemical findings and treatment. J Pediatr Endocrinol Metab. 2016 Jan;29(1):15-20. doi: 10.1515/jpem-2015-0132. [PubMed:26226126 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome
James AW, Miranda SG, Culver K, Hall BD, Golabi M: DOOR syndrome: clinical report, literature review and discussion of natural history. Am J Med Genet A. 2007 Dec 1;143A(23):2821-31. doi: 10.1002/ajmg.a.32054. [PubMed:17994565 ]

Associated OMIM IDs

114500 (Colorectal cancer)
261600 (Phenylketonuria)
140350 (Hawkinsinuria)
220500 (Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome)

External Links

DrugBank ID

DB07718

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

P-HYDROXY-PHENYLPYRUVATE

BiGG ID

37006

Wikipedia Link

4-Hydroxyphenylpyruvic_acid

METLIN ID

5675

PubChem Compound

979

PDB ID

Not Available

ChEBI ID

15999

Food Biomarker Ontology

Not Available

VMH ID

34HPP

MarkerDB ID

MDB00000229

Good Scents ID

Not Available

References

Synthesis Reference

Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tomoeda K, Awata H, Matsuura T, Matsuda I, Ploechl E, Milovac T, Boneh A, Scott CR, Danks DM, Endo F: Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria. Mol Genet Metab. 2000 Nov;71(3):506-10. [PubMed:11073718 ]
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 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Endo F, Katoh H, Yamamoto S, Matsuda I: A murine model for type III tyrosinemia: lack of immunologically detectable 4-hydroxyphenylpyruvic acid dioxygenase enzyme protein in a novel mouse strain with hypertyrosinemia. Am J Hum Genet. 1991 Apr;48(4):704-9. [PubMed:2014797 ]
Shoda J, Tanaka N, Osuga T, Matsuura K, Miyazaki H: Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine. J Lipid Res. 1990 Feb;31(2):249-59. [PubMed:2324645 ]
Wolff JA, Barshop B, Nyhan WL, Leslie J, Seegmiller JE, Gruber H, Garst M, Winter S, Michals K, Matalon R: Effects of ascorbic acid in alkaptonuria: alterations in benzoquinone acetic acid and an ontogenic effect in infancy. Pediatr Res. 1989 Aug;26(2):140-4. [PubMed:2771520 ]
Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG, de Vries JA: Determination of 3-methoxy-4-hydroxyphenylpyruvic acid, 3,4-dihydroxyphenylethylene glycol, and 3,4-dihydroxyphenylmandelic acid in urine by mass fragmentography, with use of deuterium-labeled internal standards. Clin Chem. 1978 Nov;24(11):2001-8. [PubMed:709835 ]
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 ]

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

4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid	details

Enzyme Details

2. Tyrosine aminotransferase

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:: TAT
Uniprot ID:: P17735
Molecular weight:: 50398.895

Reactions

L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details

Enzyme Details

3. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details

Enzyme Details

4. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details

Enzyme Details

5. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-Hydroxyphenylpyruvic acid → 6-[4-(2-carboxy-2-oxoethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
4-Hydroxyphenylpyruvic acid → 3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-2-oxopropanoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

6. 4-hydroxyphenylpyruvate dioxygenase

General function:: Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:: Key enzyme in the degradation of tyrosine.
Gene Name:: HPD
Uniprot ID:: P32754
Molecular weight:: 40497.105

Reactions

4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + CO(2)	details
4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + Carbon dioxide	details

Enzyme Details

7. L-amino-acid oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:: IL4I1
Uniprot ID:: Q96RQ9
Molecular weight:: 65327.26

Reactions

L-Tyrosine + Water + Oxygen → 4-Hydroxyphenylpyruvic acid + Ammonia + Hydrogen peroxide	details

Enzyme Details

8. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4-Hydroxyphenylpyruvic acid → 2-oxo-3-[4-(sulfooxy)phenyl]propanoic acid	details

Showing metabocard for 4-Hydroxyphenylpyruvic acid (HMDB0000707)

MOL for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

3D MOL for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

3D SDF for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

3D-SDF for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

PDB for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

3D PDB for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

SMILES for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

INCHI for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

Structure for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

3D Structure for HMDB0000707 (4-Hydroxyphenylpyruvic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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