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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-02-03 11:38:44 UTC

Update Date

2023-02-21 17:17:32 UTC

HMDB ID

HMDB0011663

Secondary Accession Numbers

HMDB11663

Metabolite Identification

Common Name

3-Hydroxyphenylpyruvic acid

Description

3-Hydroxyphenylpyruvic acid 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. 3-Hydroxyphenylpyruvic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyphenylpyruvic acid a potential biomarker for the consumption of these foods. 3-Hydroxyphenylpyruvic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 3-Hydroxyphenylpyruvic acid.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      23.745 -15.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.745 -16.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.412 -14.305   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.412 -17.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.078 -15.075   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.078 -16.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.079 -14.305   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.413 -15.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.746 -14.305   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      29.080 -15.075   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.746 -12.765   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.413 -16.615   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.744 -14.305   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6   13                                                  
CONECT    6    4    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-Hydroxyphenyl)pyruvic acid	ChEBI
3-(3-Hydroxyphenyl)pyruvic acid	ChEBI
m-Hydroxyphenylpyruvic acid	ChEBI
(3-Hydroxyphenyl)pyruvate	Generator
3-(3-Hydroxyphenyl)pyruvate	Generator
m-Hydroxyphenylpyruvate	Generator
3-Hydroxyphenylpyruvate	Generator
3-HPPA	HMDB
HPPA	HMDB
3-(3-Hydroxyphenyl)-2-oxopropanoate	Generator, HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC(=O)C(=O)CC1=CC(O)=CC=C1

InChI Identifier

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

InChI Key

PNYWALDMLUDDTA-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-4-unsubstituted benzenoid
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 oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0011663)

Source

Endogenous

Endogenous (HMDB: HMDB0011663)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.58 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.92	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	16.71 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]+	139.716	31661259
DarkChem	[M-H]-	137.075	31661259
DeepCCS	[M+H]+	136.479	30932474
DeepCCS	[M-H]-	134.083	30932474
DeepCCS	[M-2H]-	169.146	30932474
DeepCCS	[M+Na]+	143.774	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	135.1	32859911
AllCCS	[M+Na-2H]-	135.8	32859911
AllCCS	[M+HCOO]-	136.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC(O)=CC=C1	3108.7	Standard polar	33892256
3-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC(O)=CC=C1	1318.1	Standard non polar	33892256
3-Hydroxyphenylpyruvic acid	OC(=O)C(=O)CC1=CC(O)=CC=C1	1774.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyphenylpyruvic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O)=C1	1827.2	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(CC(=O)C(=O)O)=C1	1824.5	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CC1=CC=CC(O)=C1)C(=O)O	2027.4	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O[Si](C)(C)C)=C1	1843.0	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O)=C1)O[Si](C)(C)C	2017.9	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O	2012.8	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C	1971.4	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C	1971.9	Standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C	2010.3	Standard polar	33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O)=C1	2074.4	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(CC(=O)C(=O)O)=C1	2092.4	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC(O)=C1)C(=O)O	2270.5	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2308.0	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O)=C1)O[Si](C)(C)C(C)(C)C	2475.6	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	2513.3	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C	2695.6	Semi standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C	2599.8	Standard non polar	33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C	2376.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-3e796fc078a687260252	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9263000000-d009962460fe24b3edca	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Positive-QTOF	splash10-08gi-0900000000-5171586bb26270378b0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Positive-QTOF	splash10-0bti-0900000000-a3e31c3a3ec99981e3b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Positive-QTOF	splash10-0ar0-9500000000-a09621182baf2308966d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Negative-QTOF	splash10-004i-0900000000-e3b2343ff52f84dc8c77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Negative-QTOF	splash10-055r-0900000000-11559808da8e96b47aee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Negative-QTOF	splash10-053u-2900000000-5ab865fb05a4a105f202	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Negative-QTOF	splash10-004i-0900000000-93c192f24a5e54d2f8a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Negative-QTOF	splash10-053r-0900000000-45f821a4209221c59097	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Negative-QTOF	splash10-05mo-9600000000-d80adc267578ae9bcbc0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Positive-QTOF	splash10-0540-0900000000-f467cd1fa4b70f39c5d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Positive-QTOF	splash10-0a4i-3900000000-fd42a0fec8859b5c5289	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Positive-QTOF	splash10-05ox-9400000000-4094ab5b8d1dd3b9c579	2021-09-24	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

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cardiosvacular risk	Mar Garcia-A...	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028354

KNApSAcK ID

Not Available

Chemspider ID

4476924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxyphenylpyruvic acid

METLIN ID

Not Available

PubChem Compound

5318321

PDB ID

Not Available

ChEBI ID

167870

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Hydroxyphenylpyruvic acid (HMDB0011663)

MOL for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

3D MOL for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

3D SDF for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

3D-SDF for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

PDB for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

3D PDB for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

SMILES for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

INCHI for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

Structure for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

3D Structure for HMDB0011663 (3-Hydroxyphenylpyruvic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra