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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2023-02-21 17:16:21 UTC

HMDB ID

HMDB0002334

Secondary Accession Numbers

HMDB02334

Metabolite Identification

Common Name

Benzoquinoneacetic acid

Description

Benzoquinoneacetic acid (BQA) is an oxidized form of homogentisic acid. The oxidation of homogentisic acid to BQA is catalyzed by the enzyme polyphenol oxidase. BQA is secreted in high quantities in the urine of patients suffering from cyanosis caused by vitamin C deficiency (Ella H. Fishberg, J. Biol. Chem., Jan 1948; 172: 155 - 163). Cyanosis is the bluish colouration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. When present in sufficiently high levels, BQA can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of BQA are associated with alkaptonuria (OMIM: 203500 ), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of both homogentisic acid and BQA in the blood and tissues. When excreted in the urine, these compounds give it an unusually dark color. The accumulating BQA causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, BQA can form polymers that resemble the dark skin pigment melanin. These are deposited in collagen, especially in tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage.

Structure

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

HEADER    PROTEIN                                 21-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:             3-Hydroxyphenylglycine.mol            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-18         0                                  
HETATM    1  C   UNK     0      -3.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.001   3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.001  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.334   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Benzoquinoneacetate	Generator
BQA	HMDB
Benzoquinone acetic acid	HMDB
2-(3,6-Dioxocyclohexa-1,4-dien-1-yl)acetate	Generator, HMDB

Chemical Formula

C₈H₆O₄

Average Molecular Weight

166.1308

Monoisotopic Molecular Weight

166.02660868

IUPAC Name

2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid

Traditional Name

benzoquinoneacetic acid

CAS Registry Number

10275-07-7

SMILES

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

InChI Identifier

InChI=1S/C8H6O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)

InChI Key

RAPRJRLALQKSHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002334)

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

Indirect biological role

Metabotoxin

Osteotoxin (HMDB: HMDB0002334)

Renal toxin (HMDB: HMDB0002334)

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	5.46 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.54	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-8.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.65 m³·mol⁻¹	ChemAxon
Polarizability	14.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	138.192	31661259
DarkChem	[M-H]-	132.631	31661259
DeepCCS	[M+H]+	132.206	30932474
DeepCCS	[M-H]-	128.412	30932474
DeepCCS	[M-2H]-	165.805	30932474
DeepCCS	[M+Na]+	141.322	30932474
AllCCS	[M+H]+	134.7	32859911
AllCCS	[M+H-H2O]+	130.3	32859911
AllCCS	[M+NH4]+	138.8	32859911
AllCCS	[M+Na]+	139.9	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoquinoneacetic acid	OC(=O)CC1=CC(=O)C=CC1=O	2883.4	Standard polar	33892256
Benzoquinoneacetic acid	OC(=O)CC1=CC(=O)C=CC1=O	1303.2	Standard non polar	33892256
Benzoquinoneacetic acid	OC(=O)CC1=CC(=O)C=CC1=O	1511.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoquinoneacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(=O)C=CC1=O	1772.4	Semi standard non polar	33892256
Benzoquinoneacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(=O)C=CC1=O	2027.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-51321079231d86b295a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8920000000-6c81edffefa422ba173a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoquinoneacetic 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 - Benzoquinoneacetic acid 10V, Positive-QTOF	splash10-0002-0900000000-fa130465e081632f69f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Positive-QTOF	splash10-00dj-4900000000-cd386239c5244d6527df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Positive-QTOF	splash10-0690-9000000000-db1f626a086c73a6579e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Negative-QTOF	splash10-01b9-0900000000-8b51337fe9bfda05eb61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Negative-QTOF	splash10-00xs-0900000000-9afdadb1210637bd69a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Negative-QTOF	splash10-014j-9700000000-6f354928322b23cc865b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Negative-QTOF	splash10-00di-0900000000-a28fdef9c1c00d45c3ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Negative-QTOF	splash10-00di-0900000000-6a3b331dfd30a9e6f27b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Negative-QTOF	splash10-00xu-9500000000-a79dd2db908026733181	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Positive-QTOF	splash10-00di-0900000000-c9641136c29dd5040863	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Positive-QTOF	splash10-00di-2900000000-ee5a7e2a4027680d79ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Positive-QTOF	splash10-0l6u-9300000000-52241a6448ab82fb7f18	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB022966

KNApSAcK ID

Not Available

Chemspider ID

13628337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6628

PubChem Compound

21252288

PDB ID

Not Available

ChEBI ID

Not Available

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

Martin JP Jr, Batkoff B: Homogentisic acid autoxidation and oxygen radical generation: implications for the etiology of alkaptonuric arthritis. Free Radic Biol Med. 1987;3(4):241-50. [PubMed:3121448 ]
(). FISHBERG EH. Excretion of benzoquinoneacetic acid in hypovitaminosis C. J Biol Chem. 1948 Jan;172(1):155-63.. .

Showing metabocard for Benzoquinoneacetic acid (HMDB0002334)

MOL for HMDB0002334 (Benzoquinoneacetic acid)

3D MOL for HMDB0002334 (Benzoquinoneacetic acid)

3D SDF for HMDB0002334 (Benzoquinoneacetic acid)

3D-SDF for HMDB0002334 (Benzoquinoneacetic acid)

PDB for HMDB0002334 (Benzoquinoneacetic acid)

3D PDB for HMDB0002334 (Benzoquinoneacetic acid)

SMILES for HMDB0002334 (Benzoquinoneacetic acid)

INCHI for HMDB0002334 (Benzoquinoneacetic acid)

Structure for HMDB0002334 (Benzoquinoneacetic acid)

3D Structure for HMDB0002334 (Benzoquinoneacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra