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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-02-28 20:23:00 UTC

Update Date

2023-02-21 17:33:47 UTC

HMDB ID

HMDB0240257

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Quinolacetic acid

Description

Quinolacetic acid is a by-product of the partially defective enzyme, 4-hydroxyphenylpyruvate dioxygenase (PMID: 6619234 ). When present in sufficiently high levels, quinolacetic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of quinolacetic acid are associated with hawkinsinuria (PMID: 6619234 ). Hawkinsinuria is characterized by the inability to break down the amino acid tyrosine. The features of this condition usually appear around the time infants are weaned off breast milk and begin to use formula. The signs and symptoms may include the following: failure to gain weight and grow at the expected rate (failure to thrive), abnormally high acid levels in the blood (acidosis), and fine or sparse hair. Hawkinsin is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated hawkinsinuria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.

Structure

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

HEADER    PROTEIN                                 28-FEB-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-FEB-18         0                                  
HETATM    1  C   UNK     0    8669.1898669.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.5238668.234   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8671.8588669.003   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.5238666.695   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.8578669.772   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.8608665.927   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.5268669.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1928668.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.1928666.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.5268665.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8608666.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.8608668.235   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   12                                                            
CONECT    6    9                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    5    1                                             
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
Quinolacetate	Generator

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

IUPAC Name

2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

Traditional Name

(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

CAS Registry Number

55604-87-0

SMILES

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

InChI Identifier

InChI=1S/C8H8O4/c9-6-1-3-8(12,4-2-6)5-7(10)11/h1-4,12H,5H2,(H,10,11)

InChI Key

RFJUCKOEXRTZPN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240257)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-0.2	ALOGPS
logP	0.048	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-3.4	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	2	ChemAxon
Refractivity	42.47 m³·mol⁻¹	ChemAxon
Polarizability	15.02 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
AllCCS	[M-H]-	132.954	31661259
AllCCS	[M+H]+	135.958	31661259
DeepCCS	[M+H]+	136.02	30932474
DeepCCS	[M-H]-	133.251	30932474
DeepCCS	[M-2H]-	169.439	30932474
DeepCCS	[M+Na]+	144.734	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.47 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8545 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	821.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	67.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	337.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	369.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	627.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	969.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	731.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	275.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	235.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinolacetic acid	OC(=O)CC1(O)C=CC(=O)C=C1	3072.2	Standard polar	33892256
Quinolacetic acid	OC(=O)CC1(O)C=CC(=O)C=C1	1300.9	Standard non polar	33892256
Quinolacetic acid	OC(=O)CC1(O)C=CC(=O)C=C1	1605.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinolacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(O)C=CC(=O)C=C1	1661.0	Semi standard non polar	33892256
Quinolacetic acid,1TMS,isomer #2	C[Si](C)(C)OC1(CC(=O)O)C=CC(=O)C=C1	1758.2	Semi standard non polar	33892256
Quinolacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(O[Si](C)(C)C)C=CC(=O)C=C1	1800.4	Semi standard non polar	33892256
Quinolacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(O)C=CC(=O)C=C1	1938.2	Semi standard non polar	33892256
Quinolacetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1(CC(=O)O)C=CC(=O)C=C1	2011.3	Semi standard non polar	33892256
Quinolacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(O[Si](C)(C)C(C)(C)C)C=CC(=O)C=C1	2258.7	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 - Quinolacetic 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 - Quinolacetic acid 10V, Positive-QTOF	splash10-0zfr-0900000000-b74e59f3f97c304eeeec	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 20V, Positive-QTOF	splash10-0a4i-0900000000-f9b2555f2482f77e5247	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 40V, Positive-QTOF	splash10-057i-9100000000-2a88148606d5002a77ed	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 10V, Negative-QTOF	splash10-00xr-0900000000-c796bc9c0c0b00401b98	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 20V, Negative-QTOF	splash10-0601-0900000000-695ee30579653a8efd2a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 40V, Negative-QTOF	splash10-0a4j-9800000000-18e8d652c4fb6f0f7043	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 10V, Negative-QTOF	splash10-06dj-0900000000-7efa0d0f69626d635cb0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 20V, Negative-QTOF	splash10-0a4i-1900000000-39081639d57ec836aef1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 40V, Negative-QTOF	splash10-0a6r-9600000000-6c1bc32765f590952b1e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 10V, Positive-QTOF	splash10-0pw9-0900000000-dd348ad9926ba5235968	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 20V, Positive-QTOF	splash10-0a4i-3900000000-a012b8b9b41e080c409e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinolacetic acid 40V, Positive-QTOF	splash10-0pbc-9200000000-262583d9338784273088	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4955602

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quinolacetic acid

METLIN ID

Not Available

PubChem Compound

Not Available

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

Hocart CH, Halpern B, Hick LA, Wong CO: Hawkinsinuria--identification of quinolacetic acid and pyroglutamic acid during an acidotic phase. J Chromatogr. 1983 Jul 8;275(2):237-43. [PubMed:6619234 ]

Showing metabocard for Quinolacetic acid (HMDB0240257)

MOL for HMDB0240257 (Quinolacetic acid)

3D MOL for HMDB0240257 (Quinolacetic acid)

3D SDF for HMDB0240257 (Quinolacetic acid)

3D-SDF for HMDB0240257 (Quinolacetic acid)

PDB for HMDB0240257 (Quinolacetic acid)

3D PDB for HMDB0240257 (Quinolacetic acid)

SMILES for HMDB0240257 (Quinolacetic acid)

INCHI for HMDB0240257 (Quinolacetic acid)

Structure for HMDB0240257 (Quinolacetic acid)

3D Structure for HMDB0240257 (Quinolacetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra