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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:29:07 UTC

Update Date

2021-09-26 22:55:34 UTC

HMDB ID

HMDB0246466

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxyquinoline

Description

quinolin-4-ol, also known as 4-chinolinol or kynurine, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Based on a literature review a significant number of articles have been published on quinolin-4-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-hydroxyquinoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Hydroxyquinoline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Chinolinol	ChEBI
4-Hydroxyquinoline	ChEBI
4-Quinolinol	ChEBI
Kynurine	ChEBI

Chemical Formula

C₉H₇NO

Average Molecular Weight

145.158

Monoisotopic Molecular Weight

145.052763851

IUPAC Name

1,4-dihydroquinolin-4-one

Traditional Name

4(1H)-quinolinone

CAS Registry Number

Not Available

SMILES

O=C1C=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)

InChI Key

PMZDQRJGMBOQBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyquinoline (CHEBI:15815 )
a small molecule (QUINOLIN-4-OL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	1.03	ALOGPS
logP	1.95	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.36	ChemAxon
pKa (Strongest Basic)	0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.02 m³·mol⁻¹	ChemAxon
Polarizability	14.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	163.181	30932474
DeepCCS	[M+Na]+	138.479	30932474
AllCCS	[M+H]+	128.0	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	126.9	32859911
AllCCS	[M+HCOO]-	127.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.5237 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1149.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	257.6 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	306.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	371.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	612.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	205.1 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	754.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	616.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.4 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	92.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyquinoline	O=C1C=CNC2=CC=CC=C12	2129.0	Standard polar	33892256
4-Hydroxyquinoline	O=C1C=CNC2=CC=CC=C12	1484.6	Standard non polar	33892256
4-Hydroxyquinoline	O=C1C=CNC2=CC=CC=C12	1974.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyquinoline,1TMS,isomer #1	C[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	1762.1	Semi standard non polar	33892256
4-Hydroxyquinoline,1TMS,isomer #1	C[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	1824.5	Standard non polar	33892256
4-Hydroxyquinoline,1TMS,isomer #1	C[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	2025.7	Standard polar	33892256
4-Hydroxyquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	1968.0	Semi standard non polar	33892256
4-Hydroxyquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	1995.7	Standard non polar	33892256
4-Hydroxyquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=CC(=O)C2=CC=CC=C21	2159.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-1900000000-5d1df582bb90a0e5db81	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyquinoline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 35V, Positive-QTOF	splash10-0002-1900000000-c74642859f5b90574b99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 50V, Positive-QTOF	splash10-014i-0900000000-32f05b60c64fe39bc2e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 50V, Positive-QTOF	splash10-0002-0900000000-c4e025e22f50afd418a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-ba7f9400cfd60a359f94	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-775d779427d7b2533266	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 50V, Positive-QTOF	splash10-0002-3900000000-a2dd2303a45c6f7142e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-b19cd7a5a023572c199a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Positive-QTOF	splash10-0002-4900000000-4e71df4b5a1a920fea22	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Negative-QTOF	splash10-0006-0900000000-1db1677337713e3a2547	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 35V, Negative-QTOF	splash10-0gbc-5900000000-82bd2e751fd456125318	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Negative-QTOF	splash10-0006-0900000000-c8e530ea0a6b88d7fc28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Negative-QTOF	splash10-0006-0900000000-74b748a465bce5c5bc48	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 40V, Positive-QTOF	splash10-00kb-0900000000-e712e973146287c97293	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Negative-QTOF	splash10-0006-1900000000-f3447fc55f04b7bf2249	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 20V, Positive-QTOF	splash10-0002-0900000000-c735e5b0cf2fc2d2cd1b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Negative-QTOF	splash10-0006-0900000000-5e412f5ec971b79b062a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Negative-QTOF	splash10-0006-0900000000-d239dec0d0698dcf5911	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 50V, Positive-QTOF	splash10-002b-5900000000-f7c934b6a7ae66146cdc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Positive-QTOF	splash10-0002-0900000000-5a595ae4287dad4462ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-0b61359c01d65e58435c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 40V, Positive-QTOF	splash10-00kb-0900000000-3b45a2166157706a1cca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-777c533ba4aa455923a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 30V, Positive-QTOF	splash10-0002-2900000000-058ff3459772277358f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 10V, Positive-QTOF	splash10-0002-0900000000-c30749ad267ed24ed3ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxyquinoline 50V, Positive-QTOF	splash10-0002-3900000000-82e47a1ecd5ecda34bb6	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

62357

KEGG Compound ID

C06343

BioCyc ID

QUINOLIN-4-OL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15815

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1203921

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Hydroxyquinoline (HMDB0246466)

MOL for HMDB0246466 (4-Hydroxyquinoline)

3D MOL for HMDB0246466 (4-Hydroxyquinoline)

3D SDF for HMDB0246466 (4-Hydroxyquinoline)

3D-SDF for HMDB0246466 (4-Hydroxyquinoline)

PDB for HMDB0246466 (4-Hydroxyquinoline)

3D PDB for HMDB0246466 (4-Hydroxyquinoline)

SMILES for HMDB0246466 (4-Hydroxyquinoline)

INCHI for HMDB0246466 (4-Hydroxyquinoline)

Structure for HMDB0246466 (4-Hydroxyquinoline)

3D Structure for HMDB0246466 (4-Hydroxyquinoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra