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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 10:23:06 UTC

Update Date

2023-02-21 17:16:54 UTC

HMDB ID

HMDB0004077

Secondary Accession Numbers

HMDB04077

Metabolite Identification

Common Name

4,6-Dihydroxyquinoline

Description

4,6-Dihydroxyquinoline, also known as quinoline-4,6-diol, belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. 4,6-Dihydroxyquinoline exists in all living organisms, ranging from bacteria to humans. In humans, 4,6-dihydroxyquinoline is involved in the tryptophan metabolism pathway. 4,6-Dihydroxyquinoline 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 4,6-dihydroxyquinoline a potential biomarker for the consumption of these foods. 4,6-Dihydroxyquinoline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4,6-Dihydroxyquinoline.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      24.334 -18.916   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.334 -20.456   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.668 -21.226   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.002 -20.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.002 -18.916   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      25.668 -18.146   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      28.335 -21.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.669 -20.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.669 -18.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.335 -18.146   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      25.668 -22.766   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      31.003 -21.226   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    3                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-1H-quinolin-4-one	ChEBI
Quinoline-4,6-diol	Kegg
4,6-Quinolinediol	HMDB

Chemical Formula

C₉H₇NO₂

Average Molecular Weight

161.1574

Monoisotopic Molecular Weight

161.047678473

IUPAC Name

quinoline-4,6-diol

Traditional Name

4,6-dihydroxyquinoline

CAS Registry Number

3517-61-1

SMILES

OC1=CC2=C(O)C=CN=C2C=C1

InChI Identifier

InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)

InChI Key

XFALURCRIGINGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroxyquinolones

Alternative Parents

Substituents

Hydroxyquinolone
Dihydroquinolone
Hydroxyquinoline
Dihydroquinoline
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyquinoline (CHEBI:28799 )

Ontology

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	3.96 g/L	ALOGPS
logP	1.09	ALOGPS
logP	1.52	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	2.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.94 m³·mol⁻¹	ChemAxon
Polarizability	15.8 Å³	ChemAxon
Number of Rings	2	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]+	133.918	31661259
DarkChem	[M-H]-	131.827	31661259
DeepCCS	[M+H]+	131.693	30932474
DeepCCS	[M-H]-	128.943	30932474
DeepCCS	[M-2H]-	165.1	30932474
DeepCCS	[M+Na]+	140.497	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	137.0	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	131.8	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.	2.86 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3399 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.38 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	105.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1124.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	340.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	75.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	339.3 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	262.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	751.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	664.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.0 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	922.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	800.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	511.4 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	262.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,6-Dihydroxyquinoline	OC1=CC2=C(O)C=CN=C2C=C1	2876.0	Standard polar	33892256
4,6-Dihydroxyquinoline	OC1=CC2=C(O)C=CN=C2C=C1	1898.8	Standard non polar	33892256
4,6-Dihydroxyquinoline	OC1=CC2=C(O)C=CN=C2C=C1	1936.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,6-Dihydroxyquinoline,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2N=CC=C(O)C2=C1	1869.4	Semi standard non polar	33892256
4,6-Dihydroxyquinoline,1TMS,isomer #2	C[Si](C)(C)OC1=CC=NC2=CC=C(O)C=C12	1843.5	Semi standard non polar	33892256
4,6-Dihydroxyquinoline,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2N=CC=C(O[Si](C)(C)C)C2=C1	1884.3	Semi standard non polar	33892256
4,6-Dihydroxyquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2N=CC=C(O)C2=C1	2121.8	Semi standard non polar	33892256
4,6-Dihydroxyquinoline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=NC2=CC=C(O)C=C12	2115.3	Semi standard non polar	33892256
4,6-Dihydroxyquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2N=CC=C(O[Si](C)(C)C(C)(C)C)C2=C1	2417.1	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 - 4,6-Dihydroxyquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0900000000-5a26ca29602b82b947ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,6-Dihydroxyquinoline GC-MS (2 TMS) - 70eV, Positive	splash10-00ec-4190000000-4bb8d953c5850dd96f48	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,6-Dihydroxyquinoline 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 - 4,6-Dihydroxyquinoline 10V, Positive-QTOF	splash10-03di-0900000000-2b4e8673d9953857188d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Positive-QTOF	splash10-03di-0900000000-664352c4cf4241c0a1c4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Positive-QTOF	splash10-053r-2900000000-05e37aff72635356f2cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Negative-QTOF	splash10-03di-0900000000-34a29a4deafcb0ad7c33	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Negative-QTOF	splash10-03di-0900000000-06fb975c74de0f90f723	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Negative-QTOF	splash10-053r-0900000000-39deb8142073ba5b68ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Positive-QTOF	splash10-03di-0900000000-d2b094746088a17847e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Positive-QTOF	splash10-03di-0900000000-d9bf4aaec04c4b90185a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Positive-QTOF	splash10-0159-4900000000-d7445a5c12b24666d75a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Negative-QTOF	splash10-03di-0900000000-29ea448bd0cee5fb98df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Negative-QTOF	splash10-03di-0900000000-02e9863a91ed972b84eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Negative-QTOF	splash10-053r-5900000000-f7f1ae1acee5ecfdcc35	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

46176

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440738

PDB ID

Not Available

ChEBI ID

28799

Food Biomarker Ontology

Not Available

VMH ID

46DHOXQUIN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Noguchi, Tomoo; Kaseda, Hiroki; Kido, Ryo; Matsumura, Yuichi. 5-Hydroxykynurenine decarboxylase in rat intestine. Journal of Biochemistry (Tokyo, Japan) (1970), 67(1), 113-21.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Water	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Water	details

Showing metabocard for 4,6-Dihydroxyquinoline (HMDB0004077)

MOL for HMDB0004077 (4,6-Dihydroxyquinoline)

3D MOL for HMDB0004077 (4,6-Dihydroxyquinoline)

3D SDF for HMDB0004077 (4,6-Dihydroxyquinoline)

3D-SDF for HMDB0004077 (4,6-Dihydroxyquinoline)

PDB for HMDB0004077 (4,6-Dihydroxyquinoline)

3D PDB for HMDB0004077 (4,6-Dihydroxyquinoline)

SMILES for HMDB0004077 (4,6-Dihydroxyquinoline)

INCHI for HMDB0004077 (4,6-Dihydroxyquinoline)

Structure for HMDB0004077 (4,6-Dihydroxyquinoline)

3D Structure for HMDB0004077 (4,6-Dihydroxyquinoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions