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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

2013-05-09 21:16:15 UTC

Update Date

2023-02-21 17:29:50 UTC

HMDB ID

HMDB0060289

Secondary Accession Numbers

HMDB60289

Metabolite Identification

Common Name

Quinoline-4,8-diol

Description

Quinoline-4,8-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. Quinoline-4,8-diol is a strong basic compound (based on its pKa). Quinoline-4,8-diol exists in all living organisms, ranging from bacteria to humans. These are compounds containing a quinoline moiety bearing an hydroxyl group.

Structure

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

HEADER    PROTEIN                                 09-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    2    7    9                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3    9   12                                                  
CONECT    9    6    8   10                                                  
CONECT   10    5    9                                                       
CONECT   11    7                                                            
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
4,8-Dihydroxyquinoline	ChEBI

Chemical Formula

C₉H₇NO₂

Average Molecular Weight

161.1574

Monoisotopic Molecular Weight

161.047678473

IUPAC Name

quinoline-4,8-diol

Traditional Name

4,8-dihydroxyquinoline

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C(O)C=CN=C12

InChI Identifier

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

InChI Key

PYELIMVFIITPER-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
8-hydroxyquinoline
Dihydroquinoline
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyquinoline (CHEBI:28883 )

Ontology

Not Available

Feces (PMID: 27786174)

Source

Exogenous

Exogenous (HMDB: HMDB0060289)

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
Water Solubility	4.6 g/L	ALOGPS
logP	1.16	ALOGPS
logP	1.52	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	3.5	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	15.76 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]+	132.751	31661259
DarkChem	[M-H]-	129.521	31661259
DeepCCS	[M-2H]-	166.861	30932474
DeepCCS	[M+Na]+	142.286	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.5	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	130.6	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	2.33 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3276 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1229.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	378.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	229.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	467.3 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	409.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	665.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	766.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	91.7 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	1116.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	718.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	429.3 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	291.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinoline-4,8-diol	OC1=CC=CC2=C(O)C=CN=C12	2606.0	Standard polar	33892256
Quinoline-4,8-diol	OC1=CC=CC2=C(O)C=CN=C12	1703.1	Standard non polar	33892256
Quinoline-4,8-diol	OC1=CC=CC2=C(O)C=CN=C12	1776.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinoline-4,8-diol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C(O)C=CN=C12	1821.0	Semi standard non polar	33892256
Quinoline-4,8-diol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=NC2=C(O)C=CC=C12	1846.5	Semi standard non polar	33892256
Quinoline-4,8-diol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=NC2=C(O[Si](C)(C)C)C=CC=C12	1856.7	Semi standard non polar	33892256
Quinoline-4,8-diol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C(O)C=CN=C12	2079.3	Semi standard non polar	33892256
Quinoline-4,8-diol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=NC2=C(O)C=CC=C12	2121.0	Semi standard non polar	33892256
Quinoline-4,8-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=NC2=C(O[Si](C)(C)C(C)(C)C)C=CC=C12	2371.6	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 - Quinoline-4,8-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0900000000-871e0625a2410b46bae4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinoline-4,8-diol GC-MS (2 TMS) - 70eV, Positive	splash10-0g5c-4290000000-5a034fc41a9e9fd63975	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinoline-4,8-diol 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 - Quinoline-4,8-diol 10V, Positive-QTOF	splash10-03di-0900000000-11b0a2e1763d70b94d1a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinoline-4,8-diol 20V, Positive-QTOF	splash10-03di-0900000000-e80eda85b395a0f7f5be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinoline-4,8-diol 40V, Positive-QTOF	splash10-0f79-8900000000-0db241e9d8afb4d5e001	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinoline-4,8-diol 10V, Negative-QTOF	splash10-03di-0900000000-891b397c8a96d3908fde	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinoline-4,8-diol 20V, Negative-QTOF	splash10-03di-0900000000-42ec6eb81f54a0a8474a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinoline-4,8-diol 40V, Negative-QTOF	splash10-053r-0900000000-8178dc877217fa38cf3e	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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]-)	2023-02-04	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

Feces

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
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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05637

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440737

PDB ID

Not Available

ChEBI ID

28883

Food Biomarker Ontology

Not Available

VMH ID

48DHOXQUIN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

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

3-Hydroxykynurenamine + Oxygen → Quinoline-4,8-diol + Ammonia + Hydrogen peroxide	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

3-Hydroxykynurenamine + Oxygen → Quinoline-4,8-diol + Ammonia + Hydrogen peroxide	details

Showing metabocard for Quinoline-4,8-diol (HMDB0060289)

MOL for HMDB0060289 (Quinoline-4,8-diol)

3D MOL for HMDB0060289 (Quinoline-4,8-diol)

3D SDF for HMDB0060289 (Quinoline-4,8-diol)

3D-SDF for HMDB0060289 (Quinoline-4,8-diol)

PDB for HMDB0060289 (Quinoline-4,8-diol)

3D PDB for HMDB0060289 (Quinoline-4,8-diol)

SMILES for HMDB0060289 (Quinoline-4,8-diol)

INCHI for HMDB0060289 (Quinoline-4,8-diol)

Structure for HMDB0060289 (Quinoline-4,8-diol)

3D Structure for HMDB0060289 (Quinoline-4,8-diol)

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