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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-04-02 21:57:13 UTC

Update Date

2022-09-22 18:34:32 UTC

HMDB ID

HMDB0240311

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,8-Quinolinediol

Description

quinoline-2,8-diol, also known as 2,8-quinolinediol or 8-hydroxycarbostyril, belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. Based on a literature review very few articles have been published on quinoline-2,8-diol.

Structure

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

HEADER    PROTEIN                                 03-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-20         0                                  
HETATM    1  O   UNK     0    8664.7188668.988   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.0438667.444   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.7168667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.3838666.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3828665.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.7168664.356   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8667.3788667.436   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8666.0458666.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0458665.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3788664.356   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.7128665.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.7128666.666   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    4    1    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    8   12                                                       
CONECT    8    9    7    3                                                  
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    2                                                  
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
2,8-Dihydroxyquinoline	ChEBI
2,8-Quinolinediol	ChEBI
8-Hydroxycarbostyril	ChEBI
8-Hydroxycarbostyryl	ChEBI
Quinolin-2,8-diol	ChEBI
2,8-Dihydroxylquinoline	HMDB
2,8-DHQ	HMDB
8-Hydroxy-1H-quinolin-2-one	HMDB
8-Hydroxy-2(1H)-quinolinone	HMDB
8-Hydroxy-2-oxo-1,2-dihydroquinoline	HMDB
8-Hydroxyquinolin-2-one	HMDB

Chemical Formula

C₉H₇NO₂

Average Molecular Weight

161.16

Monoisotopic Molecular Weight

161.047678469

IUPAC Name

8-hydroxy-1,2-dihydroquinolin-2-one

Traditional Name

8-hydroxyquinolin-2(1H)-one

CAS Registry Number

15450-76-7

SMILES

OC1=C2NC(=O)C=CC2=CC=C1

InChI Identifier

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

InChI Key

ZXZKYYHTWHJHFT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Quinolones and derivatives

Alternative Parents

Substituents

Quinolone
8-hydroxyquinoline
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Hydroxypyridine
Pyridine
Benzenoid
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolone (CHEBI:48988 )
monohydroxyquinoline (CHEBI:48988 )
a small molecule (QUINOLIN-28-DIOL )

Ontology

Not Available

Feces (PMID: 29808030)
Urine (PMID: 30089834)

Source

Exogenous

Exogenous (HMDB: HMDB0240311)

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	0.82	ALOGPS
logP	1.29	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.26 m³·mol⁻¹	ChemAxon
Polarizability	15.71 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
DeepCCS	[M+H]+	133.176	30932474
DeepCCS	[M-H]-	130.336	30932474
DeepCCS	[M-2H]-	166.513	30932474
DeepCCS	[M+Na]+	141.901	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.9	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	131.6	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.	3.67 minutes	32390414
Predicted by Siyang on May 30, 2022	10.293 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.68 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1081.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	208.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	377.4 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	353.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	660.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	344.7 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	1030.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	593.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	369.6 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	110.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,8-Quinolinediol	OC1=C2NC(=O)C=CC2=CC=C1	2823.4	Standard polar	33892256
2,8-Quinolinediol	OC1=C2NC(=O)C=CC2=CC=C1	1823.2	Standard non polar	33892256
2,8-Quinolinediol	OC1=C2NC(=O)C=CC2=CC=C1	1810.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,8-Quinolinediol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C2	1785.1	Semi standard non polar	33892256
2,8-Quinolinediol,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C=CC2=CC=CC(O)=C21	1875.5	Semi standard non polar	33892256
2,8-Quinolinediol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C2	1965.2	Semi standard non polar	33892256
2,8-Quinolinediol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C2	2013.9	Standard non polar	33892256
2,8-Quinolinediol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C2	2052.8	Standard polar	33892256
2,8-Quinolinediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C2	2056.1	Semi standard non polar	33892256
2,8-Quinolinediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C=CC2=CC=CC(O)=C21	2074.1	Semi standard non polar	33892256
2,8-Quinolinediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C2	2354.9	Semi standard non polar	33892256
2,8-Quinolinediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C2	2427.3	Standard non polar	33892256
2,8-Quinolinediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C2	2304.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-Quinolinediol 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 - 2,8-Quinolinediol 35V, Positive-QTOF	splash10-03xu-0900000000-e5520ec4e5398fd05745	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOF	splash10-03di-0900000000-ef018b38352e48dbe8c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Positive-QTOF	splash10-014i-2900000000-87afed2bc8d6b971414b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 0V, Positive-QTOF	splash10-03di-0900000000-0553cd1b88ef539e10c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Positive-QTOF	splash10-014i-3900000000-a493b7655cae847ca977	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 35V, Negative-QTOF	splash10-03di-0900000000-a13dd1f921d203ee3c8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOF	splash10-03di-0900000000-9dbed49b41821c45f816	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 0V, Positive-QTOF	splash10-03di-0900000000-912279031aabba5fc2dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Negative-QTOF	splash10-03di-0900000000-7d4d08aceb1a4a8170bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Negative-QTOF	splash10-03di-0900000000-9517476b283b48123c05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Negative-QTOF	splash10-001i-5900000000-f0288a166a4d7a7038d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Negative-QTOF	splash10-08gi-1900000000-056394b3fdf51e2e573d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOF	splash10-03di-0900000000-d2b094746088a17847e1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Positive-QTOF	splash10-03di-0900000000-2a9bd7ec01c7c01d3b45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Positive-QTOF	splash10-001i-4900000000-d15dee9a896dd8ae965c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Negative-QTOF	splash10-03di-0900000000-29ea448bd0cee5fb98df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Negative-QTOF	splash10-03di-0900000000-d2ffdfabdb72be10c536	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Negative-QTOF	splash10-001i-1900000000-55b09d0fee173ed79953	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	30089834	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	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

87777

KEGG Compound ID

C06342

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97250

PDB ID

Not Available

ChEBI ID

17715

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

Fan S, Yeon A, Shahid M, Anger JT, Eilber KS, Fiehn O, Kim J: Sex-associated differences in baseline urinary metabolites of healthy adults. Sci Rep. 2018 Aug 8;8(1):11883. doi: 10.1038/s41598-018-29592-3. [PubMed:30089834 ]

Showing metabocard for 2,8-Quinolinediol (HMDB0240311)

MOL for HMDB0240311 (2,8-Quinolinediol)

3D MOL for HMDB0240311 (2,8-Quinolinediol)

3D SDF for HMDB0240311 (2,8-Quinolinediol)

3D-SDF for HMDB0240311 (2,8-Quinolinediol)

PDB for HMDB0240311 (2,8-Quinolinediol)

3D PDB for HMDB0240311 (2,8-Quinolinediol)

SMILES for HMDB0240311 (2,8-Quinolinediol)

INCHI for HMDB0240311 (2,8-Quinolinediol)

Structure for HMDB0240311 (2,8-Quinolinediol)

3D Structure for HMDB0240311 (2,8-Quinolinediol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra