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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-02 21:57:13 UTC
Update Date2022-09-22 18:34:32 UTC
HMDB IDHMDB0240311
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,8-Quinolinediol
Descriptionquinoline-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
Data?1591200226
Synonyms
ValueSource
2,8-DihydroxyquinolineChEBI
2,8-QuinolinediolChEBI
8-HydroxycarbostyrilChEBI
8-HydroxycarbostyrylChEBI
Quinolin-2,8-diolChEBI
2,8-DihydroxylquinolineHMDB
2,8-DHQHMDB
8-Hydroxy-1H-quinolin-2-oneHMDB
8-Hydroxy-2(1H)-quinolinoneHMDB
8-Hydroxy-2-oxo-1,2-dihydroquinolineHMDB
8-Hydroxyquinolin-2-oneHMDB
Chemical FormulaC9H7NO2
Average Molecular Weight161.16
Monoisotopic Molecular Weight161.047678469
IUPAC Name8-hydroxy-1,2-dihydroquinolin-2-one
Traditional Name8-hydroxyquinolin-2(1H)-one
CAS Registry Number15450-76-7
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 KeyZXZKYYHTWHJHFT-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentQuinolones 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.82ALOGPS
logP1.29ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.26 m³·mol⁻¹ChemAxon
Polarizability15.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+133.17630932474
DeepCCS[M-H]-130.33630932474
DeepCCS[M-2H]-166.51330932474
DeepCCS[M+Na]+141.90130932474
AllCCS[M+H]+132.532859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.932859911
AllCCS[M+Na]+138.232859911
AllCCS[M-H]-130.532859911
AllCCS[M+Na-2H]-131.032859911
AllCCS[M+HCOO]-131.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,8-QuinolinediolOC1=C2NC(=O)C=CC2=CC=C12823.4Standard polar33892256
2,8-QuinolinediolOC1=C2NC(=O)C=CC2=CC=C11823.2Standard non polar33892256
2,8-QuinolinediolOC1=C2NC(=O)C=CC2=CC=C11810.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,8-Quinolinediol,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C21785.1Semi standard non polar33892256
2,8-Quinolinediol,1TMS,isomer #2C[Si](C)(C)N1C(=O)C=CC2=CC=CC(O)=C211875.5Semi standard non polar33892256
2,8-Quinolinediol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C21965.2Semi standard non polar33892256
2,8-Quinolinediol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C22013.9Standard non polar33892256
2,8-Quinolinediol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C22052.8Standard polar33892256
2,8-Quinolinediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C22056.1Semi standard non polar33892256
2,8-Quinolinediol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)C=CC2=CC=CC(O)=C212074.1Semi standard non polar33892256
2,8-Quinolinediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C22354.9Semi standard non polar33892256
2,8-Quinolinediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C22427.3Standard non polar33892256
2,8-Quinolinediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C22304.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,8-Quinolinediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 35V, Positive-QTOFsplash10-03xu-0900000000-e5520ec4e5398fd057452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOFsplash10-03di-0900000000-ef018b38352e48dbe8c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Positive-QTOFsplash10-014i-2900000000-87afed2bc8d6b971414b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 0V, Positive-QTOFsplash10-03di-0900000000-0553cd1b88ef539e10c92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Positive-QTOFsplash10-014i-3900000000-a493b7655cae847ca9772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 35V, Negative-QTOFsplash10-03di-0900000000-a13dd1f921d203ee3c8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOFsplash10-03di-0900000000-9dbed49b41821c45f8162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 0V, Positive-QTOFsplash10-03di-0900000000-912279031aabba5fc2dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Negative-QTOFsplash10-03di-0900000000-7d4d08aceb1a4a8170bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Negative-QTOFsplash10-03di-0900000000-9517476b283b48123c052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Negative-QTOFsplash10-001i-5900000000-f0288a166a4d7a7038d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,8-Quinolinediol 30V, Negative-QTOFsplash10-08gi-1900000000-056394b3fdf51e2e573d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Positive-QTOFsplash10-03di-0900000000-d2b094746088a17847e12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Positive-QTOFsplash10-03di-0900000000-2a9bd7ec01c7c01d3b452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Positive-QTOFsplash10-001i-4900000000-d15dee9a896dd8ae965c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 10V, Negative-QTOFsplash10-03di-0900000000-29ea448bd0cee5fb98df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 20V, Negative-QTOFsplash10-03di-0900000000-d2ffdfabdb72be10c5362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-Quinolinediol 40V, Negative-QTOFsplash10-001i-1900000000-55b09d0fee173ed799532021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID87777
KEGG Compound IDC06342
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97250
PDB IDNot Available
ChEBI ID17715
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]