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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:54:31 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060335
Secondary Accession Numbers
  • HMDB60335
Metabolite Identification
Common Name1,2-Dihydronaphthalene-1,2-diol
Description1,2-Dihydronaphthalene-1,2-diol, also known as 1,2-dihydroxy-1,2-dihydronaphthalene or naphthalene-1,2-dihydrodiol, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1,2-Dihydronaphthalene-1,2-diol exists in all living organisms, ranging from bacteria to humans. 1,2-Dihydronaphthalene-1,2-diol 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 1,2-Dihydronaphthalene-1,2-diol.
Structure
Data?1563866046
Synonyms
ValueSource
1,2-Dihydroxy-1,2-dihydronaphthaleneChEBI
1,2-Dihydroxy-1,2-dihydronaphthalene, (cis)-(+-)-isomerHMDB
Naphthalene-1,2-dihydrodiolHMDB
trans-1,2-Dihydroxy-1,2-dihydronaphthaleneHMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (1S-trans)-isomerHMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (cis)-isomerHMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-isomerHMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-(+-)-isomerHMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-(-)-isomerHMDB
Chemical FormulaC10H10O2
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
IUPAC Name1,2-dihydronaphthalene-1,2-diol
Traditional Namenaphthalene-1,2-dihydrodiol
CAS Registry NumberNot Available
SMILES
OC1C=CC2=CC=CC=C2C1O
InChI Identifier
InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H
InChI KeyQPUHWUSUBHNZCG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
Water Solubility22.5 g/LALOGPS
logP0.63ALOGPS
logP1ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.38 m³·mol⁻¹ChemAxon
Polarizability16.84 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.23331661259
DarkChem[M-H]-130.01131661259
DeepCCS[M+H]+131.8130932474
DeepCCS[M-H]-129.15430932474
DeepCCS[M-2H]-165.71230932474
DeepCCS[M+Na]+140.88430932474
AllCCS[M+H]+136.932859911
AllCCS[M+H-H2O]+132.332859911
AllCCS[M+NH4]+141.232859911
AllCCS[M+Na]+142.432859911
AllCCS[M-H]-134.432859911
AllCCS[M+Na-2H]-135.032859911
AllCCS[M+HCOO]-135.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2-Dihydronaphthalene-1,2-diolOC1C=CC2=CC=CC=C2C1O2805.0Standard polar33892256
1,2-Dihydronaphthalene-1,2-diolOC1C=CC2=CC=CC=C2C1O1572.9Standard non polar33892256
1,2-Dihydronaphthalene-1,2-diolOC1C=CC2=CC=CC=C2C1O1597.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2-Dihydronaphthalene-1,2-diol,1TMS,isomer #1C[Si](C)(C)OC1C=CC2=CC=CC=C2C1O1615.5Semi standard non polar33892256
1,2-Dihydronaphthalene-1,2-diol,1TMS,isomer #2C[Si](C)(C)OC1C2=CC=CC=C2C=CC1O1587.8Semi standard non polar33892256
1,2-Dihydronaphthalene-1,2-diol,2TMS,isomer #1C[Si](C)(C)OC1C=CC2=CC=CC=C2C1O[Si](C)(C)C1621.1Semi standard non polar33892256
1,2-Dihydronaphthalene-1,2-diol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C=CC2=CC=CC=C2C1O1864.5Semi standard non polar33892256
1,2-Dihydronaphthalene-1,2-diol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C=CC1O1837.6Semi standard non polar33892256
1,2-Dihydronaphthalene-1,2-diol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C=CC2=CC=CC=C2C1O[Si](C)(C)C(C)(C)C2097.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fsi-0900000000-30816753a4b47bb8c7ca2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-7390000000-d91f46a72c7b1bdbc6522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 10V, Positive-QTOFsplash10-03di-0900000000-1d76de306a4e3266c7122017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 20V, Positive-QTOFsplash10-03e9-0900000000-d41bfc0f04e29afcef502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 40V, Positive-QTOFsplash10-0f6x-9500000000-e72884c251ba662054922017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 10V, Negative-QTOFsplash10-03di-0900000000-b294d622ce5e72f2bc992017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 20V, Negative-QTOFsplash10-03di-0900000000-368dc2351487ced1da902017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 40V, Negative-QTOFsplash10-0w4l-1900000000-f0e470bae4e9547548012017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID355
KEGG Compound IDC06205
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound362
PDB IDNot Available
ChEBI ID28516
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
1,2-Dihydronaphthalene-1,2-diol + NADP → Naphthalene-1,2-diol + NADPH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:
EPHX1
Uniprot ID:
P07099
Molecular weight:
52948.48
Reactions
Naphthalene epoxide + Water → 1,2-Dihydronaphthalene-1,2-dioldetails
(1S,2R)-Naphthalene 1,2-oxide + Water → 1,2-Dihydronaphthalene-1,2-dioldetails