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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 21:04:35 UTC
Update Date2023-02-21 17:17:14 UTC
HMDB IDHMDB0006044
Secondary Accession Numbers
  • HMDB06044
Metabolite Identification
Common NameNorsalsolinol
DescriptionNorsalsolinol is a putative metabolic neuromodulators that hs been found to be present in both rat and human brains. It modulates dopaminergic transmission and have been shown to be associated with neurotoxicity within cells and diseases such as alcoholism and Parkinsonism. Norsalsolinol can be synthesized in vivo non-enzymatically by condensation of dopamine with formaldehyde, the oxidized metabolite of methanol.
Structure
Data?1676999834
Synonyms
ValueSource
Norsalsolinol hydrobromideMeSH
Norsalsolinol hydrochlorideMeSH
Norsalsolinol, 3H-labeled CPDMeSH
1,2,3,4-tetrahydro-6,7-IsoquinolinediolHMDB
6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinolineHMDB
6,7-DihydroxytetrahydroisoquinolineHMDB
tetrahydro-6,7-IsoquinolinediolHMDB
NorsalsolinolMeSH
Chemical FormulaC9H11NO2
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
IUPAC Name1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional Namenorsalsolinol
CAS Registry Number34827-33-3
SMILES
OC1=C(O)C=C2CNCCC2=C1
InChI Identifier
InChI=1S/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2
InChI KeyMBFUSGLXKQWVDW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility12 g/LALOGPS
logP-0.13ALOGPS
logP0.58ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.58 m³·mol⁻¹ChemAxon
Polarizability17.28 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]+133.40431661259
DarkChem[M-H]-130.22431661259
DeepCCS[M+H]+137.74630932474
DeepCCS[M-H]-134.44830932474
DeepCCS[M-2H]-171.41430932474
DeepCCS[M+Na]+146.95230932474
AllCCS[M+H]+135.332859911
AllCCS[M+H-H2O]+130.832859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-135.332859911
AllCCS[M+Na-2H]-136.032859911
AllCCS[M+HCOO]-136.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorsalsolinolOC1=C(O)C=C2CNCCC2=C12368.2Standard polar33892256
NorsalsolinolOC1=C(O)C=C2CNCCC2=C11770.2Standard non polar33892256
NorsalsolinolOC1=C(O)C=C2CNCCC2=C11886.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norsalsolinol,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O)CNCC21832.8Semi standard non polar33892256
Norsalsolinol,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)CCNC21832.9Semi standard non polar33892256
Norsalsolinol,1TMS,isomer #3C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C11973.5Semi standard non polar33892256
Norsalsolinol,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CNCC21866.0Semi standard non polar33892256
Norsalsolinol,2TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)CN([Si](C)(C)C)CC21886.7Semi standard non polar33892256
Norsalsolinol,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)C21874.7Semi standard non polar33892256
Norsalsolinol,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC21932.9Semi standard non polar33892256
Norsalsolinol,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC21967.8Standard non polar33892256
Norsalsolinol,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC22062.4Standard polar33892256
Norsalsolinol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CNCC22114.0Semi standard non polar33892256
Norsalsolinol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCNC22107.6Semi standard non polar33892256
Norsalsolinol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C12178.6Semi standard non polar33892256
Norsalsolinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CNCC22347.8Semi standard non polar33892256
Norsalsolinol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CN([Si](C)(C)C(C)(C)C)CC22371.9Semi standard non polar33892256
Norsalsolinol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)C22373.2Semi standard non polar33892256
Norsalsolinol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC22630.0Semi standard non polar33892256
Norsalsolinol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC22657.5Standard non polar33892256
Norsalsolinol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC22465.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norsalsolinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bi-1900000000-679885412288d3a64d3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norsalsolinol GC-MS (2 TMS) - 70eV, Positivesplash10-00du-3190000000-6081caf19417015960d42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norsalsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norsalsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 10V, Positive-QTOFsplash10-014i-0900000000-6a97378ae1f9b27d97f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 20V, Positive-QTOFsplash10-014r-0900000000-2e841407c0716ade36d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 40V, Positive-QTOFsplash10-106v-7900000000-825205ecfbbbc20670c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 10V, Negative-QTOFsplash10-03di-0900000000-9ebff04bba1dd29e170f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 20V, Negative-QTOFsplash10-03di-0900000000-c11ff999c02984e87d5f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 40V, Negative-QTOFsplash10-0a4m-4900000000-e08e2858281b324fde482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 10V, Negative-QTOFsplash10-03di-0900000000-58730e09c186a15c21ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 20V, Negative-QTOFsplash10-03di-0900000000-08447749b14e173ff1022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 40V, Negative-QTOFsplash10-0006-9700000000-5d6e4fb1e2ebc89ffec32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 10V, Positive-QTOFsplash10-014i-0900000000-ec6dcf9afb4af34cdf102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 20V, Positive-QTOFsplash10-014i-0900000000-6e01e6a1fb7a92704dd82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsalsolinol 40V, Positive-QTOFsplash10-00kf-9600000000-8c87667ad0decf4c37472021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 IDFDB023817
KNApSAcK IDNot Available
Chemspider ID33891
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorsalsolinol
METLIN IDNot Available
PubChem Compound36937
PDB IDNot Available
ChEBI ID110006
Food Biomarker OntologyNot Available
VMH IDCE2172
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available