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Showing Compound Salsolinol (FDB000429)

Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2019-11-26 02:54:46 UTC
Primary IDFDB000429
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSalsolinol
DescriptionSalsolinol is an endogenous catechol isoquinoline detected in humans. Salsolinol was detected in urine of parkinsonian patients administered with L-DOPA. This finding stimulated the studies on Salsolinol derivatives in the brain, and gave new aspects of the endogenous alkaloids, which had been considered to occur only in plants. In normal non-alcoholic subjects and alcoholics, Salsolinol and O-methylated Salsolinol were found in urine, cerebrospinal fluid and brains. Salsolinol has an asymmetric center at first position and exists as (R)- and (S)enantiomer. The (R)enantiomer of Salsolinol is predominant in urine from healthy volunteers. Only the (R)enantiomers of Salsolinol and N-methylated Salsolinol occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S)enantiomers were not detected. (R)salsolinol synthase catalyzes the enantio-selective synthesis of (R)Salsolinol and 1-carboxyl(R)Salsolinol from dopamine with acetaldehyde or pyruvic acid. The N-methylation of (R)salsolinol into N-methylsalsolinol (NMSal) is catalyzed by two N-methyltransferases with different optimum pH, at pH 7.0 and 8.4. NM(R)Salsolinol is enzymatically oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion (DMDHIQ+) by an oxidase sensitive to semicarbaside and also non-enzymatically by autoxidation. NM(R)Salsolinol and its precursor, dopamine, were found to occur selectively in the nigro-striatum, whereas (R)Salsolinol distributes uniformly among the brain regions. (PMID 14697894) [HMDB].
CAS Number525-72-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-(R)-SalsolinolHMDB
(+)-SalsolinolHMDB
(R)-(+)-SalsolinolHMDB
1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineHMDB
Salsolinol, (S)-isomerHMDB
1-Methyl-6,7-dihydroxytetrahydroisoquinolineHMDB
Salsolinol hydrobromideHMDB
SalsolinolHMDB
Salsolinol, (+-)-isomerHMDB
(R)-SalsolinolHMDB
1,2,3,4-Tetrahydro-1-methyl-6,7-isoquinolinediol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility6.71 g/LALOGPS
logP0.16ALOGPS
logP0.96ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)8.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51 m³·mol⁻¹ChemAxon
Polarizability19.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13NO2
IUPAC name1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
InChI IdentifierInChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3
InChI KeyIBRKLUSXDYATLG-UHFFFAOYSA-N
Isomeric SMILESCC1NCCC2=C1C=C(O)C(O)=C2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
Classification
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 effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.02%; H 7.31%; N 7.82%; O 17.85%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSalsolinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ik9-0900000000-ea926c78d9164b4155dfSpectrum
Predicted GC-MSSalsolinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-3295000000-9789c284ef49e7af9bffSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01q9-0900000000-2c29348adb1dba658757Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ot-0900000000-a28325af4d693ae8c614Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-d89b4eb37f9694e3dbb2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-fd496b1ca2ec080ac77bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-2894c6730bbdd8586e0dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-b95a812b67613811248bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-e65251ff89ea89a15814Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-ce7a81f09123f28c4b24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1c070d491bdf6a8f80d3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-7a8e025141a2d1299eb4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06y9-3900000000-bed1ede28e58e633dcbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f913db2f113ff2f73d08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-726420a5901821528a90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-5900000000-aaac23c6385c30ec14b5Spectrum
NMRNot Available
ChemSpider ID49181
ChEMBL IDCHEMBL416732
KEGG Compound IDC09642
Pubchem Compound ID54456
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05199
CRC / DFC (Dictionary of Food Compounds) IDBCB20-H:BCB20-H
EAFUS IDNot Available
Dr. Duke IDSALSOLINOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cardiac38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
hypertensiveDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).