Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2019-11-26 02:54:47 UTC
Primary IDFDB000430
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Salsolinol
Description(r)-salsolinol, also known as salsolinol, (+-)-isomer or 1-methyl-6,7-dihydroxytetrahydroisoquinoline, is a member of the class of compounds known as tetrahydroisoquinolines. Tetrahydroisoquinolines are tetrahydrogenated isoquinoline derivatives (r)-salsolinol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (r)-salsolinol can be found in cocoa and cocoa products and fruits, which makes (r)-salsolinol a potential biomarker for the consumption of these food products (r)-salsolinol can be found primarily in blood, cerebrospinal fluid (CSF), and feces. Moreover, (r)-salsolinol is found to be associated with hypertension, multiple system atrophy, and parkinson's disease.
CAS Number27740-96-1
Structure
Thumb
Synonyms
SynonymSource
(-)-SalsolinolHMDB
1,2,3,4-tetrahydro-1-Methyl-(S)-6,7-isoquinolinediolHMDB
Salsolinol, (S)-isomerMeSH, HMDB
Salsolinol hydrobromideMeSH, HMDB
Salsolinol, (+-)-isomerMeSH, HMDB
1-Methyl-6,7-dihydroxytetrahydroisoquinolineMeSH, HMDB
SalsolinolKEGG
(S)-1,2,3,4-Tetrahydro-1-methyl-6,7-isoquinolinediolbiospider
6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-methyl-, (S)-biospider
Predicted Properties
PropertyValueSource
Water Solubility6.71 g/LALOGPS
logP0.16ALOGPS
logP1.07ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)8.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51 m³·mol⁻¹ChemAxon
Polarizability19.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13NO2
IUPAC name(1S)-1-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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.02%; H 7.31%; N 7.82%; O 17.85%DFC
Melting PointMp 174-175° (hydrobromide)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -30.9 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ik9-0900000000-9218e2559691129a8d6eSpectrum
Predicted GC-MS, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-3394000000-d3f7f4ba883d5f5bdabcSpectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-e8a258462f9b922c3bf7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03ea-0900000000-bbaa7aafe08efa5dc301Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kb-0900000000-6e9f53c92f9b3f912744Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01q9-0900000000-f9be5378031284412ee4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-3a69d1707ac128ff83cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-b3f3459ae2e284d826a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06y9-3900000000-475a6d103e86d53fde2eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f913db2f113ff2f73d08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-3977a8d4ae142f8ac0c9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-6900000000-4ed53d992ff5b6e70668Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-e9e4d0ba83478e578c42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-93f4e0138ab7fe5d7041Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ef6ae59e91e658cf298aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-6326446584297a254a6aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-5d789e6d48fe029761d8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069c-7900000000-591a354d439d1c22c60cSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09642
Pubchem Compound ID91588
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBCB20-H:BCB23-K
EAFUS IDNot Available
Dr. Duke ID(-)-SALSOLINOL
BIGG IDNot Available
KNApSAcK IDC00001915
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
dopamine blocker48560 A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.DUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.