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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 06:49:47 UTC
Update Date2021-09-14 15:20:04 UTC
HMDB IDHMDB0003892
Secondary Accession Numbers
  • HMDB03892
Metabolite Identification
Common Name(S)-N-Methylsalsolinol
Description(S)-N-Methylsalsolinol, also known as 1,2-ddtiq, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives (S)-N-Methylsalsolinol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make (S)-N-methylsalsolinol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (S)-N-Methylsalsolinol.
Structure
Data?1582752289
Synonyms
ValueSource
(R)-Isomer OF 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH
1,2-DDTIQMeSH
1,2-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH
HBR(R)-Isomer OF 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH
HBR(S)-Isomer OF 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH
N-Methyl-(S)-salsolinolHMDB
N-MethylsalsolinolHMDB
Chemical FormulaC11H15NO2
Average Molecular Weight193.2423
Monoisotopic Molecular Weight193.110278729
IUPAC Name(1S)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional NameN-methylsalsolinol
CAS Registry Number53622-85-8
SMILES
C[C@@H]1N(C)CCC2=CC(O)=C(O)C=C12
InChI Identifier
InChI=1S/C11H15NO2/c1-7-9-6-11(14)10(13)5-8(9)3-4-12(7)2/h5-7,13-14H,3-4H2,1-2H3/t7-/m0/s1
InChI KeyRKMGOUZXGHZLBJ-ZETCQYMHSA-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
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • 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
Disposition
ProcessNot Available
Role
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 Solubility21.9 g/LALOGPS
logP1.23ALOGPS
logP1.59ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)6.92ChemAxon
pKa (Strongest Basic)10.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.29 m³·mol⁻¹ChemAxon
Polarizability21.36 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]+144.89231661259
DarkChem[M-H]-142.38331661259
DeepCCS[M-2H]-177.07930932474
DeepCCS[M+Na]+151.9130932474
AllCCS[M+H]+143.232859911
AllCCS[M+H-H2O]+138.932859911
AllCCS[M+NH4]+147.132859911
AllCCS[M+Na]+148.332859911
AllCCS[M-H]-145.932859911
AllCCS[M+Na-2H]-146.432859911
AllCCS[M+HCOO]-147.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-N-MethylsalsolinolC[C@@H]1N(C)CCC2=CC(O)=C(O)C=C122770.1Standard polar33892256
(S)-N-MethylsalsolinolC[C@@H]1N(C)CCC2=CC(O)=C(O)C=C121747.2Standard non polar33892256
(S)-N-MethylsalsolinolC[C@@H]1N(C)CCC2=CC(O)=C(O)C=C121889.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-N-Methylsalsolinol,1TMS,isomer #1C[C@H]1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1C1841.7Semi standard non polar33892256
(S)-N-Methylsalsolinol,1TMS,isomer #2C[C@H]1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1C1831.1Semi standard non polar33892256
(S)-N-Methylsalsolinol,2TMS,isomer #1C[C@H]1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1C1860.0Semi standard non polar33892256
(S)-N-Methylsalsolinol,1TBDMS,isomer #1C[C@H]1C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1C2114.7Semi standard non polar33892256
(S)-N-Methylsalsolinol,1TBDMS,isomer #2C[C@H]1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CCN1C2108.1Semi standard non polar33892256
(S)-N-Methylsalsolinol,2TBDMS,isomer #1C[C@H]1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1C2338.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylsalsolinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-ce38275a97947ad0c2072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylsalsolinol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-2294000000-e81b4cd0f6a60cdbf2892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylsalsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylsalsolinol 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 - (S)-N-Methylsalsolinol 10V, Positive-QTOFsplash10-0006-0900000000-630f003fbd29862656db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 20V, Positive-QTOFsplash10-0006-0900000000-2332ab63301661d2ad8b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 40V, Positive-QTOFsplash10-007a-3900000000-829765b96f19c1734e8f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 10V, Negative-QTOFsplash10-0006-0900000000-550798399b578a198d462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 20V, Negative-QTOFsplash10-0006-0900000000-6c3f6aefc7671bf92e4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 40V, Negative-QTOFsplash10-05di-3900000000-8e1121f2eeab5ab9b4ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 10V, Negative-QTOFsplash10-0006-0900000000-5326ed117e0a68853a6c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 20V, Negative-QTOFsplash10-0006-0900000000-2db53ba347575442f27d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 40V, Negative-QTOFsplash10-001i-1900000000-79f2043772ff521702482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 10V, Positive-QTOFsplash10-0006-0900000000-093c204a145d72b06e8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 20V, Positive-QTOFsplash10-0006-0900000000-a5e47e491134faa38fe42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylsalsolinol 40V, Positive-QTOFsplash10-0ab9-5900000000-23e7e3619291802dc08d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.001 (0.002 - 0.006) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.001 (0.0054 - 0.011) uMAdult (>18 years old)Not SpecifiedParkinson's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0035 +/- 0.001 (0.002 - 0.005) uMAdult (>18 years old)Not SpecifiedMultiple System Atrophy (MSA) details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Naoi M, Maruyama W: Cell death of dopamine neurons in aging and Parkinson's disease. Mech Ageing Dev. 1999 Nov;111(2-3):175-88. [PubMed:10656535 ]
Multiple system atrophy
  1. Naoi M, Maruyama W: Cell death of dopamine neurons in aging and Parkinson's disease. Mech Ageing Dev. 1999 Nov;111(2-3):175-88. [PubMed:10656535 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023244
KNApSAcK IDNot Available
Chemspider ID110618
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124148
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE4890
MarkerDB IDMDB00000434
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Naoi M, Maruyama W: Cell death of dopamine neurons in aging and Parkinson's disease. Mech Ageing Dev. 1999 Nov;111(2-3):175-88. [PubMed:10656535 ]
  2. Takahashi T, Maruyama W, Deng Y, Dostert P, Nakahara D, Niwa T, Ohta S, Naoi M: Cytotoxicity of endogenous isoquinolines to human dopaminergic neuroblastoma SH-SY5Y cells. J Neural Transm (Vienna). 1997;104(1):59-66. [PubMed:9085193 ]
  3. Niwa T, Takeda N, Yoshizumi H, Tatematsu A, Yoshida M, Dostert P, Naoi M, Nagatsu T: Presence of 2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, novel endogenous amines, in parkinsonian and normal human brains. Biochem Biophys Res Commun. 1991 Jun 14;177(2):603-9. [PubMed:2049084 ]