Human Metabolome Database Version 3.5

Showing metabocard for (R)-Salsolinol (HMDB05199)

Record Information
Version 3.5
Creation Date 2006-12-06 08:50:25 -0700
Update Date 2013-05-29 13:41:55 -0600
HMDB ID HMDB05199
Secondary Accession Numbers None
Metabolite Identification
Common Name (R)-Salsolinol
Description Salsolinol 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 Link_out).
Structure Thumb
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Synonyms
  1. (+)-(R)-Salsolinol
  2. (+)-Salsolinol
  3. (R)-(+)-Salsolinol
  4. (R)-Salsolinol
  5. 1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
Chemical Formula C10H13NO2
Average Molecular Weight 179.2157
Monoisotopic Molecular Weight 179.094628665
IUPAC Name 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional IUPAC Name 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
CAS Registry Number 525-72-4
SMILES CC1NCCC2=C1C=C(O)C(O)=C2
InChI Identifier InChI=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 Key IBRKLUSXDYATLG-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Isoquinolines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diphenol
  • Phenol
  • Phenol Derivative
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Isoquinolines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 6.71 g/L ALOGPS
LogP 0.16 ALOGPS
LogP 0.96 ChemAxon
LogS -1.43 ALOGPS
pKa (strongest acidic) 9.61 ChemAxon
pKa (strongest basic) 8.7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 52.49 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 51 ChemAxon
Polarizability 19.24 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0022 +/- 0.0015 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.00042 +/- 0.000094 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.005 +/- 0.002 uM Adult (>18 years old) Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0019 +/- 0.00078 uM Adult (>18 years old) Both After alcohol intake
Blood Detected and Quantified 0.0010 +/- 0.00043 uM Adult (>18 years old) Both Hypertension
Cerebrospinal Fluid (CSF) Detected and Quantified 0.005 +/- 0.001 uM Adult (>18 years old) Not Specified Parkinson's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.004 +/- 0.001 uM Adult (>18 years old) Not Specified Multiple System Atrophy (MSA)
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • Zhang W, Xie Y, Gu J, Ai S, Wang J, Yamamoto K, Jin L: Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. Analyst. 2004 Mar;129(3):229-34. Epub 2004 Feb 6. Pubmed: 14978525 Link_out
      Multiple system atrophy
      • 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 Link_out
          Hypertension
          • Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. Pubmed: 8255371 Link_out
              Associated OMIM IDs
              DrugBank ID Not Available
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB000429
              KNApSAcK ID Not Available
              Chemspider ID 49181 Link_out
              KEGG Compound ID C09642 Link_out
              BioCyc ID Not Available
              BiGG ID Not Available
              Wikipedia Link Not Available
              NuGOwiki Link HMDB05199 Link_out
              Metagene Link HMDB05199 Link_out
              METLIN ID Not Available
              PubChem Compound 54456 Link_out
              PDB ID Not Available
              ChEBI ID 123715 Link_out
              References
              Synthesis Reference Kovacs, Odon; Fodor, Gabor. The synthesis of tetrahydroisoquinoline alkaloids under physiological conditions. Chemische Berichte (1951), 84 795-801.
              Material Safety Data Sheet (MSDS) Not Available
              General References
              1. Zhang W, Xie Y, Gu J, Ai S, Wang J, Yamamoto K, Jin L: Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. Analyst. 2004 Mar;129(3):229-34. Epub 2004 Feb 6. Pubmed: 14978525 Link_out
              2. 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 Link_out
              3. Naoi M, Maruyama W, Nagy GM: Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains. Neurotoxicology. 2004 Jan;25(1-2):193-204. Pubmed: 14697894 Link_out