MiMeDB: Showing metabocard for (R)-Salsolinol (MMDBc0000436)

Plant

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:43 UTC

Update Date

2024-10-09 19:56:12 UTC

Metabolite ID

MMDBc0000436

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3,4-Tetrahydro-1-methyl-6,7-isoquinolinediol	ChEBI
1,2,3,4-Tetrahydro-1-methylisoquinoline-6,7-diol	ChEBI
1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	ChEBI
1-Methyl-6,7-dihydroxytetrahydroisoquinoline	ChEBI

Molecular Formula

C₁₀H₁₃NO₂

Average Mass

179.2157

Monoisotopic Mass

179.094628665

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	268.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	194.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	50.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	230.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	268.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	253.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	456.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	649.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	370.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	139.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	489.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	149.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	80.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	267.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	572.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	37.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	174.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	635.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	577.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(R)-Salsolinol_TMS_1	CC1NCCC2=CC(O)=C(O[Si](C)(C)C)C=C21	standard non polar	2025-10-23	1816.12
Gas Chromatography	(R)-Salsolinol_TMS_2	CC1NCCC2=CC(O[Si](C)(C)C)=C(O)C=C21	standard non polar	2025-10-23	1843.44
Gas Chromatography	(R)-Salsolinol_TMS_3	CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C	standard non polar	2025-10-23	1888.38
Gas Chromatography	(R)-Salsolinol_TMS_4	CC1NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	standard non polar	2025-10-23	1790.25
Gas Chromatography	(R)-Salsolinol_TMS_5	CC1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C	standard non polar	2025-10-23	1765.97
Gas Chromatography	(R)-Salsolinol_TMS_6	CC1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	standard non polar	2025-10-23	1780.94
Gas Chromatography	(R)-Salsolinol_TMS_7	CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	standard non polar	2025-10-23	1782.88
Gas Chromatography	(R)-Salsolinol_TMS_1	CC1NCCC2=CC(O)=C(O[Si](C)(C)C)C=C21	standard polar	2025-10-23	2111.36
Gas Chromatography	(R)-Salsolinol_TMS_2	CC1NCCC2=CC(O[Si](C)(C)C)=C(O)C=C21	standard polar	2025-10-23	2005.89
Gas Chromatography	(R)-Salsolinol_TMS_3	CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C	standard polar	2025-10-23	1744.15
Gas Chromatography	(R)-Salsolinol_TMS_4	CC1NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	standard polar	2025-10-23	2344.85
Gas Chromatography	(R)-Salsolinol_TMS_5	CC1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C	standard polar	2025-10-23	2517.34
Gas Chromatography	(R)-Salsolinol_TMS_6	CC1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	standard polar	2025-10-23	1693.81
Gas Chromatography	(R)-Salsolinol_TMS_7	CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	standard polar	2025-10-23	1922.19

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Hypertension	Association	Human Blood	HMDB	8255371
Multiple system atrophy	Association	Human Cerebrospinal Fluid (CSF)	HMDB	10656535
Parkinson's disease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	14978525

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	1	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human feces; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0010	0.00043	uM	Adult (>18 years old)	Both	Hypertension	HMDB	8255371
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.004	0.001	uM	Adult (>18 years old)	Not Specified	Multiple System Atrophy (MSA)	HMDB	10656535
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.005	0.001	uM	Adult (>18 years old)	Not Specified	Parkinson's disease	HMDB	14978525
Human Blood	Detected and Quantified	0.00042	0.000094	uM	Adult (>18 years old)	Both	Normal	HMDB	8255371
Human Blood	Detected and Quantified	0.0022	0.0015	uM	Adult (>18 years old)	Both	Normal	HMDB	8651468
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.005	0.002	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	14978525
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

194221

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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. doi: 10.1016/s0047-6374(99)00064-0. [PubMed:10656535 ]
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. doi: 10.1016/S0161-813X(03)00099-8. [PubMed:14697894 ]
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. doi: 10.1039/b314277a. Epub 2004 Feb 6. [PubMed:14978525 ]

Showing metabocard for (R)-Salsolinol (MMDBc0000436)

MOL for #<Metabolite:0x00007f9aad228f40>

3D MOL for #<Metabolite:0x00007f9aad228f40>

3D SDF for #<Metabolite:0x00007f9aad228f40>

3D-SDF for #<Metabolite:0x00007f9aad228f40>

PDB for #<Metabolite:0x00007f9aad228f40>

3D PDB for #<Metabolite:0x00007f9aad228f40>

SMILES for #<Metabolite:0x00007f9aad228f40>

INCHI for #<Metabolite:0x00007f9aad228f40>

Structure for #<Metabolite:0x00007f9aad228f40>

3D Structure for #<Metabolite:0x00007f9aad228f40>