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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-12-06 15:50:25 UTC

Update Date

2023-02-21 17:17:07 UTC

HMDB ID

HMDB0005199

Secondary Accession Numbers

HMDB05199

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.130 -15.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.797 -14.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.797 -12.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.130 -12.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.464 -12.898   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.464 -14.438   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.463 -15.207   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      24.463 -12.128   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      29.798 -15.207   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      31.131 -14.438   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      31.131 -12.898   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.798 -12.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.798 -16.747   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    1    9                                                  
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    6   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-(R)-Salsolinol	HMDB
(+)-Salsolinol	HMDB
(R)-(+)-Salsolinol	HMDB
1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	HMDB
Salsolinol, (S)-isomer	HMDB
1-Methyl-6,7-dihydroxytetrahydroisoquinoline	HMDB
Salsolinol hydrobromide	HMDB
Salsolinol	HMDB
Salsolinol, (+-)-isomer	HMDB

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 Name

(+)-salsolinol

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

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Multiple system atrophy (HMDB: HMDB0005199)

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0005199)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0005199)
Cerebrospinal fluid (HMDB: HMDB0005199)
Cerebrospinal Fluid (CSF) (PMID: 14978525)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0005199)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005199)

Source

Endogenous

Endogenous (HMDB: HMDB0005199)

Plant

Plant (HMDB: HMDB0005199)
Theobroma cacao (HMDB: HMDB0005199)

Exogenous

Food

Food (HMDB: HMDB0005199)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Fruit

Tropical fruit

Custard apple (FooDB: FOOD00014)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Biological role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.71 g/L	ALOGPS
logP	0.16	ALOGPS
logP	0.96	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	8.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51 m³·mol⁻¹	ChemAxon
Polarizability	19.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.834	31661259
DarkChem	[M-H]-	137.922	31661259
DeepCCS	[M+H]+	139.506	30932474
DeepCCS	[M-H]-	135.678	30932474
DeepCCS	[M-2H]-	173.195	30932474
DeepCCS	[M+Na]+	148.734	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.7	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	140.3	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Salsolinol	CC1NCCC2=C1C=C(O)C(O)=C2	2574.3	Standard polar	33892256
(R)-Salsolinol	CC1NCCC2=C1C=C(O)C(O)=C2	1791.6	Standard non polar	33892256
(R)-Salsolinol	CC1NCCC2=C1C=C(O)C(O)=C2	1907.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Salsolinol,1TMS,isomer #1	CC1NCCC2=CC(O)=C(O[Si](C)(C)C)C=C21	1878.8	Semi standard non polar	33892256
(R)-Salsolinol,1TMS,isomer #2	CC1NCCC2=CC(O[Si](C)(C)C)=C(O)C=C21	1873.4	Semi standard non polar	33892256
(R)-Salsolinol,1TMS,isomer #3	CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C	1993.4	Semi standard non polar	33892256
(R)-Salsolinol,2TMS,isomer #1	CC1NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	1905.1	Semi standard non polar	33892256
(R)-Salsolinol,2TMS,isomer #2	CC1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C	1917.5	Semi standard non polar	33892256
(R)-Salsolinol,2TMS,isomer #3	CC1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	1921.9	Semi standard non polar	33892256
(R)-Salsolinol,3TMS,isomer #1	CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	1990.3	Semi standard non polar	33892256
(R)-Salsolinol,3TMS,isomer #1	CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	1967.4	Standard non polar	33892256
(R)-Salsolinol,3TMS,isomer #1	CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C	2053.2	Standard polar	33892256
(R)-Salsolinol,1TBDMS,isomer #1	CC1NCCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C21	2131.8	Semi standard non polar	33892256
(R)-Salsolinol,1TBDMS,isomer #2	CC1NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C21	2131.9	Semi standard non polar	33892256
(R)-Salsolinol,1TBDMS,isomer #3	CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C	2215.9	Semi standard non polar	33892256
(R)-Salsolinol,2TBDMS,isomer #1	CC1NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	2375.0	Semi standard non polar	33892256
(R)-Salsolinol,2TBDMS,isomer #2	CC1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C	2426.8	Semi standard non polar	33892256
(R)-Salsolinol,2TBDMS,isomer #3	CC1C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	2420.0	Semi standard non polar	33892256
(R)-Salsolinol,3TBDMS,isomer #1	CC1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	2674.2	Semi standard non polar	33892256
(R)-Salsolinol,3TBDMS,isomer #1	CC1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	2659.2	Standard non polar	33892256
(R)-Salsolinol,3TBDMS,isomer #1	CC1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C	2463.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Salsolinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ik9-0900000000-ea926c78d9164b4155df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Salsolinol GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-3295000000-9789c284ef49e7af9bff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Salsolinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOF	splash10-01q9-0900000000-2c29348adb1dba658757	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOF	splash10-01ot-0900000000-a28325af4d693ae8c614	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOF	splash10-00kb-0900000000-d89b4eb37f9694e3dbb2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOF	splash10-014i-0900000000-fd496b1ca2ec080ac77b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOF	splash10-03di-0900000000-2894c6730bbdd8586e0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOF	splash10-03di-0900000000-b95a812b67613811248b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOF	splash10-03di-0900000000-e65251ff89ea89a15814	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOF	splash10-03di-0900000000-ce7a81f09123f28c4b24	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOF	splash10-01ot-0900000000-2e943291c5430f91a8ff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOF	splash10-00kb-0900000000-b73360d52cf5dff31b8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOF	splash10-01q9-0900000000-2821f1026dd4b464da9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOF	splash10-01ot-0900000000-39e018ed344d997de3b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 30V, Positive-QTOF	splash10-014i-0900000000-9e8d0f4134ccc42a8296	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOF	splash10-00kb-0900000000-b99cb041281370993301	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOF	splash10-01q9-0900000000-5cd66c681b07ac5f232e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOF	splash10-01ot-0900000000-24e6da15427270ddc80c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 70V, Positive-QTOF	splash10-03di-0900000000-3755faa761a6e281bf8b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 55V, Positive-QTOF	splash10-03di-0900000000-be13089127e47b801b60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOF	splash10-00kb-0900000000-d45c2139d9620f895f41	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOF	splash10-001i-0900000000-1c070d491bdf6a8f80d3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOF	splash10-001i-0900000000-7a8e025141a2d1299eb4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 40V, Positive-QTOF	splash10-06y9-3900000000-bed1ede28e58e633dcbe	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 10V, Negative-QTOF	splash10-004i-0900000000-f913db2f113ff2f73d08	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 20V, Negative-QTOF	splash10-004i-0900000000-726420a5901821528a90	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Salsolinol 40V, Negative-QTOF	splash10-03dl-5900000000-aaac23c6385c30ec14b5	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0022 +/- 0.0015 uM	Adult (>18 years old)	Both	Normal	8651468	details
Blood	Detected and Quantified	0.00042 +/- 0.000094 uM	Adult (>18 years old)	Both	Normal	8255371	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 +/- 0.002 uM	Adult (>18 years old)	Not Specified	Normal	14978525	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0019 +/- 0.00078 uM	Adult (>18 years old)	Both	After alcohol intake	8651468	details
Blood	Detected and Quantified	0.0010 +/- 0.00043 uM	Adult (>18 years old)	Both	Hypertension	8255371	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 +/- 0.001 uM	Adult (>18 years old)	Not Specified	Parkinson's disease	14978525	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.004 +/- 0.001 uM	Adult (>18 years old)	Not Specified	Multiple System Atrophy (MSA)	10656535	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

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 ]
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 ]
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 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

145500 (Hypertension)
168600 (Parkinson's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018047

KNApSAcK ID

Not Available

Chemspider ID

49181

KEGG Compound ID

C09642

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54456

PDB ID

Not Available

ChEBI ID

123715

Food Biomarker Ontology

Not Available

VMH ID

C09642

MarkerDB ID

Not Available

Good Scents ID

Not Available

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

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 ]
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 ]
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 ]

Showing metabocard for (R)-Salsolinol (HMDB0005199)

MOL for HMDB0005199 ((R)-Salsolinol)

3D MOL for HMDB0005199 ((R)-Salsolinol)

3D SDF for HMDB0005199 ((R)-Salsolinol)

3D-SDF for HMDB0005199 ((R)-Salsolinol)

PDB for HMDB0005199 ((R)-Salsolinol)

3D PDB for HMDB0005199 ((R)-Salsolinol)

SMILES for HMDB0005199 ((R)-Salsolinol)

INCHI for HMDB0005199 ((R)-Salsolinol)

Structure for HMDB0005199 ((R)-Salsolinol)

3D Structure for HMDB0005199 ((R)-Salsolinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra