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

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:43 UTC

Update Date

2024-04-30 19:32:25 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 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

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

Molecular Formula

C₁₀H₁₃NO₂

Average Mass

179.2157

Monoisotopic Mass

179.094628665

IUPAC Name

1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

(+)-salsolinol

CAS Registry Number

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ik9-0900000000-ea926c78d9164b4155df	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-3295000000-9789c284ef49e7af9bff	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01q9-0900000000-2c29348adb1dba658757	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ot-0900000000-a28325af4d693ae8c614	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-0900000000-d89b4eb37f9694e3dbb2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-fd496b1ca2ec080ac77b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-2894c6730bbdd8586e0d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-b95a812b67613811248b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-e65251ff89ea89a15814	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-ce7a81f09123f28c4b24	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-01ot-0900000000-2e943291c5430f91a8ff	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0900000000-b73360d52cf5dff31b8d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-2821f1026dd4b464da9d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-01ot-0900000000-39e018ed344d997de3b0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-9e8d0f4134ccc42a8296	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0900000000-b99cb041281370993301	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-5cd66c681b07ac5f232e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-01ot-0900000000-24e6da15427270ddc80c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 70V, Positive	splash10-03di-0900000000-3755faa761a6e281bf8b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-03di-0900000000-be13089127e47b801b60	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0900000000-d45c2139d9620f895f41	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-1c070d491bdf6a8f80d3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-7a8e025141a2d1299eb4	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06y9-3900000000-bed1ede28e58e633dcbe	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-f913db2f113ff2f73d08	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-726420a5901821528a90	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-5900000000-aaac23c6385c30ec14b5	2015-04-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

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

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004124	Acetaldehyde	(R)-Salsolinol	Not Available	RE1918C	VMH	10556560 8891913
MMDBr0004128	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available	Catechol O-Methyltransferase	VMH	10556560 8891913
MMDBr0004129	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available	Catechol O-Methyltransferase	VMH	10556560 8891913
MMDBr0004248	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available	RE2384C	VMH	11008878
MMDBr0008872	(R)-Salsolinol	(R)-Salsolinol	Solute carrier family 22 (organic cation transporter), member 2	Facilitated Diffusion Through Uniport Oct2 into Extracellular Space	VMH	30371894

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	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

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Plant	Annona reticulata	FooDB	31437929
Plant	Seed	Theobroma cacao	FooDB	31437929

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

HMDB0005199

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

References

Synthesis Reference

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:0x00007fa4b2b18448>

3D MOL for #<Metabolite:0x00007fa4b2b18448>

3D SDF for #<Metabolite:0x00007fa4b2b18448>

3D-SDF for #<Metabolite:0x00007fa4b2b18448>

PDB for #<Metabolite:0x00007fa4b2b18448>

3D PDB for #<Metabolite:0x00007fa4b2b18448>

SMILES for #<Metabolite:0x00007fa4b2b18448>

INCHI for #<Metabolite:0x00007fa4b2b18448>

Structure for #<Metabolite:0x00007fa4b2b18448>

3D Structure for #<Metabolite:0x00007fa4b2b18448>