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Showing metabocard for (R)-Salsolinol (HMDB0005199)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-12-06 15:50:25 UTC
Update Date2023-02-21 17:17:07 UTC
HMDB IDHMDB0005199
Secondary Accession Numbers
  • HMDB05199
Metabolite Identification
Common Name(R)-Salsolinol
DescriptionSalsolinol 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
Data?1676999827
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005199 ((R)-Salsolinol)


  Mrv0541 02231220212D          

 13 14  0  0  0  0            999 V2000
   14.5340   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8196   -7.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8196   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5340   -6.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2484   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2484   -7.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1051   -8.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1051   -6.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6774   -7.7344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6774   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -6.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -8.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12  5  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
Download

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

HMDB0005199
     RDKit          3D
(R)-Salsolinol
 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.6220   -2.2440    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.7812    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.0931   -0.7428 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134    1.2803   -0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0529    1.9641    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386    1.0391    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.5782   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5102    0.7778   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020    1.3274   -0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327   -0.5822    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477   -1.4041    0.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -1.1232    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415   -0.3212    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -2.5986    1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9523   -2.8425   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -2.4688    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179   -0.3618    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -0.2086   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0599    1.3289    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034    1.8165   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    2.3479    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    2.8198   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.6664   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864    0.6879   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -2.3952    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9258   -2.2097    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  2  1  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

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


  Mrv0541 02231220212D          

 13 14  0  0  0  0            999 V2000
   14.5340   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8196   -7.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8196   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5340   -6.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2484   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2484   -7.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1051   -8.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1051   -6.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6774   -7.7344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6774   -6.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -6.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9630   -8.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12  5  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005199

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H13NO2

> <MOLECULAR_WEIGHT>
179.2157

> <EXACT_MASS>
179.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.244509405439587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
0.9552438079642722

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.826094475599017

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.611087795190658

> <JCHEM_PKA_STRONGEST_BASIC>
8.695940355610801

> <JCHEM_POLAR_SURFACE_AREA>
52.49

> <JCHEM_REFRACTIVITY>
50.9962

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-salsolinol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

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

HMDB0005199
     RDKit          3D
(R)-Salsolinol
 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.6220   -2.2440    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.7812    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.0931   -0.7428 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134    1.2803   -0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0529    1.9641    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386    1.0391    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.5782   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5102    0.7778   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020    1.3274   -0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327   -0.5822    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477   -1.4041    0.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -1.1232    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415   -0.3212    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -2.5986    1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9523   -2.8425   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -2.4688    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179   -0.3618    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -0.2086   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0599    1.3289    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034    1.8165   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    2.3479    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    2.8198   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.6664   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864    0.6879   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -2.3952    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9258   -2.2097    0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  2  1  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

PDB for HMDB0005199 ((R)-Salsolinol)

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

COMPND    HMDB0005199
HETATM    1  C1  UNL     1      -1.622  -2.244   0.312  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.424  -0.781   0.290  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.190  -0.093  -0.743  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.313   1.280  -0.375  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.053   1.964   0.003  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.139   1.039   0.024  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.389   1.578  -0.101  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.510   0.778  -0.088  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.802   1.327  -0.216  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.333  -0.582   0.055  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.448  -1.404   0.070  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.069  -1.123   0.180  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.042  -0.321   0.166  1.00  0.00           C  
HETATM   14  H1  UNL     1      -1.502  -2.599   1.378  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.952  -2.842  -0.299  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.676  -2.469   0.048  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.818  -0.362   1.264  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.744  -0.209  -1.673  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.060   1.329   0.471  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.803   1.816  -1.213  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.126   2.348   1.061  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.821   2.820  -0.660  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.522   2.666  -0.215  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.586   0.688  -0.199  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.421  -2.395   0.168  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.926  -2.210   0.294  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13   17
CONECT    3    4   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7   13
CONECT    7    8   23
CONECT    8    9   10   10
CONECT    9   24
CONECT   10   11   12
CONECT   11   25
CONECT   12   13   13   26
END
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SMILES for HMDB0005199 ((R)-Salsolinol)

CC1NCCC2=C1C=C(O)C(O)=C2
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INCHI for HMDB0005199 ((R)-Salsolinol)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+)-(R)-SalsolinolHMDB
(+)-SalsolinolHMDB
(R)-(+)-SalsolinolHMDB
1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineHMDB
Salsolinol, (S)-isomerHMDB
1-Methyl-6,7-dihydroxytetrahydroisoquinolineHMDB
Salsolinol hydrobromideHMDB
SalsolinolHMDB
Salsolinol, (+-)-isomerHMDB
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional Name(+)-salsolinol
CAS Registry Number525-72-4
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 KeyIBRKLUSXDYATLG-UHFFFAOYSA-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
  • 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological 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 Solubility6.71 g/LALOGPS
logP0.16ALOGPS
logP0.96ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)8.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51 m³·mol⁻¹ChemAxon
Polarizability19.24 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]+140.83431661259
DarkChem[M-H]-137.92231661259
DeepCCS[M+H]+139.50630932474
DeepCCS[M-H]-135.67830932474
DeepCCS[M-2H]-173.19530932474
DeepCCS[M+Na]+148.73430932474
AllCCS[M+H]+139.632859911
AllCCS[M+H-H2O]+135.232859911
AllCCS[M+NH4]+143.732859911
AllCCS[M+Na]+144.932859911
AllCCS[M-H]-140.332859911
AllCCS[M+Na-2H]-140.832859911
AllCCS[M+HCOO]-141.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.5 minutes32390414
Predicted by Siyang on May 30, 20228.6173 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.0 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid194.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid456.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid253.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid80.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid149.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid37.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid268.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid230.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)649.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid577.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid50.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid635.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid159.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid174.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate572.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA489.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water267.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-SalsolinolCC1NCCC2=C1C=C(O)C(O)=C22574.3Standard polar33892256
(R)-SalsolinolCC1NCCC2=C1C=C(O)C(O)=C21791.6Standard non polar33892256
(R)-SalsolinolCC1NCCC2=C1C=C(O)C(O)=C21907.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Salsolinol,1TMS,isomer #1CC1NCCC2=CC(O)=C(O[Si](C)(C)C)C=C211878.8Semi standard non polar33892256
(R)-Salsolinol,1TMS,isomer #2CC1NCCC2=CC(O[Si](C)(C)C)=C(O)C=C211873.4Semi standard non polar33892256
(R)-Salsolinol,1TMS,isomer #3CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C1993.4Semi standard non polar33892256
(R)-Salsolinol,2TMS,isomer #1CC1NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C211905.1Semi standard non polar33892256
(R)-Salsolinol,2TMS,isomer #2CC1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C1917.5Semi standard non polar33892256
(R)-Salsolinol,2TMS,isomer #3CC1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C1921.9Semi standard non polar33892256
(R)-Salsolinol,3TMS,isomer #1CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C1990.3Semi standard non polar33892256
(R)-Salsolinol,3TMS,isomer #1CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C1967.4Standard non polar33892256
(R)-Salsolinol,3TMS,isomer #1CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C2053.2Standard polar33892256
(R)-Salsolinol,1TBDMS,isomer #1CC1NCCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C212131.8Semi standard non polar33892256
(R)-Salsolinol,1TBDMS,isomer #2CC1NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C212131.9Semi standard non polar33892256
(R)-Salsolinol,1TBDMS,isomer #3CC1C2=CC(O)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C2215.9Semi standard non polar33892256
(R)-Salsolinol,2TBDMS,isomer #1CC1NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C212375.0Semi standard non polar33892256
(R)-Salsolinol,2TBDMS,isomer #2CC1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CCN1[Si](C)(C)C(C)(C)C2426.8Semi standard non polar33892256
(R)-Salsolinol,2TBDMS,isomer #3CC1C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1[Si](C)(C)C(C)(C)C2420.0Semi standard non polar33892256
(R)-Salsolinol,3TBDMS,isomer #1CC1C2=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)C2674.2Semi standard non polar33892256
(R)-Salsolinol,3TBDMS,isomer #1CC1C2=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)C2659.2Standard non polar33892256
(R)-Salsolinol,3TBDMS,isomer #1CC1C2=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)C2463.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Salsolinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ik9-0900000000-ea926c78d9164b4155df2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Salsolinol GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-3295000000-9789c284ef49e7af9bff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Salsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOFsplash10-01q9-0900000000-2c29348adb1dba6587572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOFsplash10-01ot-0900000000-a28325af4d693ae8c6142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOFsplash10-00kb-0900000000-d89b4eb37f9694e3dbb22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-fd496b1ca2ec080ac77b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOFsplash10-03di-0900000000-2894c6730bbdd8586e0d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOFsplash10-03di-0900000000-b95a812b67613811248b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOFsplash10-03di-0900000000-e65251ff89ea89a158142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol LC-ESI-ITFT , positive-QTOFsplash10-03di-0900000000-ce7a81f09123f28c4b242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOFsplash10-01ot-0900000000-2e943291c5430f91a8ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOFsplash10-00kb-0900000000-b73360d52cf5dff31b8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOFsplash10-01q9-0900000000-2821f1026dd4b464da9d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOFsplash10-01ot-0900000000-39e018ed344d997de3b02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 30V, Positive-QTOFsplash10-014i-0900000000-9e8d0f4134ccc42a82962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOFsplash10-00kb-0900000000-b99cb0412813709933012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOFsplash10-01q9-0900000000-5cd66c681b07ac5f232e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 15V, Positive-QTOFsplash10-01ot-0900000000-24e6da15427270ddc80c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 70V, Positive-QTOFsplash10-03di-0900000000-3755faa761a6e281bf8b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 55V, Positive-QTOFsplash10-03di-0900000000-be13089127e47b801b602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOFsplash10-00kb-0900000000-d45c2139d9620f895f412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 10V, Positive-QTOFsplash10-001i-0900000000-1c070d491bdf6a8f80d32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 20V, Positive-QTOFsplash10-001i-0900000000-7a8e025141a2d1299eb42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 40V, Positive-QTOFsplash10-06y9-3900000000-bed1ede28e58e633dcbe2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 10V, Negative-QTOFsplash10-004i-0900000000-f913db2f113ff2f73d082015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 20V, Negative-QTOFsplash10-004i-0900000000-726420a5901821528a902015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Salsolinol 40V, Negative-QTOFsplash10-03dl-5900000000-aaac23c6385c30ec14b52015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00042 +/- 0.000094 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0022 +/- 0.0015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0010 +/- 0.00043 uMAdult (>18 years old)BothHypertension details
BloodDetected and Quantified0.0019 +/- 0.00078 uMAdult (>18 years old)BothAfter alcohol intake details
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.001 uMAdult (>18 years old)Not SpecifiedParkinson's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.001 uMAdult (>18 years old)Not SpecifiedMultiple System Atrophy (MSA) details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Hypertension
  1. 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
  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 ]
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 ]
Colorectal cancer
  1. 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 ]
  2. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018047
KNApSAcK IDNot Available
Chemspider ID49181
KEGG Compound IDC09642
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54456
PDB IDNot Available
ChEBI ID123715
Food Biomarker OntologyNot Available
VMH IDC09642
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKovacs, 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 ]
  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 ]
  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 ]