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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:10 UTC

Update Date

2023-02-21 17:17:49 UTC

HMDB ID

HMDB0012469

Secondary Accession Numbers

HMDB12469

Metabolite Identification

Common Name

(-)-Salsoline

Description

(-)-Salsoline is a compound that crystallizes from alcohol solution, melts at 221 oC, soluble in hot alcohol and chloroform; used in medicine as an antihypertensive agent. Salsoline as well as salsolinol were found in male alcoholic inpatients's urine and lumbar cerebrospinal fluid when patients were still intoxicated after a heavy alcohol debauch and after they had been inpatients and off alcohol for one week.There was a wide interindividual variation and no statistical significant difference in the levels between the first and second sampling in CSF or urine.[PMID: 6935920 ].

Structure

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

HMDB0012469
     RDKit          3D
(-)-Salsoline
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5581    2.0493   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3061    0.6839   -0.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.0757   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    0.7304   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    0.0655   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -1.3102   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -2.0009   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -1.3068    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2224   -2.0157    0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562   -2.0467   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.2572    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732    0.0914    0.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    0.6965   -0.1917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6748    2.1733   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    2.7003    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869    2.3720    0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234    2.2933   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    1.8129   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191   -3.0946    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -3.0161    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -2.9751    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.4062   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -1.2754   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.7525    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3498    0.5966    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.3517   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    2.5929   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    2.5079    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937    2.6641    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8  3  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END


  Mrv0541 02251208042D          

 14 15  0  0  1  0            999 V2000
   12.3367  -13.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1942  -13.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3367  -11.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6221  -11.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7657  -11.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7657  -12.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3367  -12.6687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0512  -11.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0512  -12.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797  -11.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797  -12.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6221  -12.2562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1942  -11.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1942  -12.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  6  0  0  0
  2 14  1  0  0  0  0
  3  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4 12  1  0  0  0  0
  5 10  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  2  0  0  0  0
  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012469

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(CCN[C@H]2C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m0/s1

> <INCHI_KEY>
YTPRLBGPGZHUPD-ZETCQYMHSA-N

> <FORMULA>
C11H15NO2

> <MOLECULAR_WEIGHT>
193.2423

> <EXACT_MASS>
193.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.296754736261757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.1372350989211433

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.097057373401725

> <JCHEM_PKA_STRONGEST_BASIC>
9.072264497646431

> <JCHEM_POLAR_SURFACE_AREA>
41.489999999999995

> <JCHEM_REFRACTIVITY>
55.478500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salsoline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012469
     RDKit          3D
(-)-Salsoline
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5581    2.0493   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3061    0.6839   -0.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.0757   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    0.7304   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    0.0655   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -1.3102   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -2.0009   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -1.3068    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2224   -2.0157    0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562   -2.0467   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.2572    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732    0.0914    0.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    0.6965   -0.1917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6748    2.1733   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    2.7003    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869    2.3720    0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234    2.2933   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    1.8129   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191   -3.0946    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -3.0161    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -2.9751    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.4062   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -1.2754   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.7525    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3498    0.5966    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.3517   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    2.5929   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    2.5079    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937    2.6641    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8  3  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      23.029 -25.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.363 -25.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.029 -20.569   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.695 -21.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.696 -20.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.696 -23.648   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.029 -23.648   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.362 -21.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.362 -22.878   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.029 -21.338   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.029 -22.878   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      21.695 -22.878   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      28.363 -20.569   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      28.363 -23.648   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   14                                                            
CONECT    3    8    4                                                       
CONECT    4    3   12                                                       
CONECT    5   10    8                                                       
CONECT    6    9   11                                                       
CONECT    7    1    9   12                                                  
CONECT    8    3    5    9                                                  
CONECT    9    6    7    8                                                  
CONECT   10    5   11   13                                                  
CONECT   11    6   10   14                                                  
CONECT   12    4    7                                                       
CONECT   13   10                                                            
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0012469
HETATM    1  C1  UNL     1       3.558   2.049  -0.077  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.306   0.684  -0.032  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.073   0.076  -0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.867   0.730  -0.112  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.338   0.065  -0.125  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.332  -1.310  -0.071  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.850  -2.001  -0.006  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.035  -1.307   0.005  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.222  -2.016   0.071  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.656  -2.047  -0.085  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.769  -1.257   0.504  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.473   0.091   0.855  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.663   0.697  -0.192  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.675   2.173  -0.180  1.00  0.00           C  
HETATM   15  H1  UNL     1       2.697   2.700   0.097  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.387   2.372   0.599  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.923   2.293  -1.116  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.878   1.813  -0.154  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.819  -3.095   0.036  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.192  -3.016   0.109  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.526  -2.975   0.526  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.861  -2.406  -1.118  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.620  -1.275  -0.226  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.193  -1.753   1.426  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.350   0.597   1.030  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.132   0.352  -1.160  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.670   2.593  -1.207  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.658   2.508   0.261  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.894   2.664   0.393  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   18
CONECT    5    6    6   13
CONECT    6    7   10
CONECT    7    8    8   19
CONECT    8    9
CONECT    9   20
CONECT   10   11   21   22
CONECT   11   12   23   24
CONECT   12   13   25
CONECT   13   14   26
CONECT   14   27   28   29
END

HMDB0012469
     RDKit          3D
(-)-Salsoline
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5581    2.0493   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3061    0.6839   -0.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.0757   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    0.7304   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    0.0655   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -1.3102   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -2.0009   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -1.3068    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2224   -2.0157    0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562   -2.0467   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.2572    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732    0.0914    0.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    0.6965   -0.1917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6748    2.1733   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    2.7003    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869    2.3720    0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234    2.2933   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    1.8129   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191   -3.0946    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -3.0161    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -2.9751    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -2.4062   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -1.2754   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.7525    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3498    0.5966    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.3517   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    2.5929   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    2.5079    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937    2.6641    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8  3  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Salsoline	MeSH
(S)-Salsoline	MeSH
1(R),2(N)-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	MeSH
7-O-Methylsalsolinol	MeSH
D-Salosine	MeSH
N-Methyl-(R)-salsolinol	MeSH
Methylsalsolinol	MeSH
Salsoline	MeSH
Salsoline (-)-form	MeSH
Salsoline hydrochloride	MeSH
Salsoline hydrochloride, (R)-isomer	MeSH
Salsoline hydrochloride, (S)-isomer	MeSH
Salsoline hydrochloride, hydrate (4:4:1)	MeSH
(1S)-7-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol	HMDB

Chemical Formula

C₁₁H₁₅NO₂

Average Molecular Weight

193.2423

Monoisotopic Molecular Weight

193.110278729

IUPAC Name

(1S)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol

Traditional Name

salsoline

CAS Registry Number

89-31-6

SMILES

COC1=CC2=C(CCN[C@H]2C)C=C1O

InChI Identifier

InChI=1S/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m0/s1

InChI Key

YTPRLBGPGZHUPD-ZETCQYMHSA-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
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:112 )

Ontology

Not Available

Endogenous (HMDB: HMDB0012469)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221.5 °C	Not Available
Boiling Point	412.25 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.688 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	0.92	ALOGPS
logP	1.14	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.1	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	55.48 m³·mol⁻¹	ChemAxon
Polarizability	21.3 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]+	143.268	31661259
DarkChem	[M-H]-	143.591	31661259
DeepCCS	[M+H]+	144.148	30932474
DeepCCS	[M-H]-	141.79	30932474
DeepCCS	[M-2H]-	176.242	30932474
DeepCCS	[M+Na]+	151.624	30932474
AllCCS	[M+H]+	143.6	32859911
AllCCS	[M+H-H2O]+	139.3	32859911
AllCCS	[M+NH4]+	147.5	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	146.2	32859911
AllCCS	[M+Na-2H]-	146.7	32859911
AllCCS	[M+HCOO]-	147.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	1.87 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0976 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	764.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	250.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	266.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	257.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	484.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	634.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	147.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	666.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	524.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	444.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	129.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Salsoline	COC1=CC2=C(CCN[C@H]2C)C=C1O	2670.7	Standard polar	33892256
(-)-Salsoline	COC1=CC2=C(CCN[C@H]2C)C=C1O	1735.9	Standard non polar	33892256
(-)-Salsoline	COC1=CC2=C(CCN[C@H]2C)C=C1O	1782.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Salsoline,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CCN[C@H]2C	1841.4	Semi standard non polar	33892256
(-)-Salsoline,1TMS,isomer #2	COC1=CC2=C(C=C1O)CCN([Si](C)(C)C)[C@H]2C	1887.7	Semi standard non polar	33892256
(-)-Salsoline,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CCN([Si](C)(C)C)[C@H]2C	1929.7	Semi standard non polar	33892256
(-)-Salsoline,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CCN([Si](C)(C)C)[C@H]2C	1958.0	Standard non polar	33892256
(-)-Salsoline,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CCN([Si](C)(C)C)[C@H]2C	2153.8	Standard polar	33892256
(-)-Salsoline,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CCN[C@H]2C	2095.5	Semi standard non polar	33892256
(-)-Salsoline,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)[C@H]2C	2136.7	Semi standard non polar	33892256
(-)-Salsoline,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CCN([Si](C)(C)C(C)(C)C)[C@H]2C	2406.6	Semi standard non polar	33892256
(-)-Salsoline,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CCN([Si](C)(C)C(C)(C)C)[C@H]2C	2432.4	Standard non polar	33892256
(-)-Salsoline,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CCN([Si](C)(C)C(C)(C)C)[C@H]2C	2447.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Salsoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-0900000000-46a08ac1000ef9e8d2e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Salsoline GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-7790000000-6cf66e441b1984402c51	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Salsoline 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 10V, Positive-QTOF	splash10-0006-0900000000-60174f1cf4cc1f4b4834	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 20V, Positive-QTOF	splash10-0006-0900000000-503253f6315fa936ceab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 40V, Positive-QTOF	splash10-0072-2900000000-65a6dbd945d9089bf6ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 10V, Negative-QTOF	splash10-0006-0900000000-00e30f946db869ed3635	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 20V, Negative-QTOF	splash10-0006-0900000000-919b64fcfb6b74a436dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 40V, Negative-QTOF	splash10-01ea-4900000000-b5c88563d80dfdd1ba10	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 10V, Negative-QTOF	splash10-0006-0900000000-5326ed117e0a68853a6c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 20V, Negative-QTOF	splash10-0006-1900000000-4e91134b5e3127909ce9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 40V, Negative-QTOF	splash10-0006-2900000000-0a98cc8b818bd78f9081	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 10V, Positive-QTOF	splash10-0006-0900000000-093c204a145d72b06e8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 20V, Positive-QTOF	splash10-002f-0900000000-5fcd8088e3a540d3cdaf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Salsoline 40V, Positive-QTOF	splash10-0ae9-3900000000-ba42a8e3e1235ca4e8c2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442356

PDB ID

Not Available

ChEBI ID

761542

Food Biomarker Ontology

Not Available

VMH ID

C09640

MarkerDB ID

Not Available

Good Scents ID

rw1192791

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Borg S, Kvande H, Magnuson E, Sjoqvist B: Salsolinol and salsoline in cerebrospinal lumbar fluid of alcoholic patients. Acta Psychiatr Scand Suppl. 1980;286:171-7. [PubMed:6935920 ]

Showing metabocard for (-)-Salsoline (HMDB0012469)

MOL for HMDB0012469 ((-)-Salsoline)

3D MOL for HMDB0012469 ((-)-Salsoline)

3D SDF for HMDB0012469 ((-)-Salsoline)

3D-SDF for HMDB0012469 ((-)-Salsoline)

PDB for HMDB0012469 ((-)-Salsoline)

3D PDB for HMDB0012469 ((-)-Salsoline)

SMILES for HMDB0012469 ((-)-Salsoline)

INCHI for HMDB0012469 ((-)-Salsoline)

Structure for HMDB0012469 ((-)-Salsoline)

3D Structure for HMDB0012469 ((-)-Salsoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra