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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 18:14:54 UTC

Update Date

2021-09-26 22:47:35 UTC

HMDB ID

HMDB0242223

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Vesamicol

Description

(-)-Vesamicol, also known as methylvesamicol, belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Based on a literature review a significant number of articles have been published on (-)-Vesamicol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-vesamicol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Vesamicol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259800
     RDKit          3D
vesamicol
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6128    1.7762    0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.8362   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000    1.1900   -1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907    0.1145   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258   -0.5094    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -0.7500    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -0.5711   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113   -1.0984   -0.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475   -1.2481   -1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.2977   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051    0.0207    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.3761    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901   -0.4199    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3234   -0.0905    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    1.0612    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520    1.8661   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213    1.5203   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.0802    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -1.0787    1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1130    1.8845    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003    0.8610   -1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742    2.1275   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.4431   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064    0.5907   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202   -0.6809   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465    0.1081    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9440   -1.4895    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    0.0174    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981   -1.7697    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -1.2027   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.3771   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -2.1806   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -2.1148   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -1.3279   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.7911   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821   -1.3083    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -0.7473    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811    1.3100    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.7704   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    2.1891   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    0.9119    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.4211    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -2.0972    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -0.9050    1.9875 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
  7  2  1  0
 19  8  1  0
 17 12  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

  Mrv1652308282120242D          

 19 21  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242223

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCCCC1N1CCC(CC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14/h1-3,6-7,15-17,19H,4-5,8-13H2

> <INCHI_KEY>
YSSBJODGIYRAMI-UHFFFAOYSA-N

> <FORMULA>
C17H25NO

> <MOLECULAR_WEIGHT>
259.393

> <EXACT_MASS>
259.193614429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.66974675027574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.1857255909999993

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.596862582921208

> <JCHEM_PKA_STRONGEST_BASIC>
9.931595969338918

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
79.14940000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vesamicol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259800
     RDKit          3D
vesamicol
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6128    1.7762    0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.8362   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000    1.1900   -1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907    0.1145   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258   -0.5094    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -0.7500    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -0.5711   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113   -1.0984   -0.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475   -1.2481   -1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.2977   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051    0.0207    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.3761    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901   -0.4199    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3234   -0.0905    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    1.0612    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520    1.8661   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213    1.5203   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.0802    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -1.0787    1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1130    1.8845    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003    0.8610   -1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742    2.1275   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.4431   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064    0.5907   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202   -0.6809   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465    0.1081    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9440   -1.4895    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    0.0174    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981   -1.7697    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -1.2027   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.3771   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -2.1806   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -2.1148   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -1.3279   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.7911   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821   -1.3083    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -0.7473    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811    1.3100    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.7704   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    2.1891   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    0.9119    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.4211    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -2.0972    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -0.9050    1.9875 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
  7  2  1  0
 19  8  1  0
 17 12  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    4                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0259800
HETATM    1  O1  UNL     1      -1.613   1.776   0.018  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.170   0.836  -0.831  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.600   1.190  -1.094  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.591   0.115  -0.791  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.426  -0.509   0.566  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.977  -0.750   0.917  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.083  -0.571  -0.300  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.811  -1.098  -0.076  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.047  -1.248  -1.203  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.499  -1.298  -0.727  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.705   0.021   0.029  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.104   0.376   0.159  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.990  -0.420   0.874  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.323  -0.090   1.006  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.814   1.061   0.418  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.952   1.866  -0.296  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.621   1.520  -0.418  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.941  -0.080   1.312  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.219  -1.079   1.184  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.113   1.885   0.866  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.600   0.861  -1.781  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.874   2.127  -0.564  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.737   1.443  -2.188  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.606   0.591  -0.801  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.620  -0.681  -1.565  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.947   0.108   1.320  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.944  -1.490   0.539  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.699   0.017   1.659  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.798  -1.770   1.308  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.586  -1.203  -1.098  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.001  -0.377  -1.888  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.132  -2.181  -1.795  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.691  -2.115  -0.032  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.185  -1.328  -1.614  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.196   0.791  -0.592  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.582  -1.308   1.318  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.977  -0.747   1.576  1.00  0.00           H  
HETATM   38  H19 UNL     1       6.881   1.310   0.531  1.00  0.00           H  
HETATM   39  H20 UNL     1       5.333   2.770  -0.759  1.00  0.00           H  
HETATM   40  H21 UNL     1       2.969   2.189  -0.996  1.00  0.00           H  
HETATM   41  H22 UNL     1       0.512   0.912   1.560  1.00  0.00           H  
HETATM   42  H23 UNL     1       1.525  -0.421   2.174  1.00  0.00           H  
HETATM   43  H24 UNL     1       0.227  -2.097   1.389  1.00  0.00           H  
HETATM   44  H25 UNL     1      -0.931  -0.905   1.988  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3    7   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30
CONECT    8    9   19
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   18   35
CONECT   12   13   13   17
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   40
CONECT   18   19   41   42
CONECT   19   43   44
END

HMDB0259800
     RDKit          3D
vesamicol
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6128    1.7762    0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.8362   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000    1.1900   -1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907    0.1145   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258   -0.5094    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -0.7500    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825   -0.5711   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113   -1.0984   -0.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475   -1.2481   -1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.2977   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051    0.0207    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.3761    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901   -0.4199    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3234   -0.0905    1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141    1.0612    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520    1.8661   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213    1.5203   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.0802    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -1.0787    1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1130    1.8845    0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003    0.8610   -1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742    2.1275   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.4431   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064    0.5907   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202   -0.6809   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465    0.1081    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9440   -1.4895    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    0.0174    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981   -1.7697    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5861   -1.2027   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.3771   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -2.1806   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -2.1148   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -1.3279   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.7911   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821   -1.3083    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -0.7473    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811    1.3100    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.7704   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    2.1891   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    0.9119    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.4211    2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -2.0972    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -0.9050    1.9875 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
  7  2  1  0
 19  8  1  0
 17 12  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Phenylpiperidino)cyclohexanol	HMDB
Methylvesamicol	HMDB
Vesamicol hydrochloride	HMDB
2-(4-Phenyl-1-piperidinyl)cyclohexanol	HMDB

Chemical Formula

C₁₇H₂₅NO

Average Molecular Weight

259.393

Monoisotopic Molecular Weight

259.193614429

IUPAC Name

2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol

Traditional Name

vesamicol

CAS Registry Number

Not Available

SMILES

OC1CCCCC1N1CCC(CC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H25NO/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14/h1-3,6-7,15-17,19H,4-5,8-13H2

InChI Key

YSSBJODGIYRAMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Cyclohexanol
Cyclohexylamine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	3.91	ALOGPS
logP	3.19	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.15 m³·mol⁻¹	ChemAxon
Polarizability	31.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	161.927	30932474
DeepCCS	[M-H]-	159.569	30932474
DeepCCS	[M-2H]-	192.503	30932474
DeepCCS	[M+Na]+	168.02	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	168.8	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Vesamicol	OC1CCCCC1N1CCC(CC1)C1=CC=CC=C1	2258.0	Standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Vesamicol,1TMS,isomer #1	C[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2271.0	Semi standard non polar	33892256
(-)-Vesamicol,1TMS,isomer #1	C[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2437.9	Standard non polar	33892256
(-)-Vesamicol,1TMS,isomer #1	C[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2803.7	Standard polar	33892256
(-)-Vesamicol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2512.2	Semi standard non polar	33892256
(-)-Vesamicol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2672.2	Standard non polar	33892256
(-)-Vesamicol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCCCC1N1CCC(C2=CC=CC=C2)CC1	2959.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Vesamicol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uyi-3390000000-871cd8bd84da67135581	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Vesamicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Vesamicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Vesamicol 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 - (-)-Vesamicol 10V, Positive-QTOF	splash10-03di-0090000000-b9b40fb36729a37b3613	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Vesamicol 20V, Positive-QTOF	splash10-03dl-0090000000-0c0f05cd67ad12f91f38	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Vesamicol 40V, Positive-QTOF	splash10-004l-6910000000-ff27d39b8afb6f64cbb7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Vesamicol 10V, Negative-QTOF	splash10-0a4l-0090000000-f774aab043b4825cbe81	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Vesamicol 20V, Negative-QTOF	splash10-052f-0190000000-d5d8d074e0972140fb02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Vesamicol 40V, Negative-QTOF	splash10-03dr-2950000000-2d5d31cf61e55812baa2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5460

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5662

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (-)-Vesamicol (HMDB0242223)

MOL for HMDB0242223 ((-)-Vesamicol)

3D MOL for HMDB0242223 ((-)-Vesamicol)

3D SDF for HMDB0242223 ((-)-Vesamicol)

3D-SDF for HMDB0242223 ((-)-Vesamicol)

PDB for HMDB0242223 ((-)-Vesamicol)

3D PDB for HMDB0242223 ((-)-Vesamicol)

SMILES for HMDB0242223 ((-)-Vesamicol)

INCHI for HMDB0242223 ((-)-Vesamicol)

Structure for HMDB0242223 ((-)-Vesamicol)

3D Structure for HMDB0242223 ((-)-Vesamicol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra