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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:38:33 UTC

Update Date

2022-11-23 21:48:33 UTC

HMDB ID

HMDB0249150

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Sanshool

Description

Sanshool, also known as alpha-sanshool or beta-sanshool, belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Based on a literature review a significant number of articles have been published on Sanshool. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-sanshool is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-Sanshool 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

HMDB0249150
     RDKit          3D
beta-sanshool
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.2814   -2.4741   -4.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -2.8190   -3.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4713   -2.2090   -2.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987   -1.0348   -3.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151   -0.4304   -2.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544    0.7104   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    1.3292   -2.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377    0.8626   -1.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730    2.0053   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.3837    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226    1.7275    1.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153    0.9244    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.0219    2.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    1.1860    3.0212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661    1.4525    3.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7774    0.3103    3.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -0.9440    4.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172    0.0236    2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837   -3.1909   -5.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -1.4240   -4.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3656   -2.6651   -4.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8861   -3.6971   -2.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9921   -2.5873   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3472   -0.6982   -4.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299   -0.8333   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807    1.0928   -4.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    2.1807   -3.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -0.0584   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.7402   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    2.1361   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.9009   -1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.5181    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    2.5377    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030    0.1401    3.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040    2.3253    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.8072    4.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608    0.6519    4.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5285   -1.4664    3.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.6970    5.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0587   -1.6459    4.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    0.9857    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3585   -0.3920    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0901   -0.6436    2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  END


  Mrv1533004161513282D          

 18 17  0  0  0  0            999 V2000
   -7.3362    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249150

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=CC=CC=CCCC=CC(=O)NCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)

> <INCHI_KEY>
SBXYHCVXUCYYJT-UHFFFAOYSA-N

> <FORMULA>
C16H25NO

> <MOLECULAR_WEIGHT>
247.382

> <EXACT_MASS>
247.193614429

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.712643731451656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2-methylpropyl)dodeca-2,6,8,10-tetraenamide

> <ALOGPS_LOGP>
4.74

> <JCHEM_LOGP>
4.051403265333334

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.371682665861382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.09274180143298871

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
83.5858

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-methylpropyl)dodeca-2,6,8,10-tetraenamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249150
     RDKit          3D
beta-sanshool
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.2814   -2.4741   -4.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -2.8190   -3.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4713   -2.2090   -2.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987   -1.0348   -3.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151   -0.4304   -2.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544    0.7104   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    1.3292   -2.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377    0.8626   -1.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730    2.0053   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.3837    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226    1.7275    1.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153    0.9244    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.0219    2.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    1.1860    3.0212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661    1.4525    3.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7774    0.3103    3.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -0.9440    4.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172    0.0236    2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837   -3.1909   -5.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -1.4240   -4.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3656   -2.6651   -4.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8861   -3.6971   -2.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9921   -2.5873   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3472   -0.6982   -4.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299   -0.8333   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807    1.0928   -4.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    2.1807   -3.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -0.0584   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.7402   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    2.1361   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.9009   -1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.5181    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    2.5377    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030    0.1401    3.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040    2.3253    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.8072    4.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608    0.6519    4.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5285   -1.4664    3.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.6970    5.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0587   -1.6459    4.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    0.9857    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3585   -0.3920    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0901   -0.6436    2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0     -13.694   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.360   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.027   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.693   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.359   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.977  -0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0249150
HETATM    1  C1  UNL     1       6.281  -2.474  -4.259  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.518  -2.819  -3.069  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.471  -2.209  -2.629  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.899  -1.035  -3.318  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.815  -0.430  -2.798  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.254   0.710  -3.468  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.168   1.329  -2.965  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.538   0.863  -1.749  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.573   2.005  -0.697  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.037   1.384   0.498  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.123   1.727   1.127  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.515   0.924   2.312  1.00  0.00           C  
HETATM   13  O1  UNL     1      -0.662  -0.022   2.533  1.00  0.00           O  
HETATM   14  N1  UNL     1      -2.614   1.186   3.021  1.00  0.00           N  
HETATM   15  C13 UNL     1      -3.766   1.453   3.772  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.777   0.310   3.777  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.222  -0.944   4.368  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.217   0.024   2.341  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.084  -3.191  -5.099  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.133  -1.424  -4.556  1.00  0.00           H  
HETATM   21  H3  UNL     1       7.366  -2.665  -4.000  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.886  -3.697  -2.500  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.992  -2.587  -1.713  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.347  -0.698  -4.235  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.430  -0.833  -1.909  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.681   1.093  -4.369  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.820   2.181  -3.550  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.869  -0.058  -1.305  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.568   0.740  -1.958  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.662   2.136  -0.523  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.083   2.901  -1.070  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.546   0.518   0.877  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.753   2.538   0.855  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.303   0.140   3.879  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.304   2.325   3.282  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.601   1.807   4.835  1.00  0.00           H  
HETATM   37  H19 UNL     1      -5.661   0.652   4.306  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.529  -1.466   3.698  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.757  -0.697   5.348  1.00  0.00           H  
HETATM   40  H22 UNL     1      -5.059  -1.646   4.574  1.00  0.00           H  
HETATM   41  H23 UNL     1      -5.499   0.986   1.852  1.00  0.00           H  
HETATM   42  H24 UNL     1      -4.359  -0.392   1.782  1.00  0.00           H  
HETATM   43  H25 UNL     1      -6.090  -0.644   2.338  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   22
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   14
CONECT   14   15   34
CONECT   15   16   35   36
CONECT   16   17   18   37
CONECT   17   38   39   40
CONECT   18   41   42   43
END

HMDB0249150
     RDKit          3D
beta-sanshool
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.2814   -2.4741   -4.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -2.8190   -3.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4713   -2.2090   -2.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987   -1.0348   -3.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151   -0.4304   -2.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544    0.7104   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    1.3292   -2.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377    0.8626   -1.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730    2.0053   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.3837    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226    1.7275    1.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153    0.9244    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.0219    2.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    1.1860    3.0212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661    1.4525    3.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7774    0.3103    3.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -0.9440    4.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172    0.0236    2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837   -3.1909   -5.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -1.4240   -4.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3656   -2.6651   -4.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8861   -3.6971   -2.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9921   -2.5873   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3472   -0.6982   -4.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299   -0.8333   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807    1.0928   -4.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    2.1807   -3.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -0.0584   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679    0.7402   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    2.1361   -0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.9009   -1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.5181    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    2.5377    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030    0.1401    3.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040    2.3253    3.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.8072    4.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608    0.6519    4.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5285   -1.4664    3.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.6970    5.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0587   -1.6459    4.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4989    0.9857    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3585   -0.3920    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0901   -0.6436    2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Sanshool	MeSH
beta-Sanshool	MeSH
gamma-Sanshool	MeSH
N-(2-Methylpropyl)dodeca-2,6,8,10-tetraenimidate	Generator

Chemical Formula

C₁₆H₂₅NO

Average Molecular Weight

247.382

Monoisotopic Molecular Weight

247.193614429

IUPAC Name

N-(2-methylpropyl)dodeca-2,6,8,10-tetraenamide

Traditional Name

N-(2-methylpropyl)dodeca-2,6,8,10-tetraenamide

CAS Registry Number

Not Available

SMILES

CC=CC=CC=CCCC=CC(=O)NCC(C)C

InChI Identifier

InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)

InChI Key

SBXYHCVXUCYYJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.74	ALOGPS
logP	4.05	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	-0.093	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.59 m³·mol⁻¹	ChemAxon
Polarizability	31.71 Å³	ChemAxon
Number of Rings	0	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]+	160.585	30932474
DeepCCS	[M-H]-	158.227	30932474
DeepCCS	[M-2H]-	191.989	30932474
DeepCCS	[M+Na]+	166.917	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	167.9	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	165.7	32859911
AllCCS	[M+Na-2H]-	166.7	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-sanshool	CC=CC=CC=CCCC=CC(=O)NCC(C)C	3070.6	Standard polar	33892256
beta-sanshool	CC=CC=CC=CCCC=CC(=O)NCC(C)C	2091.3	Standard non polar	33892256
beta-sanshool	CC=CC=CC=CCCC=CC(=O)NCC(C)C	2236.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-sanshool,1TMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C	2193.3	Semi standard non polar	33892256
beta-sanshool,1TMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C	2253.7	Standard non polar	33892256
beta-sanshool,1TMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C	2369.0	Standard polar	33892256
beta-sanshool,1TBDMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C(C)(C)C	2379.1	Semi standard non polar	33892256
beta-sanshool,1TBDMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C(C)(C)C	2440.3	Standard non polar	33892256
beta-sanshool,1TBDMS,isomer #1	CC=CC=CC=CCCC=CC(=O)N(CC(C)C)[Si](C)(C)C(C)(C)C	2474.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sanshool GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8930000000-ac8d06538d842b0255e1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sanshool 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 - beta-Sanshool 10V, Positive-QTOF	splash10-0002-5890000000-70db08eefc3defed0436	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sanshool 20V, Positive-QTOF	splash10-0ab9-9100000000-d715641e775f547a79a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sanshool 40V, Positive-QTOF	splash10-056u-9100000000-34df9fe12e9683a4f3e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sanshool 10V, Negative-QTOF	splash10-0002-0290000000-746753f68a0b2ec30ab2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sanshool 20V, Negative-QTOF	splash10-0002-3960000000-80f9ddad955da5afc160	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sanshool 40V, Negative-QTOF	splash10-014l-8900000000-56c97b52aa589479df29	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

C00039254

Chemspider ID

57523865

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxy alpha sanshool

METLIN ID

Not Available

PubChem Compound

160493

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 beta-Sanshool (HMDB0249150)

MOL for HMDB0249150 (beta-Sanshool)

3D MOL for HMDB0249150 (beta-Sanshool)

3D SDF for HMDB0249150 (beta-Sanshool)

3D-SDF for HMDB0249150 (beta-Sanshool)

PDB for HMDB0249150 (beta-Sanshool)

3D PDB for HMDB0249150 (beta-Sanshool)

SMILES for HMDB0249150 (beta-Sanshool)

INCHI for HMDB0249150 (beta-Sanshool)

Structure for HMDB0249150 (beta-Sanshool)

3D Structure for HMDB0249150 (beta-Sanshool)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra