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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:12 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029567

Secondary Accession Numbers

HMDB29567

Metabolite Identification

Common Name

Hydroxy-alpha-sanshool

Description

Hydroxy-alpha-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. Thus, hydroxy-alpha-sanshool is considered to be a fatty amide. Based on a literature review a small amount of articles have been published on Hydroxy-alpha-sanshool.

Structure

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

HMDB0029567
     RDKit          3D
Hydroxy-alpha-sanshool
 44 43  0  0  0  0  0  0  0  0999 V2000
    8.3998    0.2242   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9955   -1.0055    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085   -1.2857    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.3860   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.7015    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827    0.1988   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.0222   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1668    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.6428    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    0.1900    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632   -0.1006    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.7399    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790    1.8587   -0.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078    0.4806    0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9686    1.2601   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2178    0.3945   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9288   -0.9120   -1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3469    1.0956   -1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4926    0.0899    0.8944 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4936    0.2668   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239    1.0903    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9302    0.2692   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7599   -1.6470    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3956   -2.1684    1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249    0.5026   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -1.5883    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0957   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    0.6885   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.6542   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.9557    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2681   -0.0921    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -1.5358    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    1.0774    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.9757    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.7083   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    1.5221   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649    2.1948    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -0.7542   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8742   -1.4603   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464   -1.5324   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3886    2.1538   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2942    0.5638   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1452    1.0658   -2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507    0.8559    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 15 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
 19 44  1  0
M  END


  Mrv0541 05061304492D          

 19 18  0  0  0  0            999 V2000
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  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
 13 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029567

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

> <INCHI_KEY>
LHFKHAVGGJJQFF-JRNWQWJGSA-N

> <FORMULA>
C16H25NO2

> <MOLECULAR_WEIGHT>
263.3752

> <EXACT_MASS>
263.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.04834034218719

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.6337538973333334

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.035121126665373

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493271092456638

> <JCHEM_PKA_STRONGEST_BASIC>
4.954677333239283

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
85.7126

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029567
     RDKit          3D
Hydroxy-alpha-sanshool
 44 43  0  0  0  0  0  0  0  0999 V2000
    8.3998    0.2242   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9955   -1.0055    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085   -1.2857    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.3860   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.7015    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827    0.1988   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.0222   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1668    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.6428    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    0.1900    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632   -0.1006    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.7399    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790    1.8587   -0.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078    0.4806    0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9686    1.2601   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2178    0.3945   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9288   -0.9120   -1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3469    1.0956   -1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4926    0.0899    0.8944 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4936    0.2668   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239    1.0903    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9302    0.2692   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7599   -1.6470    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3956   -2.1684    1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249    0.5026   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -1.5883    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0957   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    0.6885   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.6542   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.9557    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2681   -0.0921    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -1.5358    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    1.0774    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.9757    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.7083   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    1.5221   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649    2.1948    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -0.7542   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8742   -1.4603   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464   -1.5324   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3886    2.1538   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2942    0.5638   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1452    1.0658   -2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507    0.8559    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 15 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
 19 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.860   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.090   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.780   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -3.437   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4    1    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                                                       
CONECT   13   12   15                                                       
CONECT   14   16   17                                                       
CONECT   15   13   17   18                                                  
CONECT   16    2    3   14   19                                             
CONECT   17   14   15                                                       
CONECT   18   15                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0029567
HETATM    1  C1  UNL     1       8.400   0.224  -0.286  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.996  -1.005   0.455  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.709  -1.286   0.549  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.742  -0.386  -0.071  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.432  -0.702   0.044  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.483   0.199  -0.575  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.200  -0.022  -0.518  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.599  -1.167   0.156  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.681  -0.643   1.265  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.353   0.190   0.628  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.663  -0.101   0.725  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.669   0.740   0.084  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.279   1.859  -0.638  1.00  0.00           O  
HETATM   14  N1  UNL     1      -3.908   0.481   0.166  1.00  0.00           N  
HETATM   15  C13 UNL     1      -4.969   1.260  -0.438  1.00  0.00           C  
HETATM   16  C14 UNL     1      -6.218   0.394  -0.431  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.929  -0.912  -1.154  1.00  0.00           C  
HETATM   18  C16 UNL     1      -7.347   1.096  -1.121  1.00  0.00           C  
HETATM   19  O2  UNL     1      -6.493   0.090   0.894  1.00  0.00           O  
HETATM   20  H1  UNL     1       9.494   0.267  -0.440  1.00  0.00           H  
HETATM   21  H2  UNL     1       8.124   1.090   0.330  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.930   0.269  -1.298  1.00  0.00           H  
HETATM   23  H4  UNL     1       8.760  -1.647   0.902  1.00  0.00           H  
HETATM   24  H5  UNL     1       6.396  -2.168   1.080  1.00  0.00           H  
HETATM   25  H6  UNL     1       6.025   0.503  -0.607  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.171  -1.588   0.582  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.832   1.096  -1.112  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.522   0.689  -1.007  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.901  -1.654  -0.600  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.252  -1.956   0.502  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.268  -0.092   2.028  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.276  -1.536   1.762  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.145   1.077   0.051  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.947  -0.976   1.292  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.597   1.708  -1.398  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.766   1.522  -1.489  1.00  0.00           H  
HETATM   37  H18 UNL     1      -5.165   2.195   0.100  1.00  0.00           H  
HETATM   38  H19 UNL     1      -5.446  -0.754  -2.133  1.00  0.00           H  
HETATM   39  H20 UNL     1      -6.874  -1.460  -1.328  1.00  0.00           H  
HETATM   40  H21 UNL     1      -5.246  -1.532  -0.515  1.00  0.00           H  
HETATM   41  H22 UNL     1      -7.389   2.154  -0.831  1.00  0.00           H  
HETATM   42  H23 UNL     1      -8.294   0.564  -0.869  1.00  0.00           H  
HETATM   43  H24 UNL     1      -7.145   1.066  -2.210  1.00  0.00           H  
HETATM   44  H25 UNL     1      -6.351   0.856   1.502  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   23
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   14   14
CONECT   13   35
CONECT   14   15
CONECT   15   16   36   37
CONECT   16   17   18   19
CONECT   17   38   39   40
CONECT   18   41   42   43
CONECT   19   44
END

HMDB0029567
     RDKit          3D
Hydroxy-alpha-sanshool
 44 43  0  0  0  0  0  0  0  0999 V2000
    8.3998    0.2242   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9955   -1.0055    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085   -1.2857    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.3860   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.7015    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827    0.1988   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.0222   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1668    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.6428    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    0.1900    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632   -0.1006    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    0.7399    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790    1.8587   -0.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078    0.4806    0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9686    1.2601   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2178    0.3945   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9288   -0.9120   -1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3469    1.0956   -1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4926    0.0899    0.8944 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4936    0.2668   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239    1.0903    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9302    0.2692   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7599   -1.6470    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3956   -2.1684    1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249    0.5026   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -1.5883    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0957   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    0.6885   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -1.6542   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.9557    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2681   -0.0921    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -1.5358    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    1.0774    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.9757    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.7083   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    1.5221   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649    2.1948    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -0.7542   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8742   -1.4603   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464   -1.5324   -0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3886    2.1538   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2942    0.5638   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1452    1.0658   -2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507    0.8559    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 15 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
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hydroxy-a-sanshool	Generator
Hydroxy-α-sanshool	Generator

Chemical Formula

C₁₆H₂₅NO₂

Average Molecular Weight

263.3752

Monoisotopic Molecular Weight

263.188529049

IUPAC Name

(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

Traditional Name

(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

CAS Registry Number

83883-10-7

SMILES

C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O

InChI Identifier

InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

InChI Key

LHFKHAVGGJJQFF-JRNWQWJGSA-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
Tertiary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0029567)
Cell membrane (HMDB: HMDB0029567)

Biofluid or Excreta

Urine (HMDB: HMDB0029567)

Cellular substructure

Extracellular (HMDB: HMDB0029567)
Membrane (HMDB: HMDB0029567)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029567)

Source

Endogenous

Endogenous (HMDB: HMDB0029567)

Plant

Plant (HMDB: HMDB0029567)

Animal

Animal (HMDB: HMDB0029567)

Exogenous

Food

Food (HMDB: HMDB0029567)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0029567)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0029567)

Cellular process

Cell signaling (HMDB: HMDB0029567)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0029567)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0029567)

Nutrient

Nutrient (HMDB: HMDB0029567)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029567)

Emulsifier (HMDB: HMDB0029567)

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	33.25 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0072 g/L	ALOGPS
logP	4.28	ALOGPS
logP	3.63	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.71 m³·mol⁻¹	ChemAxon
Polarizability	32.05 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	176.624	30932474
DeepCCS	[M-H]-	174.266	30932474
DeepCCS	[M-2H]-	207.152	30932474
DeepCCS	[M+Na]+	182.717	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	171.5	32859911
AllCCS	[M+Na]+	172.4	32859911
AllCCS	[M-H]-	167.9	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	170.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxy-alpha-sanshool	C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O	3403.3	Standard polar	33892256
Hydroxy-alpha-sanshool	C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O	2161.5	Standard non polar	33892256
Hydroxy-alpha-sanshool	C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O	2163.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxy-alpha-sanshool,1TMS,isomer #1	C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O)O[Si](C)(C)C	2277.8	Semi standard non polar	33892256
Hydroxy-alpha-sanshool,1TMS,isomer #2	C/C=C\C=C\C=C/CC/C=C/C(O)=N/CC(C)(C)O[Si](C)(C)C	2390.1	Semi standard non polar	33892256
Hydroxy-alpha-sanshool,2TMS,isomer #1	C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	2373.7	Semi standard non polar	33892256
Hydroxy-alpha-sanshool,1TBDMS,isomer #1	C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O)O[Si](C)(C)C(C)(C)C	2488.8	Semi standard non polar	33892256
Hydroxy-alpha-sanshool,1TBDMS,isomer #2	C/C=C\C=C\C=C/CC/C=C/C(O)=N/CC(C)(C)O[Si](C)(C)C(C)(C)C	2590.0	Semi standard non polar	33892256
Hydroxy-alpha-sanshool,2TBDMS,isomer #1	C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2781.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9640000000-d766379807b67f8a7da0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (2 TMS) - 70eV, Positive	splash10-001i-4944000000-655cbc0bdbbccd2125b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxy-alpha-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 - Hydroxy-alpha-sanshool 10V, Positive-QTOF	splash10-01pa-9170000000-3edf9fccda30235c896e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Positive-QTOF	splash10-0079-9110000000-0eaf0328825abe309bb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Positive-QTOF	splash10-00di-9100000000-76c392bd8a883d23e47d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Negative-QTOF	splash10-03di-0190000000-9dbd64116f2a467ceee5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Negative-QTOF	splash10-03dm-4980000000-1519aa203de14b7afb3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Negative-QTOF	splash10-007d-9700000000-d3dbe3db62be5cb1ef06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Negative-QTOF	splash10-03di-2090000000-2a87acc0fe5f25aec469	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Negative-QTOF	splash10-03dr-8980000000-aa93cc38ee943d1f0a86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Negative-QTOF	splash10-00kr-9800000000-e7d302c8b6dec6dd0a6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Positive-QTOF	splash10-03di-2490000000-87d182707bad1650856f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Positive-QTOF	splash10-001l-9310000000-c70cb4872bbd1bd4df9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Positive-QTOF	splash10-004l-9100000000-68f630af9f9cbaa0c9aa	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB000722

KNApSAcK ID

C00056374

Chemspider ID

30776781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxy alpha sanshool

METLIN ID

Not Available

PubChem Compound

46870578

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Hydroxy-alpha-sanshool (HMDB0029567)

MOL for HMDB0029567 (Hydroxy-alpha-sanshool)

3D MOL for HMDB0029567 (Hydroxy-alpha-sanshool)

3D SDF for HMDB0029567 (Hydroxy-alpha-sanshool)

3D-SDF for HMDB0029567 (Hydroxy-alpha-sanshool)

PDB for HMDB0029567 (Hydroxy-alpha-sanshool)

3D PDB for HMDB0029567 (Hydroxy-alpha-sanshool)

SMILES for HMDB0029567 (Hydroxy-alpha-sanshool)

INCHI for HMDB0029567 (Hydroxy-alpha-sanshool)

Structure for HMDB0029567 (Hydroxy-alpha-sanshool)

3D Structure for HMDB0029567 (Hydroxy-alpha-sanshool)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra