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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:46:37 UTC

Update Date

2022-03-07 02:55:46 UTC

HMDB ID

HMDB0038457

Secondary Accession Numbers

HMDB38457

Metabolite Identification

Common Name

Dihydrocapsaicin

Description

Dihydrocapsaicin is found in pepper (C. annuum). It is a potential nutriceutical. Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Dihydrocapsaicin accounts for about 22% of the total capsaicinoids mixture and has about the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100 % ethanol.

Structure

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

HMDB0038457
     RDKit          3D
Dihydrocapsaicin
 51 51  0  0  0  0  0  0  0  0999 V2000
   -5.8258    2.6380   -1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1847    1.9095   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7734    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    0.2830   -0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.8576   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5811   -1.4094   -0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -1.9597   -0.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -1.0706    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    0.1679    0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -1.6682    1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617   -0.6424    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.0492    1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176   -0.9755    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507   -0.3060   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5823    0.7120   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3744    1.2988   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4028    1.9299   -2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    0.1939   -1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -1.5483    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1401   -1.0779    1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183    0.0662    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8652    0.5280    2.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    3.6762   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1843    2.1125   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7301    2.7567   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.8159   -1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -2.2419   -1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.6585   -1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -2.9804    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -2.5211    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -2.1690    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    0.1611    2.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0834    2.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741    0.6539    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823    0.7803    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -1.7060   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543   -1.5190    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879   -1.0850   -1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078    0.2230   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2858    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    1.5370    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0696    2.0687   -0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5502    2.3167   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.7350   -2.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    1.1987   -2.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224   -0.4806   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.4476   -2.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665    0.5898   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5531   -2.4371    1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972   -1.6497    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1404    0.0337    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
M  END


  Mrv0541 02241218312D          

 22 22  0  0  0  0            999 V2000
    4.6429    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2133    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2133   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2133   -1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281   -2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.8247    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  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
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038457

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)

> <INCHI_KEY>
XJQPQKLURWNAAH-UHFFFAOYSA-N

> <FORMULA>
C18H29NO3

> <MOLECULAR_WEIGHT>
307.4278

> <EXACT_MASS>
307.214743799

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.54705180199187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.111591201

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.98481071509475

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.92869178304735

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5190927904790027

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
89.2008

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrocapsaicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038457
     RDKit          3D
Dihydrocapsaicin
 51 51  0  0  0  0  0  0  0  0999 V2000
   -5.8258    2.6380   -1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1847    1.9095   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7734    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    0.2830   -0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.8576   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5811   -1.4094   -0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -1.9597   -0.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -1.0706    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    0.1679    0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -1.6682    1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617   -0.6424    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.0492    1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176   -0.9755    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507   -0.3060   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5823    0.7120   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3744    1.2988   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4028    1.9299   -2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    0.1939   -1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -1.5483    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1401   -1.0779    1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183    0.0662    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8652    0.5280    2.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    3.6762   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1843    2.1125   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7301    2.7567   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.8159   -1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -2.2419   -1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.6585   -1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -2.9804    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -2.5211    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -2.1690    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    0.1611    2.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0834    2.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741    0.6539    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823    0.7803    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -1.7060   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543   -1.5190    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879   -1.0850   -1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078    0.2230   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2858    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    1.5370    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0696    2.0687   -0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5502    2.3167   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.7350   -2.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    1.1987   -2.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224   -0.4806   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.4476   -2.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665    0.5898   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5531   -2.4371    1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972   -1.6497    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1404    0.0337    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.667   3.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.335   3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.001   3.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.335   1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.666   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.335   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.000   1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.668   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.666   1.539   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.666   3.079   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -2.000   0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.332   1.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.666   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.998   1.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.332   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.332  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.998  -1.539   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.666  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.998  -3.079   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.332  -3.849   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.667  -1.539   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   14   18                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0038457
HETATM    1  C1  UNL     1      -5.826   2.638  -1.274  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.185   1.909  -0.116  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.457   0.773   0.189  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.409   0.283  -0.541  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.713  -0.858  -0.193  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.581  -1.409  -0.977  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.606  -1.960  -0.057  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.735  -1.071   0.661  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.807   0.168   0.504  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.244  -1.668   1.589  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.162  -0.642   2.146  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.979   0.049   1.095  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.818  -0.975   0.367  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.651  -0.306  -0.693  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.582   0.712  -0.104  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.374   1.299  -1.290  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.403   1.930  -2.252  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.187   0.194  -1.889  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.088  -1.548   0.953  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.140  -1.078   1.708  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.818   0.066   1.336  1.00  0.00           C  
HETATM   22  O3  UNL     1      -6.865   0.528   2.093  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.232   3.676  -1.231  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.184   2.113  -2.204  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.730   2.757  -1.399  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.115   0.816  -1.430  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.954  -2.242  -1.645  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.178  -0.659  -1.668  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.536  -2.980   0.082  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.780  -2.521   1.099  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.292  -2.169   2.457  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.601   0.161   2.714  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.877  -1.083   2.894  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.374   0.654   0.396  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.682   0.780   1.622  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.101  -1.706  -0.106  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.454  -1.519   1.068  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.188  -1.085  -1.268  1.00  0.00           H  
HETATM   39  H17 UNL     1       3.008   0.223  -1.445  1.00  0.00           H  
HETATM   40  H18 UNL     1       5.323   0.286   0.582  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.057   1.537   0.407  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.070   2.069  -0.900  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.550   2.317  -1.661  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.896   2.735  -2.850  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.991   1.199  -2.984  1.00  0.00           H  
HETATM   46  H24 UNL     1       6.522  -0.481  -1.075  1.00  0.00           H  
HETATM   47  H25 UNL     1       5.601  -0.448  -2.589  1.00  0.00           H  
HETATM   48  H26 UNL     1       7.066   0.590  -2.443  1.00  0.00           H  
HETATM   49  H27 UNL     1      -3.553  -2.437   1.233  1.00  0.00           H  
HETATM   50  H28 UNL     1      -5.397  -1.650   2.594  1.00  0.00           H  
HETATM   51  H29 UNL     1      -7.140   0.034   2.922  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   19   19
CONECT    6    7   27   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   17   18   42
CONECT   17   43   44   45
CONECT   18   46   47   48
CONECT   19   20   49
CONECT   20   21   21   50
CONECT   21   22
CONECT   22   51
END

HMDB0038457
     RDKit          3D
Dihydrocapsaicin
 51 51  0  0  0  0  0  0  0  0999 V2000
   -5.8258    2.6380   -1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1847    1.9095   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7734    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    0.2830   -0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.8576   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5811   -1.4094   -0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -1.9597   -0.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -1.0706    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    0.1679    0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -1.6682    1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617   -0.6424    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.0492    1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176   -0.9755    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507   -0.3060   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5823    0.7120   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3744    1.2988   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4028    1.9299   -2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1874    0.1939   -1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -1.5483    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1401   -1.0779    1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183    0.0662    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8652    0.5280    2.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    3.6762   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1843    2.1125   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7301    2.7567   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.8159   -1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -2.2419   -1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.6585   -1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -2.9804    0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -2.5211    1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -2.1690    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    0.1611    2.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0834    2.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741    0.6539    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823    0.7803    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -1.7060   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543   -1.5190    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879   -1.0850   -1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078    0.2230   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2858    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    1.5370    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0696    2.0687   -0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5502    2.3167   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    2.7350   -2.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    1.1987   -2.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224   -0.4806   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.4476   -2.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665    0.5898   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5531   -2.4371    1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972   -1.6497    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1404    0.0337    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-Dihydrocapsaicin	ChEBI
8-Methyl-N-vanillylnonanamide	ChEBI
8-Methyl dihydrocapsaicin	HMDB
8-Methyl-N-vanillyl-nonanamide	HMDB
Dihydrocapsacine	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-nonanamide	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamide	HMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnonanamide	HMDB

Chemical Formula

C₁₈H₂₉NO₃

Average Molecular Weight

307.4278

Monoisotopic Molecular Weight

307.214743799

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide

Traditional Name

dihydrocapsaicin

CAS Registry Number

19408-84-5

SMILES

COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1

InChI Identifier

InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)

InChI Key

XJQPQKLURWNAAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Carboximidic acid
Carboximidic acid derivative
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

capsaicinoid (CHEBI:46932 )
Capsaicinoids and derivatives (C16952 )
N-acyl amines (LMFA08020085 )
an alkaloid (CPD-9185 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038457)

Source

Endogenous

Endogenous (HMDB: HMDB0038457)

Plant

Plant (HMDB: HMDB0038457)

Exogenous

Food

Food (HMDB: HMDB0038457)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Exogenous (HMDB: HMDB0038457)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0038457)

Role

Biological role

Energy source (HMDB: HMDB0038457)
Hypocholesterolemic (HMDB: HMDB0038457)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038457)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65.5 - 65.8 °C	Not Available
Boiling Point	497.00 to 498.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.81 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.556 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.56	ALOGPS
logP	4.11	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	89.2 m³·mol⁻¹	ChemAxon
Polarizability	36.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.786	31661259
DarkChem	[M-H]-	174.618	31661259
DeepCCS	[M+H]+	188.605	30932474
DeepCCS	[M-H]-	186.247	30932474
DeepCCS	[M-2H]-	219.134	30932474
DeepCCS	[M+Na]+	194.698	30932474
AllCCS	[M+H]+	178.2	32859911
AllCCS	[M+H-H2O]+	175.2	32859911
AllCCS	[M+NH4]+	180.8	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	179.6	32859911
AllCCS	[M+HCOO]-	180.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.33 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7732 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2625.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	314.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	778.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	672.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1515.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	555.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1510.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	254.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	194.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocapsaicin	COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1	3626.3	Standard polar	33892256
Dihydrocapsaicin	COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1	2493.9	Standard non polar	33892256
Dihydrocapsaicin	COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1	2595.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocapsaicin,1TMS,isomer #1	COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O[Si](C)(C)C	2675.7	Semi standard non polar	33892256
Dihydrocapsaicin,1TMS,isomer #2	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C)=CC=C1O	2510.9	Semi standard non polar	33892256
Dihydrocapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2572.4	Semi standard non polar	33892256
Dihydrocapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2531.2	Standard non polar	33892256
Dihydrocapsaicin,1TBDMS,isomer #1	COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2921.1	Semi standard non polar	33892256
Dihydrocapsaicin,1TBDMS,isomer #2	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2751.8	Semi standard non polar	33892256
Dihydrocapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3062.0	Semi standard non polar	33892256
Dihydrocapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2919.6	Standard non polar	33892256

Spectra

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Dihydrocapsaicin

METLIN ID

Not Available

PubChem Compound

107982

PDB ID

Not Available

ChEBI ID

46932

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1381461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Dihydrocapsaicin (HMDB0038457)

MOL for HMDB0038457 (Dihydrocapsaicin)

3D MOL for HMDB0038457 (Dihydrocapsaicin)

3D SDF for HMDB0038457 (Dihydrocapsaicin)

3D-SDF for HMDB0038457 (Dihydrocapsaicin)

PDB for HMDB0038457 (Dihydrocapsaicin)

3D PDB for HMDB0038457 (Dihydrocapsaicin)

SMILES for HMDB0038457 (Dihydrocapsaicin)

INCHI for HMDB0038457 (Dihydrocapsaicin)

Structure for HMDB0038457 (Dihydrocapsaicin)

3D Structure for HMDB0038457 (Dihydrocapsaicin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized