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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:27:38 UTC

Update Date

2022-03-07 02:54:52 UTC

HMDB ID

HMDB0036328

Secondary Accession Numbers

HMDB36328

Metabolite Identification

Common Name

Nordihydrocapsaicin

Description

Nordihydrocapsaicin 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. Thus, nordihydrocapsaicin is considered to be a fatty amide. Nordihydrocapsaicin is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), and peppers (Capsicum annuum) and in a lower concentration in orange bell peppers (Capsicum annuum), green bell peppers (Capsicum annuum), and pepper (c. frutescens). Nordihydrocapsaicin has also been detected, but not quantified in, herbs and spices and italian sweet red peppers (Capsicum annuum). This could make nordihydrocapsaicin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nordihydrocapsaicin.

Structure

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

HMDB0036328
     RDKit          3D
Nordihydrocapsaicin
 48 48  0  0  0  0  0  0  0  0999 V2000
    1.7298   -1.7625   -3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -2.2210   -2.5444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -1.3238   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880    0.0433   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.9043   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492    2.3600   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927    2.7822   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019    2.5377   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    1.9381   -1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0818    2.9792    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022    2.5982   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517    1.1064   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    0.5435    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -0.9817    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269   -1.4523    2.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942   -1.1034    2.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421   -2.9780    2.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.4508    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3789   -0.9228    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0527   -1.8186   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -3.1904   -0.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4708   -1.0726   -4.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.6040   -4.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984   -1.1406   -3.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994    0.3249   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.9057   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4468    2.5554   -2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    3.2791    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    4.1074    0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198    2.6356    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6379    3.1039   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.9355    0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362    0.8072   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    0.7008   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    0.9183    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.7108    1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -1.4482    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -1.1767    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -1.0313    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -0.1117    3.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -1.2188    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -1.8457    3.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.4189    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -3.3245    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783   -3.2583    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931    1.0892    1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -1.3289    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.5831    0.6404 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
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 18 46  1  0
 19 47  1  0
 21 48  1  0
M  END


  Mrv0541 02241216392D          

 21 21  0  0  0  0            999 V2000
   -3.9295    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    1.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429    0.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742   -0.6179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295    1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -1.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036328

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)

> <INCHI_KEY>
VQEONGKQWIFHMN-UHFFFAOYSA-N

> <FORMULA>
C17H27NO3

> <MOLECULAR_WEIGHT>
293.4012

> <EXACT_MASS>
293.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35478058183505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.667022536

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.951998651026233

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.92869169291128

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5190928434197922

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
84.59979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nordihydrocapsaicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036328
     RDKit          3D
Nordihydrocapsaicin
 48 48  0  0  0  0  0  0  0  0999 V2000
    1.7298   -1.7625   -3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -2.2210   -2.5444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -1.3238   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880    0.0433   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.9043   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492    2.3600   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927    2.7822   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019    2.5377   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    1.9381   -1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0818    2.9792    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022    2.5982   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517    1.1064   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    0.5435    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -0.9817    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269   -1.4523    2.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942   -1.1034    2.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421   -2.9780    2.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.4508    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3789   -0.9228    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0527   -1.8186   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -3.1904   -0.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4708   -1.0726   -4.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.6040   -4.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984   -1.1406   -3.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994    0.3249   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.9057   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4468    2.5554   -2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    3.2791    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    4.1074    0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198    2.6356    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6379    3.1039   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.9355    0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362    0.8072   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    0.7008   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    0.9183    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.7108    1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -1.4482    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -1.1767    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -1.0313    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -0.1117    3.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -1.2188    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -1.8457    3.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.4189    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -3.3245    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783   -3.2583    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931    1.0892    1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -1.3289    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.5831    0.6404 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
 15 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
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 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
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 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  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      -7.335   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.335  -1.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.003  -1.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.674  -1.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.674   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.003   1.153   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.003   2.693   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.667   1.153   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.340  -1.923   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.005  -1.153   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -7.335   3.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.673  -1.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.661  -1.153   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.673  -3.463   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.995  -1.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.329  -1.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.664  -1.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.998  -1.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.332  -1.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.667  -1.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.332  -3.463   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6   11                                                       
CONECT    8    1                                                            
CONECT    9    4   10                                                       
CONECT   10    9   12                                                       
CONECT   11    7                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0036328
HETATM    1  C1  UNL     1       1.730  -1.763  -3.762  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.233  -2.221  -2.544  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.559  -1.324  -1.553  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.388   0.043  -1.762  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.722   0.904  -0.757  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.549   2.360  -0.940  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.393   2.782  -0.203  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.102   2.538  -0.692  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.003   1.938  -1.799  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.082   2.979   0.086  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.402   2.598  -0.473  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.552   1.106  -0.554  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.418   0.544   0.854  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.573  -0.982   0.831  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.427  -1.452   2.255  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.094  -1.103   2.865  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.542  -2.978   2.284  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.218   0.451   0.440  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.379  -0.923   0.622  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.053  -1.819  -0.368  1.00  0.00           C  
HETATM   21  O3  UNL     1       3.201  -3.190  -0.219  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.471  -1.073  -4.235  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.476  -2.604  -4.444  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.798  -1.141  -3.639  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.999   0.325  -2.722  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.450   2.906  -0.564  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.447   2.555  -2.027  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.506   3.279   0.712  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.044   4.107   0.115  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.920   2.636   1.129  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.638   3.104  -1.434  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.232   2.935   0.222  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.536   0.807  -0.988  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.783   0.701  -1.229  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.236   0.918   1.498  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.408   0.711   1.217  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.827  -1.448   0.189  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.613  -1.177   0.525  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.213  -1.031   2.909  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.095  -0.112   3.361  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.247  -1.219   2.178  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.925  -1.846   3.692  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.519  -3.419   2.230  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.195  -3.324   1.472  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.978  -3.258   3.268  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.493   1.089   1.256  1.00  0.00           H  
HETATM   47  H26 UNL     1       3.770  -1.329   1.560  1.00  0.00           H  
HETATM   48  H27 UNL     1       3.561  -3.583   0.640  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7   26   27
CONECT    7    8   28
CONECT    8    9    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   17   39
CONECT   16   40   41   42
CONECT   17   43   44   45
CONECT   18   19   46
CONECT   19   20   20   47
CONECT   20   21
CONECT   21   48
END

HMDB0036328
     RDKit          3D
Nordihydrocapsaicin
 48 48  0  0  0  0  0  0  0  0999 V2000
    1.7298   -1.7625   -3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -2.2210   -2.5444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -1.3238   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880    0.0433   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.9043   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492    2.3600   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927    2.7822   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019    2.5377   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    1.9381   -1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0818    2.9792    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022    2.5982   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517    1.1064   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    0.5435    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -0.9817    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269   -1.4523    2.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942   -1.1034    2.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421   -2.9780    2.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.4508    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3789   -0.9228    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0527   -1.8186   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -3.1904   -0.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4708   -1.0726   -4.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.6040   -4.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984   -1.1406   -3.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994    0.3249   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.9057   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4468    2.5554   -2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    3.2791    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    4.1074    0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198    2.6356    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6379    3.1039   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.9355    0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362    0.8072   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    0.7008   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    0.9183    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.7108    1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -1.4482    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -1.1767    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -1.0313    2.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -0.1117    3.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -1.2188    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -1.8457    3.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.4189    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -3.3245    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783   -3.2583    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931    1.0892    1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -1.3289    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.5831    0.6404 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
 15 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-((4-H Ydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamide	Kegg
7-Methyl nordihydrocapsaicin	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide, 9ci	HMDB
Nordihydrocapsacin	HMDB

Chemical Formula

C₁₇H₂₇NO₃

Average Molecular Weight

293.4012

Monoisotopic Molecular Weight

293.199093735

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide

Traditional Name

nordihydrocapsaicin

CAS Registry Number

28789-35-7

SMILES

COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O

InChI Identifier

InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)

InChI Key

VQEONGKQWIFHMN-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
Fatty acyl
Fatty amide
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

an alkaloid (CPD-9182 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036328)

Cellular substructure

Extracellular (HMDB: HMDB0036328)
Membrane (HMDB: HMDB0036328)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036328)

Source

Endogenous

Endogenous (HMDB: HMDB0036328)

Plant

Plant (HMDB: HMDB0036328)

Exogenous

Food

Food (HMDB: HMDB0036328)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036328)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036328)

Nutrient

Nutrient (HMDB: HMDB0036328)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036328)

Emulsifier (HMDB: HMDB0036328)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 61 °C	Not Available
Boiling Point	486.00 to 187.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	8.92 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.046 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	3.85	ALOGPS
logP	3.67	ChemAxon
logS	-4	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	9	ChemAxon
Refractivity	84.6 m³·mol⁻¹	ChemAxon
Polarizability	34.35 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]+	172.201	31661259
DarkChem	[M-H]-	169.593	31661259
DeepCCS	[M+H]+	174.318	30932474
DeepCCS	[M-H]-	171.961	30932474
DeepCCS	[M-2H]-	205.379	30932474
DeepCCS	[M+Na]+	180.73	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.6	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	176.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nordihydrocapsaicin	COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O	3526.8	Standard polar	33892256
Nordihydrocapsaicin	COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O	2395.9	Standard non polar	33892256
Nordihydrocapsaicin	COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O	2489.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nordihydrocapsaicin,1TMS,isomer #1	COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O[Si](C)(C)C	2570.6	Semi standard non polar	33892256
Nordihydrocapsaicin,1TMS,isomer #2	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O	2412.3	Semi standard non polar	33892256
Nordihydrocapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2475.6	Semi standard non polar	33892256
Nordihydrocapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2446.1	Standard non polar	33892256
Nordihydrocapsaicin,1TBDMS,isomer #1	COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2819.1	Semi standard non polar	33892256
Nordihydrocapsaicin,1TBDMS,isomer #2	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2650.6	Semi standard non polar	33892256
Nordihydrocapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2962.5	Semi standard non polar	33892256
Nordihydrocapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2846.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocapsaicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9640000000-3871bb96b69d2739de97	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocapsaicin GC-MS (1 TMS) - 70eV, Positive	splash10-0f6x-9343000000-f1cfb2ff65932798e65a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocapsaicin 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 - Nordihydrocapsaicin 10V, Positive-QTOF	splash10-0udi-0930000000-60430aef9c68c490ba73	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Positive-QTOF	splash10-0udi-0900000000-385b7852c874b3cdd611	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Positive-QTOF	splash10-052r-4900000000-259a3bed23b06b519d14	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Negative-QTOF	splash10-0006-0390000000-8c0c3a713f8fd8b81d33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Negative-QTOF	splash10-006x-0950000000-c619e8fddd2c823a8eb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Negative-QTOF	splash10-0006-7900000000-d570a865813f7e0704f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Positive-QTOF	splash10-000i-0920000000-97edc9bdd81feca705bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Positive-QTOF	splash10-000i-1900000000-851a3e10d3faf2609c27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Positive-QTOF	splash10-000i-3900000000-63974c1e31c3ed3abbab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Negative-QTOF	splash10-0a4i-0900000000-88603c67cdd1dc1ce3e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Negative-QTOF	splash10-052o-6900000000-118ac3f38f60cd33e205	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Negative-QTOF	splash10-0006-9300000000-19b6d44cfd12492a0a03	2021-09-23	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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nordihydrocapsaicin

METLIN ID

Not Available

PubChem Compound

168836

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1381471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Nordihydrocapsaicin (HMDB0036328)

MOL for HMDB0036328 (Nordihydrocapsaicin)

3D MOL for HMDB0036328 (Nordihydrocapsaicin)

3D SDF for HMDB0036328 (Nordihydrocapsaicin)

3D-SDF for HMDB0036328 (Nordihydrocapsaicin)

PDB for HMDB0036328 (Nordihydrocapsaicin)

3D PDB for HMDB0036328 (Nordihydrocapsaicin)

SMILES for HMDB0036328 (Nordihydrocapsaicin)

INCHI for HMDB0036328 (Nordihydrocapsaicin)

Structure for HMDB0036328 (Nordihydrocapsaicin)

3D Structure for HMDB0036328 (Nordihydrocapsaicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra