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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:27:35 UTC

Update Date

2022-03-07 02:54:52 UTC

HMDB ID

HMDB0036327

Secondary Accession Numbers

HMDB36327

Metabolite Identification

Common Name

Norcapsaicin

Description

Norcapsaicin 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. Norcapsaicin has been detected, but not quantified in, several different foods, such as yellow bell peppers (Capsicum annuum), orange bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), herbs and spices, and italian sweet red peppers (Capsicum annuum). This could make norcapsaicin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Norcapsaicin.

Structure

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

HMDB0036327
     RDKit          3D
Norcapsaicin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.2464    0.3759    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7849    0.9830    1.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.7109   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.2622   -0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.5361   -1.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -1.5302   -2.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338   -2.2106   -1.2124 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -1.5581   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -0.3938   -0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -2.2837    0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -1.4728    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.2478    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061   -0.4246    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278    0.7605    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877    1.6438    0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8592    1.7552   -0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4599    1.0242    2.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329    0.1867   -2.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797    1.1475   -2.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050    1.4203   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    2.3951   -0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.0215    3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.6198    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.2620    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -0.8194    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -1.0393   -2.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -2.2352   -2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -3.1890   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -3.2543    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645   -2.4880    1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -0.5012    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.9570    2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -0.8236   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507   -2.2684   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9472   -0.7888    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0986   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    2.6598    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    0.7237   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3892    2.3607   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7950    2.1690    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8354    0.0198    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    0.8239    2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3489    1.5870    2.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.0082   -3.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015    1.7210   -3.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3497    2.6451   -0.0299 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  2  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
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
M  END


  Mrv0541 02241215422D          

 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
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 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>
HMDB0036327

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h5,7,9-11,13,19H,4,6,8,12H2,1-3H3,(H,18,20)/b7-5+

> <INCHI_KEY>
UTNZMGHHFHHIAY-FNORWQNLSA-N

> <FORMULA>
C17H25NO3

> <MOLECULAR_WEIGHT>
291.3853

> <EXACT_MASS>
291.183443671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.76956525090891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enamide

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.3051008793333336

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.915370596053801

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.92869161395119

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5318099050261557

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
85.7164

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036327
     RDKit          3D
Norcapsaicin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.2464    0.3759    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7849    0.9830    1.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.7109   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.2622   -0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.5361   -1.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -1.5302   -2.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338   -2.2106   -1.2124 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -1.5581   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -0.3938   -0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -2.2837    0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -1.4728    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.2478    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061   -0.4246    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278    0.7605    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877    1.6438    0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8592    1.7552   -0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4599    1.0242    2.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329    0.1867   -2.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797    1.1475   -2.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050    1.4203   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    2.3951   -0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.0215    3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.6198    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.2620    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -0.8194    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -1.0393   -2.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -2.2352   -2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -3.1890   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -3.2543    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645   -2.4880    1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -0.5012    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.9570    2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -0.8236   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507   -2.2684   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9472   -0.7888    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0986   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    2.6598    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    0.7237   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3892    2.3607   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7950    2.1690    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8354    0.0198    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    0.8239    2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3489    1.5870    2.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.0082   -3.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015    1.7210   -3.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3497    2.6451   -0.0299 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  2  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
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  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    HMDB0036327
HETATM    1  C1  UNL     1       4.246   0.376   2.200  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.785   0.983   1.066  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.461   0.711  -0.238  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.502  -0.262  -0.539  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.176  -0.536  -1.840  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.189  -1.530  -2.282  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.534  -2.211  -1.212  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.517  -1.558  -0.473  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.202  -0.394  -0.763  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.142  -2.284   0.624  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.271  -1.473   1.177  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.311  -1.248   0.138  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.406  -0.425   0.782  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.728   0.760   0.303  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.788   1.644   0.865  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.859   1.755  -0.227  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.460   1.024   2.059  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.833   0.187  -2.824  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.780   1.148  -2.535  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.105   1.420  -1.226  1.00  0.00           C  
HETATM   21  O3  UNL     1       6.065   2.395  -0.948  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.456   1.021   3.086  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.654  -0.620   2.421  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.134   0.262   2.159  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.996  -0.819   0.228  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.400  -1.039  -2.921  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.711  -2.235  -2.978  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.831  -3.189  -1.003  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.575  -3.254   0.287  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.564  -2.488   1.474  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.826  -0.501   1.537  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.677  -1.957   2.092  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.995  -0.824  -0.804  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.751  -2.268  -0.089  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.947  -0.789   1.646  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.164   1.099  -0.569  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.412   2.660   1.089  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.955   0.724  -0.650  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.389   2.361  -1.038  1.00  0.00           H  
HETATM   40  H19 UNL     1      -6.795   2.169   0.145  1.00  0.00           H  
HETATM   41  H20 UNL     1      -5.835   0.020   1.722  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.767   0.824   2.892  1.00  0.00           H  
HETATM   43  H22 UNL     1      -6.349   1.587   2.372  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.611   0.008  -3.874  1.00  0.00           H  
HETATM   45  H24 UNL     1       5.301   1.721  -3.302  1.00  0.00           H  
HETATM   46  H25 UNL     1       6.350   2.645  -0.030  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   14   35
CONECT   14   15   36
CONECT   15   16   17   37
CONECT   16   38   39   40
CONECT   17   41   42   43
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21
CONECT   21   46
END

HMDB0036327
     RDKit          3D
Norcapsaicin
 46 46  0  0  0  0  0  0  0  0999 V2000
    4.2464    0.3759    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7849    0.9830    1.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.7109   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.2622   -0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.5361   -1.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -1.5302   -2.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338   -2.2106   -1.2124 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -1.5581   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -0.3938   -0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -2.2837    0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -1.4728    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.2478    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061   -0.4246    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278    0.7605    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877    1.6438    0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8592    1.7552   -0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4599    1.0242    2.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329    0.1867   -2.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797    1.1475   -2.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050    1.4203   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    2.3951   -0.9477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.0215    3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.6198    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.2620    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -0.8194    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -1.0393   -2.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -2.2352   -2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -3.1890   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -3.2543    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645   -2.4880    1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -0.5012    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.9570    2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -0.8236   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507   -2.2684   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9472   -0.7888    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    1.0986   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    2.6598    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    0.7237   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3892    2.3607   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7950    2.1690    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8354    0.0198    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    0.8239    2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3489    1.5870    2.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.0082   -3.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015    1.7210   -3.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3497    2.6451   -0.0299 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  2  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
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methyl-N-vanillyl-5-octenamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyl-5-octenamide, 9ci	HMDB
(5E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enimidate	Generator

Chemical Formula

C₁₇H₂₅NO₃

Average Molecular Weight

291.3853

Monoisotopic Molecular Weight

291.183443671

IUPAC Name

(5E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enamide

Traditional Name

(5E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enamide

CAS Registry Number

61229-08-1

SMILES

COC1=CC(CNC(=O)CCC\C=C\C(C)C)=CC=C1O

InChI Identifier

InChI=1S/C17H25NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h5,7,9-11,13,19H,4,6,8,12H2,1-3H3,(H,18,20)/b7-5+

InChI Key

UTNZMGHHFHHIAY-FNORWQNLSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036327)

Cellular substructure

Extracellular (HMDB: HMDB0036327)
Membrane (HMDB: HMDB0036327)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036327)

Source

Endogenous

Endogenous (HMDB: HMDB0036327)

Plant

Plant (HMDB: HMDB0036327)

Exogenous

Food

Food (HMDB: HMDB0036327)

Vegetable

Fruit vegetable

Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036327)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036327)

Nutrient

Nutrient (HMDB: HMDB0036327)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036327)

Emulsifier (HMDB: HMDB0036327)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	42.5 - 44 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.98 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	0.016 g/L	ALOGPS
logP	3.23	ALOGPS
logP	3.31	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.53	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	8	ChemAxon
Refractivity	85.72 m³·mol⁻¹	ChemAxon
Polarizability	33.77 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]+	173.681	31661259
DarkChem	[M-H]-	172.606	31661259
DeepCCS	[M+H]+	171.749	30932474
DeepCCS	[M-H]-	169.392	30932474
DeepCCS	[M-2H]-	202.579	30932474
DeepCCS	[M+Na]+	177.843	30932474
AllCCS	[M+H]+	172.6	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.4	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norcapsaicin	COC1=CC(CNC(=O)CCC\C=C\C(C)C)=CC=C1O	3549.2	Standard polar	33892256
Norcapsaicin	COC1=CC(CNC(=O)CCC\C=C\C(C)C)=CC=C1O	2401.5	Standard non polar	33892256
Norcapsaicin	COC1=CC(CNC(=O)CCC\C=C\C(C)C)=CC=C1O	2451.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norcapsaicin,1TMS,isomer #1	COC1=CC(CNC(=O)CCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C	2533.6	Semi standard non polar	33892256
Norcapsaicin,1TMS,isomer #2	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O	2422.1	Semi standard non polar	33892256
Norcapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2459.2	Semi standard non polar	33892256
Norcapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2446.5	Standard non polar	33892256
Norcapsaicin,1TBDMS,isomer #1	COC1=CC(CNC(=O)CCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2780.9	Semi standard non polar	33892256
Norcapsaicin,1TBDMS,isomer #2	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2652.4	Semi standard non polar	33892256
Norcapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2923.9	Semi standard non polar	33892256
Norcapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2854.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norcapsaicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-06v1-9860000000-7f0cce7a6e0d72d989be	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcapsaicin GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9354000000-13494c413e4cfc0b9b12	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcapsaicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcapsaicin 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 - Norcapsaicin 10V, Positive-QTOF	splash10-0udi-0930000000-ff89679c279bef408e56	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 20V, Positive-QTOF	splash10-0udi-0900000000-cc078b4ce78142bcaf0a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 40V, Positive-QTOF	splash10-0f79-4900000000-ddd8fee94d4995be277b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 10V, Negative-QTOF	splash10-0006-0390000000-73dd3e47fc61a298fc7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 20V, Negative-QTOF	splash10-0ukc-0950000000-2e5b6c7915e6e536768f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 40V, Negative-QTOF	splash10-0006-8900000000-67859e3cb1f23695c400	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 10V, Negative-QTOF	splash10-0udi-0910000000-611201cb2dd90b5a6dfb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 20V, Negative-QTOF	splash10-01p6-6900000000-12637374c098a05e3e9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 40V, Negative-QTOF	splash10-0006-9400000000-c6c88c14073f72ed4d9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 10V, Positive-QTOF	splash10-000i-0910000000-cb193d8139a4c83cc19e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 20V, Positive-QTOF	splash10-000i-1900000000-fbc009ceb11a4f1fb96b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcapsaicin 40V, Positive-QTOF	splash10-000i-4900000000-6df772803a1938ae3954	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

FDB015198

KNApSAcK ID

C00057468

Chemspider ID

4946647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442577

PDB ID

Not Available

ChEBI ID

174089

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1854621

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 Norcapsaicin (HMDB0036327)

MOL for HMDB0036327 (Norcapsaicin)

3D MOL for HMDB0036327 (Norcapsaicin)

3D SDF for HMDB0036327 (Norcapsaicin)

3D-SDF for HMDB0036327 (Norcapsaicin)

PDB for HMDB0036327 (Norcapsaicin)

3D PDB for HMDB0036327 (Norcapsaicin)

SMILES for HMDB0036327 (Norcapsaicin)

INCHI for HMDB0036327 (Norcapsaicin)

Structure for HMDB0036327 (Norcapsaicin)

3D Structure for HMDB0036327 (Norcapsaicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra