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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:27:28 UTC

Update Date

2022-03-07 02:54:52 UTC

HMDB ID

HMDB0036325

Secondary Accession Numbers

HMDB36325

Metabolite Identification

Common Name

Dinorcapsaicin

Description

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

Structure

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

HMDB0036325
     RDKit          3D
Dinorcapsaicin
 43 43  0  0  0  0  0  0  0  0999 V2000
    7.1262    0.5588   -0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4987   -0.3782    0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -0.5452    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480    0.2019   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.0092   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.8154   -1.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.5079   -1.6118 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.9888   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722    1.6877    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.6659   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    1.2636    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4604    0.9667    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1340    0.2496    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598   -0.0755    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487    0.5209    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6886   -1.5964    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800   -0.9170    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.6609    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5477   -1.4640    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501   -2.2050    1.6832 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183    0.4211   -0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7692    0.4873   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9228    1.6094   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638    0.9379   -1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297    1.9032   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    0.6961   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850   -0.0602   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814    1.0942   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -0.4378   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.3533    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4544    0.8476    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332    1.3252    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.1269   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.2467   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678    1.6261    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9483    0.1014    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3504    0.3071    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643   -2.0345   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7620   -1.8790    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -2.0542    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -1.0539    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.3737    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -2.8786    2.3008 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  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
M  END


  Mrv0541 02241219392D          

 20 20  0  0  0  0            999 V2000
   -3.5729    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5729   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    1.4431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2867    0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.6181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5743    1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4266   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867   -1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717    0.2069    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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036325

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO3/c1-12(2)6-4-5-7-16(19)17-11-13-8-9-14(18)15(10-13)20-3/h4,6,8-10,12,18H,5,7,11H2,1-3H3,(H,17,19)/b6-4+

> <INCHI_KEY>
UTTHCQMKBGTYNK-GQCTYLIASA-N

> <FORMULA>
C16H23NO3

> <MOLECULAR_WEIGHT>
277.3587

> <EXACT_MASS>
277.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.459265130615723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylhept-4-enamide

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.8605322143333334

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.872438043879242

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.928691474558368

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6750809278225222

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
81.1154

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylhept-4-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036325
     RDKit          3D
Dinorcapsaicin
 43 43  0  0  0  0  0  0  0  0999 V2000
    7.1262    0.5588   -0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4987   -0.3782    0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -0.5452    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480    0.2019   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.0092   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.8154   -1.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.5079   -1.6118 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.9888   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722    1.6877    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.6659   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    1.2636    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4604    0.9667    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1340    0.2496    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598   -0.0755    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487    0.5209    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6886   -1.5964    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800   -0.9170    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.6609    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5477   -1.4640    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501   -2.2050    1.6832 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183    0.4211   -0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7692    0.4873   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9228    1.6094   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638    0.9379   -1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297    1.9032   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    0.6961   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850   -0.0602   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814    1.0942   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -0.4378   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.3533    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4544    0.8476    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332    1.3252    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.1269   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.2467   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678    1.6261    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9483    0.1014    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3504    0.3071    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643   -2.0345   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7620   -1.8790    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -2.0542    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -1.0539    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.3737    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -2.8786    2.3008 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  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  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      -6.669   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.669  -1.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.337  -1.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.008  -1.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.008   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.337   1.154   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.337   2.694   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.002   1.156   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.673  -1.924   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.338  -1.154   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -6.672   3.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.007  -1.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.328  -1.154   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.007  -3.464   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.663  -1.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.998  -1.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.332  -1.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.667  -1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -1.924   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.667   0.386   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0036325
HETATM    1  C1  UNL     1       7.126   0.559  -0.835  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.499  -0.378   0.015  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.137  -0.545   0.008  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.348   0.202  -0.834  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.964   0.009  -0.819  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.145   0.815  -1.724  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.744   0.508  -1.612  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.016   0.989  -0.508  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.572   1.688   0.391  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.430   0.666  -0.403  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.009   1.264   0.842  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.460   0.967   0.991  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.134   0.250   0.099  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.560  -0.075   0.191  1.00  0.00           C  
HETATM   15  C12 UNL     1      -6.249   0.521   1.374  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.689  -1.596   0.226  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.380  -0.917   0.026  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.182  -1.661   0.867  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.548  -1.464   0.845  1.00  0.00           C  
HETATM   20  O3  UNL     1       5.350  -2.205   1.683  1.00  0.00           O  
HETATM   21  H1  UNL     1       8.218   0.421  -0.778  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.769   0.487  -1.889  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.923   1.609  -0.498  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.764   0.938  -1.512  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.330   1.903  -1.522  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.455   0.696  -2.803  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.285  -0.060  -2.338  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.981   1.094  -1.270  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.603  -0.438  -0.438  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.847   2.353   0.841  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.454   0.848   1.727  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.033   1.325   1.839  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.590  -0.127  -0.768  1.00  0.00           H  
HETATM   34  H14 UNL     1      -6.050   0.247  -0.744  1.00  0.00           H  
HETATM   35  H15 UNL     1      -6.168   1.626   1.302  1.00  0.00           H  
HETATM   36  H16 UNL     1      -5.948   0.101   2.333  1.00  0.00           H  
HETATM   37  H17 UNL     1      -7.350   0.307   1.259  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.264  -2.034  -0.713  1.00  0.00           H  
HETATM   39  H19 UNL     1      -6.762  -1.879   0.240  1.00  0.00           H  
HETATM   40  H20 UNL     1      -5.154  -2.054   1.064  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.296  -1.054   0.024  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.745  -2.374   1.518  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.942  -2.879   2.301  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   24
CONECT    5    6   17   17
CONECT    6    7   25   26
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   16   34
CONECT   15   35   36   37
CONECT   16   38   39   40
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20
CONECT   20   43
END

HMDB0036325
     RDKit          3D
Dinorcapsaicin
 43 43  0  0  0  0  0  0  0  0999 V2000
    7.1262    0.5588   -0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4987   -0.3782    0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -0.5452    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480    0.2019   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.0092   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.8154   -1.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.5079   -1.6118 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.9888   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722    1.6877    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.6659   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    1.2636    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4604    0.9667    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1340    0.2496    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598   -0.0755    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487    0.5209    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6886   -1.5964    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800   -0.9170    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.6609    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5477   -1.4640    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3501   -2.2050    1.6832 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183    0.4211   -0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7692    0.4873   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9228    1.6094   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638    0.9379   -1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297    1.9032   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    0.6961   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850   -0.0602   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814    1.0942   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -0.4378   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.3533    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4544    0.8476    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332    1.3252    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.1269   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    0.2467   -0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678    1.6261    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9483    0.1014    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3504    0.3071    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643   -2.0345   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7620   -1.8790    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -2.0542    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -1.0539    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.3737    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -2.8786    2.3008 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  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-6-methyl-4-heptenamide	HMDB
Nornorcapsaicin	HMDB
(4E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-6-methylhept-4-enimidate	Generator

Chemical Formula

C₁₆H₂₃NO₃

Average Molecular Weight

277.3587

Monoisotopic Molecular Weight

277.167793607

IUPAC Name

(4E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylhept-4-enamide

Traditional Name

(4E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylhept-4-enamide

CAS Registry Number

61229-09-2

SMILES

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

InChI Identifier

InChI=1S/C16H23NO3/c1-12(2)6-4-5-7-16(19)17-11-13-8-9-14(18)15(10-13)20-3/h4,6,8-10,12,18H,5,7,11H2,1-3H3,(H,17,19)/b6-4+

InChI Key

UTTHCQMKBGTYNK-GQCTYLIASA-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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036325)

Source

Endogenous

Endogenous (HMDB: HMDB0036325)

Plant

Plant (HMDB: HMDB0036325)

Exogenous

Food

Food (HMDB: HMDB0036325)

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)

Exogenous (HMDB: HMDB0036325)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036325)

Role

Biological role

Energy source (HMDB: HMDB0036325)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036325)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	44.21 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	0.032 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.86	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.68	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	7	ChemAxon
Refractivity	81.12 m³·mol⁻¹	ChemAxon
Polarizability	31.46 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]+	167.159	31661259
DarkChem	[M-H]-	167.452	31661259
DeepCCS	[M+H]+	169.537	30932474
DeepCCS	[M-H]-	167.179	30932474
DeepCCS	[M-2H]-	200.302	30932474
DeepCCS	[M+Na]+	175.63	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	172.2	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.	6.76 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5466 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2290.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	250.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	589.2 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	424.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1167.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.3 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	1189.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	241.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	151.4 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
Dinorcapsaicin	COC1=CC(CNC(=O)CC\C=C\C(C)C)=CC=C1O	3471.8	Standard polar	33892256
Dinorcapsaicin	COC1=CC(CNC(=O)CC\C=C\C(C)C)=CC=C1O	2302.0	Standard non polar	33892256
Dinorcapsaicin	COC1=CC(CNC(=O)CC\C=C\C(C)C)=CC=C1O	2350.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dinorcapsaicin,1TMS,isomer #1	COC1=CC(CNC(=O)CC/C=C/C(C)C)=CC=C1O[Si](C)(C)C	2431.4	Semi standard non polar	33892256
Dinorcapsaicin,1TMS,isomer #2	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O	2326.3	Semi standard non polar	33892256
Dinorcapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2362.4	Semi standard non polar	33892256
Dinorcapsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2363.1	Standard non polar	33892256
Dinorcapsaicin,1TBDMS,isomer #1	COC1=CC(CNC(=O)CC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2673.1	Semi standard non polar	33892256
Dinorcapsaicin,1TBDMS,isomer #2	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2568.3	Semi standard non polar	33892256
Dinorcapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2829.9	Semi standard non polar	33892256
Dinorcapsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2780.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dinorcapsaicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9740000000-4a1934598645be75ee2a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dinorcapsaicin GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9234000000-48ec467cd8a974d1c8a0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dinorcapsaicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dinorcapsaicin 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 - Dinorcapsaicin 10V, Positive-QTOF	splash10-0udi-0940000000-366485dfac8d00531324	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 20V, Positive-QTOF	splash10-0udi-0900000000-be494cca8679a4f16316	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 40V, Positive-QTOF	splash10-000i-4900000000-f5fdfb549e1cfe5d90f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 10V, Negative-QTOF	splash10-004i-0390000000-2d0a405f6df662bdb58c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 20V, Negative-QTOF	splash10-004i-1950000000-c4beec27819ab04f93c9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 40V, Negative-QTOF	splash10-0006-9800000000-67d5e26908dcb0ede4ef	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 10V, Positive-QTOF	splash10-000i-0920000000-16392e4702b19a9ad8af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 20V, Positive-QTOF	splash10-000i-1900000000-cc6d73a4014e3c7291bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 40V, Positive-QTOF	splash10-000i-4900000000-948b4e80aa2317e99471	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 10V, Negative-QTOF	splash10-0006-0900000000-9c5abbde279052c9524c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 20V, Negative-QTOF	splash10-0006-7900000000-53d8e68e549d4b8ec0a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dinorcapsaicin 40V, Negative-QTOF	splash10-0006-9300000000-152a68d25a6821a2698a	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

Not Available

FooDB ID

FDB015196

KNApSAcK ID

C00057469

Chemspider ID

4946648

KEGG Compound ID

Not Available

BioCyc ID

CPD-9330

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442578

PDB ID

Not Available

ChEBI ID

172515

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1854601

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 Dinorcapsaicin (HMDB0036325)

MOL for HMDB0036325 (Dinorcapsaicin)

3D MOL for HMDB0036325 (Dinorcapsaicin)

3D SDF for HMDB0036325 (Dinorcapsaicin)

3D-SDF for HMDB0036325 (Dinorcapsaicin)

PDB for HMDB0036325 (Dinorcapsaicin)

3D PDB for HMDB0036325 (Dinorcapsaicin)

SMILES for HMDB0036325 (Dinorcapsaicin)

INCHI for HMDB0036325 (Dinorcapsaicin)

Structure for HMDB0036325 (Dinorcapsaicin)

3D Structure for HMDB0036325 (Dinorcapsaicin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra