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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:01 UTC

Update Date

2022-03-07 02:52:19 UTC

HMDB ID

HMDB0029846

Secondary Accession Numbers

HMDB29846

Metabolite Identification

Common Name

Nonivamide

Description

Nonivamide, also known as pseudocapsaicin or hansaplast, 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. Nonivamide is odorless and a bland tasting compound. Nonivamide is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (C. frutescens) and in a lower concentration in pepper (C. annuum), orange bell peppers, and green bell peppers. Nonivamide has also been detected, but not quantified, in herbs and spices. This could make nonivamide a potential biomarker for the consumption of these foods. Limited information is available on pharmacokinetics and metabolism of nonivamide. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death . The cardiovascular effects are partly explained by substance P release. Administered intraperitoneally, the LD50 in rats was measured to be about 90 mg/kg. Nonivamide has been shown to stimulate afferent neurons with about half the potency of Capsaicin (PMID:6202305 ).

Structure

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

HMDB0029846
     RDKit          3D
Nonivamide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -6.6035    1.6690    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7840    1.1777   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.1514    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9007    0.8423    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8496   -0.0874    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368   -0.6198    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2073    0.4565   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3218   -0.0869   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.9850   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -1.1945    0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.6464   -1.6781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5120   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -1.7306   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -2.3480   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -1.6417    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.2704    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445    0.5088    0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105    0.4005   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300    1.7738   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5971    2.3950   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8832   -0.6374   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105    0.7614   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.4945   -2.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -3.2054   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -3.0767   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -3.4297   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8316   -2.1707    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6799    2.1689   -0.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    2.0570   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    3.5044   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.1706   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 21 48  1  0
M  END


  Mrv1652305201900042D          

 21 21  0  0  0  0            999 V2000
   -2.8574   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5707   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5707   -1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854   -1.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5707    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2854    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  2  0  0  0  0
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 17 18  1  0  0  0  0
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 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029846

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

> <INCHI_KEY>
RGOVYLWUIBMPGK-UHFFFAOYSA-N

> <FORMULA>
C17H27NO3

> <MOLECULAR_WEIGHT>
293.4012

> <EXACT_MASS>
293.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.074806087574814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
3.8245721046666663

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.951998651090193

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.928691692897024

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4198503157728308

> <JCHEM_POLAR_SURFACE_AREA>
58.559999999999995

> <JCHEM_REFRACTIVITY>
84.65220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nonivamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029846
     RDKit          3D
Nonivamide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -6.6035    1.6690    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7840    1.1777   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.1514    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9007    0.8423    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8496   -0.0874    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368   -0.6198    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2073    0.4565   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3218   -0.0869   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.9850   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -1.1945    0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.6464   -1.6781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5120   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -1.7306   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -2.3480   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -1.6417    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.2704    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445    0.5088    0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105    0.4005   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300    1.7738   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5971    2.3950   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -0.3529   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7394    0.8874    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176    2.5633    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6374    1.9838    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4889    0.7347   -1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1972   -0.2715   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8832   -0.6374   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105    0.7614   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.4945   -2.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -3.2054   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -3.0767   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -3.4297   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8316   -2.1707    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7706    0.0656    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    2.1689   -0.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    2.0570   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    3.5044   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.1706   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  7 35  1  0
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 11 39  1  0
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 14 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0      -5.334  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.665  -1.154   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.665  -2.694   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.999  -3.463   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.666   1.154   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -4.000   1.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.334   1.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.665   1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.999   1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.999  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -9.331  -1.154   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.463   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334   1.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   1.154   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.331   1.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.665   1.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.000   1.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.331   1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.665   1.924   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.999   1.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.331   1.924   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   13                                                       
CONECT    6    5    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    5   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0029846
HETATM    1  C1  UNL     1      -6.603   1.669   0.730  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.784   1.178  -0.428  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.778   0.151   0.058  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.901   0.842   1.077  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.850  -0.087   1.637  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.937  -0.620   0.554  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.207   0.456  -0.166  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.322  -0.087  -1.231  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.756  -0.985  -0.757  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.938  -1.194   0.463  1.00  0.00           O  
HETATM   11  N1  UNL     1       1.628  -1.646  -1.678  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.664  -2.512  -1.177  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.796  -1.731  -0.627  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.909  -2.348  -0.102  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.975  -1.642   0.415  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.919  -0.270   0.403  1.00  0.00           C  
HETATM   17  O2  UNL     1       6.944   0.509   0.902  1.00  0.00           O  
HETATM   18  C15 UNL     1       4.810   0.400  -0.118  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.730   1.774  -0.141  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.597   2.395  -0.676  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.772  -0.353  -0.623  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.739   0.887   1.497  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.118   2.563   1.200  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.637   1.984   0.407  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.489   0.735  -1.163  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.261   2.028  -0.912  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.330  -0.691   0.523  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.197  -0.272  -0.783  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.434   1.747   0.682  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.554   1.139   1.926  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.224   0.519   2.325  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.270  -0.909   2.230  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.238  -1.308   1.053  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.490  -1.221  -0.195  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.562   1.041   0.526  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.938   1.144  -0.686  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.883  -0.637  -2.029  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.210   0.761  -1.754  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.504  -1.495  -2.702  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.995  -3.205  -1.976  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.222  -3.077  -0.314  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.960  -3.430  -0.090  1.00  0.00           H  
HETATM   43  H22 UNL     1       6.832  -2.171   0.818  1.00  0.00           H  
HETATM   44  H23 UNL     1       7.771   0.066   1.292  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.680   2.169  -0.073  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.430   2.057  -1.721  1.00  0.00           H  
HETATM   47  H26 UNL     1       3.787   3.504  -0.635  1.00  0.00           H  
HETATM   48  H27 UNL     1       2.916   0.171  -1.025  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   10   11
CONECT   11   12   39
CONECT   12   13   40   41
CONECT   13   14   14   21
CONECT   14   15   42
CONECT   15   16   16   43
CONECT   16   17   18
CONECT   17   44
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   45   46   47
CONECT   21   48
END

HMDB0029846
     RDKit          3D
Nonivamide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -6.6035    1.6690    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7840    1.1777   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.1514    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9007    0.8423    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8496   -0.0874    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368   -0.6198    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2073    0.4565   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3218   -0.0869   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -0.9850   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -1.1945    0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.6464   -1.6781 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5120   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -1.7306   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -2.3480   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -1.6417    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.2704    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445    0.5088    0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8105    0.4005   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300    1.7738   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5971    2.3950   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -0.3529   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7394    0.8874    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176    2.5633    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6374    1.9838    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4889    0.7347   -1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2605    2.0284   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297   -0.6908    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -0.2715   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343    1.7465    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    1.1393    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242    0.5191    2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.9095    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2377   -1.3084    1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -1.2205   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    1.0414    0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379    1.1440   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8832   -0.6374   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105    0.7614   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.4945   -2.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -3.2054   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -3.0767   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -3.4297   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8316   -2.1707    0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7706    0.0656    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    2.1689   -0.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    2.0570   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    3.5044   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.1706   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hydroxymethoxybenzyl pelargonamide	ChEBI
N-Nonanoyl vanillylamide	ChEBI
N-Vanillylnonamide	ChEBI
N-Vanillylpelargonamide	ChEBI
Pelargonyl vanillylamide	ChEBI
Pseudocapsaicin	ChEBI
Vanillyl-N-nonylamide	ChEBI
Nonanoic acid vanillylamide	Kegg
Hansaplast	Kegg
Nonanoate vanillylamide	Generator
4-Hydroxy-3-methoxy-N-(1-oxononyl)-benzamide	HMDB
FEMA 2787	HMDB
HH 50	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-nonanamide	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide	HMDB
N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide	HMDB
N-(4-Hydroxy-3-methoxybenzyl)nonanamide	HMDB
N-Vanillyl nonanamide	HMDB
N-Vanillyl-nonanamide	HMDB
N-Vanillylnonanamide, 8ci	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-nonanamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9ci	HMDB
Nonanoyl 4-hydroxy-3-methoxybenzylamide	HMDB
Nonanoyl vanillylamide	HMDB
Nonoyl vanillylamide	HMDB
Nonylic acid vanillylamide	HMDB
Nonylvanylamide	HMDB
Pelargonic acid vanillylamide	HMDB
Pelargonoyl vanillylamide	HMDB
PSVA	HMDB
Synthetic capsaicin	HMDB
Vanillyl N-nonoylamide	HMDB
Vanillyl pelargonic amide	HMDB
N-Vanillylnonanamide	MeSH
Vanillylnonanamide	MeSH

Chemical Formula

C₁₇H₂₇NO₃

Average Molecular Weight

293.4012

Monoisotopic Molecular Weight

293.199093735

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

Traditional Name

nonivamide

CAS Registry Number

2444-46-4

SMILES

CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

InChI Key

RGOVYLWUIBMPGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:46936 )
capsaicinoid (CHEBI:46936 )
an alkaloid (CPD-9183 )

Ontology

Cell membrane (HMDB: HMDB0029846)

Cellular substructure

Extracellular (HMDB: HMDB0029846)
Membrane (HMDB: HMDB0029846)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029846)

Source

Endogenous

Endogenous (HMDB: HMDB0029846)

Plant

Plant (HMDB: HMDB0029846)

Exogenous

Food

Food (HMDB: HMDB0029846)

Vegetable

Fruit vegetable

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

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0029846)

Role

Biological role

Energy source (HMDB: HMDB0029846)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029846)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029846)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0029846)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124.00 to 128.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	492.00 to 493.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.202 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	4.05	ALOGPS
logP	3.82	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	84.65 m³·mol⁻¹	ChemAxon
Polarizability	35.07 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]+	174.491	31661259
DarkChem	[M-H]-	173.478	31661259
DeepCCS	[M+H]+	179.525	30932474
DeepCCS	[M-H]-	177.167	30932474
DeepCCS	[M-2H]-	210.053	30932474
DeepCCS	[M+Na]+	185.623	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.6	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nonivamide	CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1	3683.9	Standard polar	33892256
Nonivamide	CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1	2477.3	Standard non polar	33892256
Nonivamide	CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1	2546.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nonivamide,1TMS,isomer #1	CCCCCCCCC(=O)NCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	2604.5	Semi standard non polar	33892256
Nonivamide,1TMS,isomer #2	CCCCCCCCC(=O)N(CC1=CC=C(O)C(OC)=C1)[Si](C)(C)C	2458.9	Semi standard non polar	33892256
Nonivamide,2TMS,isomer #1	CCCCCCCCC(=O)N(CC1=CC=C(O[Si](C)(C)C)C(OC)=C1)[Si](C)(C)C	2519.5	Semi standard non polar	33892256
Nonivamide,2TMS,isomer #1	CCCCCCCCC(=O)N(CC1=CC=C(O[Si](C)(C)C)C(OC)=C1)[Si](C)(C)C	2496.0	Standard non polar	33892256
Nonivamide,1TBDMS,isomer #1	CCCCCCCCC(=O)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2862.2	Semi standard non polar	33892256
Nonivamide,1TBDMS,isomer #2	CCCCCCCCC(=O)N(CC1=CC=C(O)C(OC)=C1)[Si](C)(C)C(C)(C)C	2704.0	Semi standard non polar	33892256
Nonivamide,2TBDMS,isomer #1	CCCCCCCCC(=O)N(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)[Si](C)(C)C(C)(C)C	3020.3	Semi standard non polar	33892256
Nonivamide,2TBDMS,isomer #1	CCCCCCCCC(=O)N(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)[Si](C)(C)C(C)(C)C	2896.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Nonivamide EI-B (Non-derivatized)	splash10-000i-0900000000-6f2029bbeaa0669340a0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Nonivamide EI-B (Non-derivatized)	splash10-000i-0900000000-6f2029bbeaa0669340a0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nonivamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-7920000000-cd906e25cbbe33ac1d90	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nonivamide GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-9483000000-60843c2f864991f329cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nonivamide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide , positive-QTOF	splash10-000i-3900000000-0e1c18bae04636c6203e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-8458eb835ff534a3139b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 90V, Positive-QTOF	splash10-0076-9700000000-2a59478a1e48f1fb682f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 75V, Positive-QTOF	splash10-0079-3900000000-d2e771312ae8b15c0eb8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 15V, Negative-QTOF	splash10-0a4i-0900000000-36905c7dcb78a52a01de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 30V, Negative-QTOF	splash10-0a4i-0900000000-d045e39cc84e57890cb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 60V, Positive-QTOF	splash10-000i-1900000000-9648421277a046c73ead	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 45V, Positive-QTOF	splash10-000i-0900000000-13d27fcfbe7bec731374	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 15V, Positive-QTOF	splash10-000i-0900000000-7d5ea4adf9a443e85cfa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 30V, Positive-QTOF	splash10-000i-0900000000-89b62e29d94cae157848	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 60V, Negative-QTOF	splash10-0a4i-0900000000-bea368f052fc74b2e53a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 45V, Negative-QTOF	splash10-0a4i-0900000000-831a7310ced159f2faad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nonivamide 35V, Positive-QTOF	splash10-000i-0900000000-c1069887607603f3585a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 10V, Positive-QTOF	splash10-0006-0950000000-67e561ae29f2afb29778	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 20V, Positive-QTOF	splash10-000i-1900000000-22d461bcbb8449562ea6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 40V, Positive-QTOF	splash10-000i-5900000000-0d2b494b9af632d043d1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 10V, Negative-QTOF	splash10-0006-0390000000-ec9c31843d3afbcd0939	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 20V, Negative-QTOF	splash10-0k9f-0940000000-709a4f4d48c16fcf8747	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 40V, Negative-QTOF	splash10-052o-7900000000-f49d6bc681a0fe7bb4ac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 10V, Negative-QTOF	splash10-0a4l-0940000000-5c718c68d8c665417132	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 20V, Negative-QTOF	splash10-0a4i-4900000000-326a985c62c83a12039a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 40V, Negative-QTOF	splash10-0006-9100000000-d2ec78d0636bf28260d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 10V, Positive-QTOF	splash10-000l-0950000000-d3e4a41c8ad8728aabf1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 20V, Positive-QTOF	splash10-000i-0900000000-1c17ee8d9e776e99b722	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nonivamide 40V, Positive-QTOF	splash10-000i-2900000000-1c8124772393ecc8fd3d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

DB11324

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001066

KNApSAcK ID

C00054000

Chemspider ID

2891

KEGG Compound ID

Not Available

BioCyc ID

CPD-9183

BiGG ID

Not Available

Wikipedia Link

Nonivamide

METLIN ID

Not Available

PubChem Compound

2998

PDB ID

Not Available

ChEBI ID

46936

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Skofitsch G, Donnerer J, Lembeck F: Comparison of nonivamide and capsaicin with regard to their pharmacokinetics and effects on sensory neurons. Arzneimittelforschung. 1984;34(2):154-6. [PubMed:6202305 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nonivamide (HMDB0029846)

MOL for HMDB0029846 (Nonivamide)

3D MOL for HMDB0029846 (Nonivamide)

3D SDF for HMDB0029846 (Nonivamide)

3D-SDF for HMDB0029846 (Nonivamide)

PDB for HMDB0029846 (Nonivamide)

3D PDB for HMDB0029846 (Nonivamide)

SMILES for HMDB0029846 (Nonivamide)

INCHI for HMDB0029846 (Nonivamide)

Structure for HMDB0029846 (Nonivamide)

3D Structure for HMDB0029846 (Nonivamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra