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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:40 UTC

Update Date

2022-03-07 02:53:17 UTC

HMDB ID

HMDB0032240

Secondary Accession Numbers

HMDB32240

Metabolite Identification

Common Name

N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide

Description

N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide, also known as fema 4267 (e form), belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide.

Structure

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

HMDB0032240
     RDKit          3D
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -3.8064    1.5445    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    0.3848    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0715    0.5454    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836   -0.7574    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -0.8855    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8990   -1.2317   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -1.3888   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -2.4093    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.6235   -1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8484   -0.7842   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213    0.4064   -0.8812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    0.4050   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271   -0.6117   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983    1.6110   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    1.7602   -0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.3230    0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    2.4569    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    1.7704    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    1.2909    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5290    0.4227    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2820    1.5718    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680   -0.2393   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888   -1.5812    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.7516    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.0374    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4493   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -2.2024   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -1.9384    1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -3.0004    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -3.1300   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    0.1394   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -1.6043   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -1.0160   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807    1.2497   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.5134   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5108    1.0037   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497    2.7893   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1324    2.1088    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.2703    0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 14  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

  Mrv0541 02241221482D          

 16 16  0  0  0  0            999 V2000
    0.9526    2.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053    2.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    3.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    3.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    2.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    3.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    4.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032240

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CNC(=O)C1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO/c1-11(2)5-4-6-12(3)9-10-15-14(16)13-7-8-13/h5,9,13H,4,6-8,10H2,1-3H3,(H,15,16)/b12-9+

> <INCHI_KEY>
UKNMSFRSBQONET-FMIVXFBMSA-N

> <FORMULA>
C14H23NO

> <MOLECULAR_WEIGHT>
221.3385

> <EXACT_MASS>
221.177964363

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.5465465011652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboxamide

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
2.9941443250000006

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.223955968623677

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5922269458657429

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
69.6826

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboxamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032240
     RDKit          3D
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -3.8064    1.5445    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    0.3848    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0715    0.5454    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836   -0.7574    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -0.8855    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8990   -1.2317   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -1.3888   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -2.4093    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.6235   -1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8484   -0.7842   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213    0.4064   -0.8812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    0.4050   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271   -0.6117   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983    1.6110   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    1.7602   -0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.3230    0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    2.4569    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    1.7704    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    1.2909    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5290    0.4227    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2820    1.5718    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680   -0.2393   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888   -1.5812    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.7516    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.0374    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4493   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -2.2024   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -1.9384    1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -3.0004    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -3.1300   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    0.1394   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -1.6043   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -1.0160   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807    1.2497   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.5134   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5108    1.0037   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497    2.7893   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1324    2.1088    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.2703    0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 14  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  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  O   UNK     0       1.778   3.969   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.889   3.969   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.223   3.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.557   3.969   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.557   5.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.223   6.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.890   6.279   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.224   5.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.558   6.279   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.558   7.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.224   8.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.891   8.589   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0032240
HETATM    1  C1  UNL     1      -3.806   1.545   1.171  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.604   0.385   0.675  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.072   0.545   0.488  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.984  -0.757   0.414  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.503  -0.886   0.613  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.899  -1.232  -0.704  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.427  -1.389  -0.647  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.236  -2.409   0.227  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.376  -0.623  -1.377  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.848  -0.784  -1.317  1.00  0.00           C  
HETATM   11  N1  UNL     1       2.521   0.406  -0.881  1.00  0.00           N  
HETATM   12  C11 UNL     1       3.926   0.405  -0.775  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.627  -0.612  -1.050  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.698   1.611  -0.327  1.00  0.00           C  
HETATM   15  C13 UNL     1       6.082   1.760  -0.823  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.897   1.323   0.602  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.439   2.457   1.211  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.992   1.770   0.447  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.374   1.291   2.147  1.00  0.00           H  
HETATM   20  H4  UNL     1      -6.529   0.423   1.498  1.00  0.00           H  
HETATM   21  H5  UNL     1      -6.282   1.572   0.124  1.00  0.00           H  
HETATM   22  H6  UNL     1      -6.468  -0.239  -0.212  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.589  -1.581   0.055  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.347  -1.752   1.314  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.103   0.037   1.055  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.144  -0.449  -1.425  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.356  -2.202  -1.037  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.820  -1.938   1.038  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.575  -3.000   0.745  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.834  -3.130  -0.330  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.011   0.139  -2.037  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.155  -1.604  -0.630  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.227  -1.016  -2.345  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.981   1.250  -0.650  1.00  0.00           H  
HETATM   35  H19 UNL     1       4.111   2.513  -0.080  1.00  0.00           H  
HETATM   36  H20 UNL     1       6.511   1.004  -1.501  1.00  0.00           H  
HETATM   37  H21 UNL     1       6.450   2.789  -1.018  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.132   2.109   1.363  1.00  0.00           H  
HETATM   39  H23 UNL     1       6.071   0.270   0.884  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT    9   10   31
CONECT   10   11   32   33
CONECT   11   12   34
CONECT   12   13   13   14
CONECT   14   15   16   35
CONECT   15   16   36   37
CONECT   16   38   39
END

HMDB0032240
     RDKit          3D
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -3.8064    1.5445    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    0.3848    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0715    0.5454    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836   -0.7574    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -0.8855    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8990   -1.2317   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -1.3888   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -2.4093    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -0.6235   -1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8484   -0.7842   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213    0.4064   -0.8812 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    0.4050   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271   -0.6117   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983    1.6110   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    1.7602   -0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.3230    0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394    2.4569    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    1.7704    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    1.2909    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5290    0.4227    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2820    1.5718    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680   -0.2393   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888   -1.5812    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.7516    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.0374    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4493   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -2.2024   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -1.9384    1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -3.0004    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -3.1300   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    0.1394   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -1.6043   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -1.0160   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807    1.2497   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.5134   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5108    1.0037   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497    2.7893   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1324    2.1088    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.2703    0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 14  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide	ChEBI
(e)-N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide	ChEBI
FEMA 4267 (e form)	ChEBI
N-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]cyclopropanecarboxamide	ChEBI
N-[(2E)-3,7-Dimethyl-2,6-octadienyl]cyclopropanecarboxamide	ChEBI
N-[(2Z)-3,7-Dimethylocta-2,6-dienyl]cyclopropanecarboxamide	HMDB
N-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]cyclopropanecarboximidate	Generator

Chemical Formula

C₁₄H₂₃NO

Average Molecular Weight

221.3385

Monoisotopic Molecular Weight

221.177964363

IUPAC Name

N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboxamide

Traditional Name

N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboxamide

CAS Registry Number

744251-93-2

SMILES

CC(C)=CCC\C(C)=C\CNC(=O)C1CC1

InChI Identifier

InChI=1S/C14H23NO/c1-11(2)5-4-6-12(3)9-10-15-14(16)13-7-8-13/h5,9,13H,4,6-8,10H2,1-3H3,(H,15,16)/b12-9+

InChI Key

UKNMSFRSBQONET-FMIVXFBMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Cyclopropanecarboxylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032240)

Source

Endogenous

Endogenous (HMDB: HMDB0032240)

Animal

Animal (HMDB: HMDB0032240)

Exogenous

Food

Food (HMDB: HMDB0032240)

Exogenous (HMDB: HMDB0032240)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032240)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032240)

Lipid metabolism pathway (HMDB: HMDB0032240)

Cellular process

Cell signaling (HMDB: HMDB0032240)

Biochemical process

Lipid transport (HMDB: HMDB0032240)

Role

Biological role

Energy source (HMDB: HMDB0032240)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032240)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	53.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	388.00 to 389.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.255 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	3.83	ALOGPS
logP	2.99	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	16.22	ChemAxon
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.68 m³·mol⁻¹	ChemAxon
Polarizability	27.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.839	31661259
DarkChem	[M-H]-	151.741	31661259
DeepCCS	[M+H]+	155.216	30932474
DeepCCS	[M-H]-	152.858	30932474
DeepCCS	[M-2H]-	186.734	30932474
DeepCCS	[M+Na]+	161.645	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide	CC(C)=CCC\C(C)=C\CNC(=O)C1CC1	2585.9	Standard polar	33892256
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide	CC(C)=CCC\C(C)=C\CNC(=O)C1CC1	1809.4	Standard non polar	33892256
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide	CC(C)=CCC\C(C)=C\CNC(=O)C1CC1	1835.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CN(C(=O)C1CC1)[Si](C)(C)C	1835.9	Semi standard non polar	33892256
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CN(C(=O)C1CC1)[Si](C)(C)C	1853.9	Standard non polar	33892256
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CN(C(=O)C1CC1)[Si](C)(C)C(C)(C)C	2056.7	Semi standard non polar	33892256
N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CN(C(=O)C1CC1)[Si](C)(C)C(C)(C)C	2082.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9300000000-8b6134db22152ed4fb17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 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 - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 10V, Positive-QTOF	splash10-00di-4890000000-9a9b0f09a14a5bc124b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 20V, Positive-QTOF	splash10-014r-9610000000-2cc88c42b780bc084c4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 40V, Positive-QTOF	splash10-00kf-9100000000-d4d872c9b12b5df72875	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 10V, Negative-QTOF	splash10-00di-1190000000-8fcef029e1f9b2c8c37b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 20V, Negative-QTOF	splash10-00di-9770000000-89b8b1256ed3ed4aed15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 40V, Negative-QTOF	splash10-0006-9200000000-34925186fd61da40e7d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 10V, Negative-QTOF	splash10-00di-0190000000-035fbe2146db96e545d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 20V, Negative-QTOF	splash10-00dl-9540000000-e8a520e7dfabc8a6c809	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 40V, Negative-QTOF	splash10-0006-9300000000-66697a9f4ecf9f1dd5cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 10V, Positive-QTOF	splash10-01bc-9120000000-ef2f76d44af2e27f8446	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 20V, Positive-QTOF	splash10-014i-9000000000-e7a66179b3922de5d61b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide 40V, Positive-QTOF	splash10-00kf-9000000000-115570d33c8ea120bab7	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

FDB009327

KNApSAcK ID

Not Available

Chemspider ID

9833352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11658617

PDB ID

Not Available

ChEBI ID

173636

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1593721

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide (HMDB0032240)

MOL for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

3D MOL for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

3D SDF for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

3D-SDF for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

PDB for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

3D PDB for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

SMILES for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

INCHI for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

Structure for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

3D Structure for HMDB0032240 (N-3,7-Dimethyl-2,6-octadienylcyclopropylcarboxamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra