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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:15:55 UTC

Update Date

2022-03-07 02:53:45 UTC

HMDB ID

HMDB0033527

Secondary Accession Numbers

HMDB33527

Metabolite Identification

Common Name

Dehydroisochalciporone

Description

Dehydroisochalciporone belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Dehydroisochalciporone has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make dehydroisochalciporone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydroisochalciporone.

Structure

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

HMDB0033527
     RDKit          3D
Dehydroisochalciporone
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4030    0.6847    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653    0.3775    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -1.0429    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -1.6954    0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.9407    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -1.6173    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -0.2776    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.0362   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1746    1.2966   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    1.5931   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404    0.6670   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    1.2461   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    0.7107   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6652    1.7659   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8426   -0.4624    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0786   -1.5307    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454   -1.7362   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390   -0.7458   -0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147    1.6351   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9446   -0.1805   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172    0.6716    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.9320    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    0.7919   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -3.0469    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5652   -2.4089    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    0.5696    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.8646    0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    2.1264   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3169    2.6862   -0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    0.4111   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3523    2.7625   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.7314    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6646    1.4670   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7053   -0.4475    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -2.3239    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -2.7407   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.0282   -1.4153 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv0541 05061307102D          

 18 18  0  0  0  0            999 V2000
    5.1434    4.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434    3.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4289    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4289    3.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    3.8382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  2  0  0  0  0
 12  9  2  0  0  0  0
 13  7  2  0  0  0  0
 14  2  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033527

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)\C=C/C=C/C=C\C1=NC(C)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO/c1-3-16(18)13-7-5-4-6-11-15-12-9-8-10-14(2)17-15/h4-14H,3H2,1-2H3/b5-4+,11-6-,13-7-

> <INCHI_KEY>
WJIGOTVFVWHJRY-BYWROCKKSA-N

> <FORMULA>
C16H19NO

> <MOLECULAR_WEIGHT>
241.3282

> <EXACT_MASS>
241.146664235

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.378997800504443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,6E,8Z)-9-(2-methyl-2H-azepin-7-yl)nona-4,6,8-trien-3-one

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.934166098333333

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.396279961675967

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
82.4991

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,6E,8Z)-9-(7-methyl-7H-azepin-2-yl)nona-4,6,8-trien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033527
     RDKit          3D
Dehydroisochalciporone
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4030    0.6847    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653    0.3775    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -1.0429    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -1.6954    0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.9407    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -1.6173    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -0.2776    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.0362   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1746    1.2966   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    1.5931   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404    0.6670   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    1.2461   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    0.7107   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6652    1.7659   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8426   -0.4624    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0786   -1.5307    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454   -1.7362   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390   -0.7458   -0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147    1.6351   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9446   -0.1805   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172    0.6716    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.9320    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    0.7919   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -3.0469    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5652   -2.4089    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    0.5696    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.8646    0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    2.1264   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3169    2.6862   -0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    0.4111   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3523    2.7625   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.7314    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6646    1.4670   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7053   -0.4475    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -2.3239    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -2.7407   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.0282   -1.4153 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.601   8.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.633   0.032   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.601   7.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.266   4.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.600   4.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.934   4.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.986   1.877   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.267   4.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.267   6.395   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.211   1.877   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       6.934   7.165   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   14                                                            
CONECT    3    1   16                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8    9   10                                                       
CONECT    9    8   12                                                       
CONECT   10    8   14                                                       
CONECT   11    6   15                                                       
CONECT   12    9   15                                                       
CONECT   13    7   16                                                       
CONECT   14    2   10   17                                                  
CONECT   15   11   12   17                                                  
CONECT   16    3   13   18                                                  
CONECT   17   14   15                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0033527
HETATM    1  C1  UNL     1       6.403   0.685   0.423  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.865   0.377   0.343  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.688  -1.043   0.526  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.823  -1.695   0.730  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.592  -1.941   0.545  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.346  -1.617   0.373  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.936  -0.278   0.138  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.622  -0.036  -0.024  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.175   1.297  -0.261  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.067   1.593  -0.466  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.140   0.667  -0.512  1.00  0.00           C  
HETATM   12  N1  UNL     1      -3.323   1.246  -0.503  1.00  0.00           N  
HETATM   13  C11 UNL     1      -4.665   0.711  -0.531  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.665   1.766  -0.105  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.843  -0.462   0.337  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.079  -1.531   0.436  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.845  -1.736  -0.356  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.039  -0.746  -0.746  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.615   1.635  -0.068  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.945  -0.181  -0.012  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.617   0.672   1.508  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.395   0.932   1.190  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.604   0.792  -0.649  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.757  -3.047   0.720  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.565  -2.409   0.408  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.546   0.570   0.072  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.021  -0.865   0.117  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.934   2.126  -0.270  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.317   2.686  -0.631  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.882   0.411  -1.571  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.352   2.763  -0.450  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.726   1.731   1.005  1.00  0.00           H  
HETATM   33  H15 UNL     1      -6.665   1.467  -0.500  1.00  0.00           H  
HETATM   34  H16 UNL     1      -5.705  -0.447   0.969  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.326  -2.324   1.106  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.566  -2.741  -0.633  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.201  -1.028  -1.415  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    4    5
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   18
CONECT   12   13
CONECT   13   14   15   30
CONECT   14   31   32   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   37
END

HMDB0033527
     RDKit          3D
Dehydroisochalciporone
 37 37  0  0  0  0  0  0  0  0999 V2000
    6.4030    0.6847    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653    0.3775    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -1.0429    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -1.6954    0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.9407    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -1.6173    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -0.2776    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.0362   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1746    1.2966   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    1.5931   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404    0.6670   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    1.2461   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    0.7107   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6652    1.7659   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8426   -0.4624    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0786   -1.5307    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454   -1.7362   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390   -0.7458   -0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6147    1.6351   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9446   -0.1805   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172    0.6716    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.9320    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    0.7919   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -3.0469    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5652   -2.4089    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    0.5696    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.8646    0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    2.1264   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3169    2.6862   -0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    0.4111   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3523    2.7625   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.7314    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6646    1.4670   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7053   -0.4475    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -2.3239    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -2.7407   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008   -1.0282   -1.4153 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methyl-2-(7-oxo-1,3,5-nonatrienyl)-3H-azepine	HMDB

Chemical Formula

C₁₆H₁₉NO

Average Molecular Weight

241.3282

Monoisotopic Molecular Weight

241.146664235

IUPAC Name

(4Z,6E,8Z)-9-(2-methyl-2H-azepin-7-yl)nona-4,6,8-trien-3-one

Traditional Name

(4Z,6E,8Z)-9-(7-methyl-7H-azepin-2-yl)nona-4,6,8-trien-3-one

CAS Registry Number

Not Available

SMILES

CCC(=O)\C=C/C=C/C=C\C1=NC(C)C=CC=C1

InChI Identifier

InChI=1S/C16H19NO/c1-3-16(18)13-7-5-4-6-11-15-12-9-8-10-14(2)17-15/h4-14H,3H2,1-2H3/b5-4+,11-6-,13-7-

InChI Key

WJIGOTVFVWHJRY-BYWROCKKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketimine
Ketone
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Imine
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033527)

Cellular substructure

Membrane (HMDB: HMDB0033527)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033527)

Source

Exogenous

Food

Food (HMDB: HMDB0033527)

Plant (HMDB: HMDB0033527)

Not Available

Nutrient (HMDB: HMDB0033527)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
logP	4.09	ALOGPS
logP	3.93	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.5 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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
DeepCCS	[M+H]+	163.246	30932474
DeepCCS	[M-H]-	160.888	30932474
DeepCCS	[M-2H]-	193.775	30932474
DeepCCS	[M+Na]+	169.339	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.7	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroisochalciporone	CCC(=O)\C=C/C=C/C=C\C1=NC(C)C=CC=C1	3257.2	Standard polar	33892256
Dehydroisochalciporone	CCC(=O)\C=C/C=C/C=C\C1=NC(C)C=CC=C1	2196.9	Standard non polar	33892256
Dehydroisochalciporone	CCC(=O)\C=C/C=C/C=C\C1=NC(C)C=CC=C1	2295.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroisochalciporone,1TMS,isomer #1	CC=C(/C=C\C=C\C=C/C1=NC(C)C=CC=C1)O[Si](C)(C)C	2481.1	Semi standard non polar	33892256
Dehydroisochalciporone,1TMS,isomer #1	CC=C(/C=C\C=C\C=C/C1=NC(C)C=CC=C1)O[Si](C)(C)C	2122.1	Standard non polar	33892256
Dehydroisochalciporone,1TBDMS,isomer #1	CC=C(/C=C\C=C\C=C/C1=NC(C)C=CC=C1)O[Si](C)(C)C(C)(C)C	2657.1	Semi standard non polar	33892256
Dehydroisochalciporone,1TBDMS,isomer #1	CC=C(/C=C\C=C\C=C/C1=NC(C)C=CC=C1)O[Si](C)(C)C(C)(C)C	2354.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroisochalciporone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05e9-5930000000-08b18d31bdcc2ef1e76e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroisochalciporone 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 - Dehydroisochalciporone 10V, Positive-QTOF	splash10-0006-0190000000-bf59ae30f893c30b434a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 20V, Positive-QTOF	splash10-0596-5930000000-51e7577597c587070f40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 40V, Positive-QTOF	splash10-0pdi-9300000000-89bd69cb7926f9e8ad42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 10V, Negative-QTOF	splash10-0006-0090000000-f884a4da7ecfe1f9779f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 20V, Negative-QTOF	splash10-0006-2390000000-5e051d2ef13005afa11e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 40V, Negative-QTOF	splash10-01ox-9720000000-8b1c80434a54801c5e2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 10V, Positive-QTOF	splash10-0006-0290000000-fee9c049b94bf60e4d36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 20V, Positive-QTOF	splash10-006x-1920000000-c55d36cb37e6d57bde28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 40V, Positive-QTOF	splash10-0arr-2910000000-1e37b228846ba760e0f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 10V, Negative-QTOF	splash10-0006-0290000000-5b5bc1a8f45d54ecaab8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 20V, Negative-QTOF	splash10-0006-2970000000-806b6ff7cd98dbd1ce84	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroisochalciporone 40V, Negative-QTOF	splash10-0aor-0900000000-20e87b2ed11c0a1e2ef4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB011584

KNApSAcK ID

Not Available

Chemspider ID

35013623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751448

PDB ID

Not Available

ChEBI ID

169784

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Dehydroisochalciporone (HMDB0033527)

MOL for HMDB0033527 (Dehydroisochalciporone)

3D MOL for HMDB0033527 (Dehydroisochalciporone)

3D SDF for HMDB0033527 (Dehydroisochalciporone)

3D-SDF for HMDB0033527 (Dehydroisochalciporone)

PDB for HMDB0033527 (Dehydroisochalciporone)

3D PDB for HMDB0033527 (Dehydroisochalciporone)

SMILES for HMDB0033527 (Dehydroisochalciporone)

INCHI for HMDB0033527 (Dehydroisochalciporone)

Structure for HMDB0033527 (Dehydroisochalciporone)

3D Structure for HMDB0033527 (Dehydroisochalciporone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra