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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:25:25 UTC

Update Date

2022-03-07 02:56:45 UTC

HMDB ID

HMDB0040833

Secondary Accession Numbers

HMDB40833

Metabolite Identification

Common Name

3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal

Description

3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal has been detected, but not quantified in, citrus. This could make 3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal.

Structure

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

HMDB0040833
     RDKit          3D
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1742    1.4405    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520    0.2271   -0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882    0.2103   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273   -0.8175   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.7992    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181   -0.9416    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.1641    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1232    0.0957   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569    1.3075   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    1.2990   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464    2.5829   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    2.5744   -0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.1407   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588   -2.2728   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -2.1782    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.2692    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    2.1993    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830    1.9306    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    1.2278    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0777   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316   -0.5656   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416    1.2303   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544   -1.6616   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754    0.1723    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -1.5547    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    1.1619    0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265    2.2736    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971    0.3895   -0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.4989   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.2646   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -3.2410   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090   -4.2016   -0.1323 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  6  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
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
M  END


  Mrv0541 05061312092D          

 16 16  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  2  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  2  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040833

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O2/c1-11(2)5-7-13-10-12(4-3-9-15)6-8-14(13)16/h3-6,8-10,16H,7H2,1-2H3/b4-3+

> <INCHI_KEY>
FNDJBOATFIWAJR-ONEGZZNKSA-N

> <FORMULA>
C14H16O2

> <MOLECULAR_WEIGHT>
216.2756

> <EXACT_MASS>
216.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.848800406390694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.4024716853333334

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.849162083924986

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3466227847943095

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.3582

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040833
     RDKit          3D
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1742    1.4405    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520    0.2271   -0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882    0.2103   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273   -0.8175   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.7992    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181   -0.9416    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.1641    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1232    0.0957   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569    1.3075   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    1.2990   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464    2.5829   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    2.5744   -0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.1407   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588   -2.2728   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -2.1782    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.2692    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    2.1993    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830    1.9306    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    1.2278    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0777   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316   -0.5656   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416    1.2303   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544   -1.6616   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754    0.1723    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -1.5547    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    1.1619    0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265    2.2736    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971    0.3895   -0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.4989   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.2646   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -3.2410   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090   -4.2016   -0.1323 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  6  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
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9    3   15                                                       
CONECT   10   12   13                                                       
CONECT   11    1    2    5                                                  
CONECT   12    4    6   10                                                  
CONECT   13    7   10   14                                                  
CONECT   14    8   13   16                                                  
CONECT   15    9                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0040833
HETATM    1  C1  UNL     1      -3.174   1.440   0.512  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.252   0.227  -0.335  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.288   0.210  -1.408  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.427  -0.817  -0.148  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.414  -0.799   0.904  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.018  -0.942   0.442  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.803   0.164   0.390  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.123   0.096  -0.033  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.957   1.307  -0.068  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.214   1.299  -0.457  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.946   2.583  -0.447  1.00  0.00           C  
HETATM   12  O1  UNL     1       6.143   2.574  -0.816  1.00  0.00           O  
HETATM   13  C12 UNL     1       2.585  -1.141  -0.406  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.759  -2.273  -0.358  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.463  -2.178   0.063  1.00  0.00           C  
HETATM   16  O2  UNL     1      -0.408  -3.269   0.133  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.908   2.199   0.186  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.183   1.931   0.474  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.392   1.228   1.577  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.281  -0.078  -0.950  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.032  -0.566  -2.185  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.342   1.230  -1.831  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.554  -1.662  -0.813  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.475   0.172   1.436  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.622  -1.555   1.720  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.443   1.162   0.687  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.527   2.274   0.241  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.697   0.390  -0.773  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.478   3.499  -0.137  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.599  -1.265  -0.745  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.143  -3.241  -0.656  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.109  -4.202  -0.132  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    7   15
CONECT    7    8   26
CONECT    8    9   13   13
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16
CONECT   16   32
END

HMDB0040833
     RDKit          3D
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1742    1.4405    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520    0.2271   -0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882    0.2103   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273   -0.8175   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -0.7992    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181   -0.9416    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.1641    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1232    0.0957   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569    1.3075   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    1.2990   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464    2.5829   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    2.5744   -0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.1407   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588   -2.2728   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -2.1782    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.2692    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    2.1993    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830    1.9306    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    1.2278    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0777   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316   -0.5656   -2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416    1.2303   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544   -1.6616   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754    0.1723    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -1.5547    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    1.1619    0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265    2.2736    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971    0.3895   -0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.4989   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.2646   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -3.2410   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090   -4.2016   -0.1323 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  6  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
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3-prenylcinnamaldehyde	HMDB
3-(4-Hydroxy-3-(3-methyl-2-butenyl)phenyl)-2-propenal	MeSH, HMDB
3-HMBP-2-Propenal	MeSH

Chemical Formula

C₁₄H₁₆O₂

Average Molecular Weight

216.2756

Monoisotopic Molecular Weight

216.115029756

IUPAC Name

(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

Traditional Name

(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1

InChI Identifier

InChI=1S/C14H16O2/c1-11(2)5-7-13-10-12(4-3-9-15)6-8-14(13)16/h3-6,8-10,16H,7H2,1-2H3/b4-3+

InChI Key

FNDJBOATFIWAJR-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040833)

Membrane (HMDB: HMDB0040833)
Cell membrane (HMDB: HMDB0040833)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040833)

Source

Exogenous

Food

Food (HMDB: HMDB0040833)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0040833)

Not Available

Nutrient (HMDB: HMDB0040833)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144.5 - 146 °C	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	0.017 g/L	ALOGPS
logP	3.55	ALOGPS
logP	3.4	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.36 m³·mol⁻¹	ChemAxon
Polarizability	24.85 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]+	154.475	30932474
DeepCCS	[M-H]-	152.118	30932474
DeepCCS	[M-2H]-	185.066	30932474
DeepCCS	[M+Na]+	160.569	30932474
AllCCS	[M+H]+	148.8	32859911
AllCCS	[M+H-H2O]+	144.8	32859911
AllCCS	[M+NH4]+	152.5	32859911
AllCCS	[M+Na]+	153.6	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	151.3	32859911
AllCCS	[M+HCOO]-	151.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal	CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1	3054.4	Standard polar	33892256
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal	CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1	1911.1	Standard non polar	33892256
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal	CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1	2061.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal,1TMS,isomer #1	CC(C)=CCC1=CC(/C=C/C=O)=CC=C1O[Si](C)(C)C	2115.0	Semi standard non polar	33892256
3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal,1TBDMS,isomer #1	CC(C)=CCC1=CC(/C=C/C=O)=CC=C1O[Si](C)(C)C(C)(C)C	2379.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-4920000000-7d71c35970bcc780a72c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4090000000-3c7dc38899da7069ea15	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 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 - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 10V, Positive-QTOF	splash10-014i-1980000000-560770268a0ad8f36dff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 20V, Positive-QTOF	splash10-0aor-6910000000-d3a293bf66f5067cb1f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 40V, Positive-QTOF	splash10-0aor-9500000000-a124ed5a73ba46877623	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 10V, Negative-QTOF	splash10-014i-0190000000-fe8b28f4d770777d91b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 20V, Negative-QTOF	splash10-014r-0970000000-50d2ae3f9e1f4fc975ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 40V, Negative-QTOF	splash10-006x-4900000000-54b0fe2feb0a257698d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 10V, Negative-QTOF	splash10-014i-0290000000-d32f9e91fec94b259a8b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 20V, Negative-QTOF	splash10-01bi-0930000000-9503db06392e070e4439	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 40V, Negative-QTOF	splash10-01b9-1900000000-357101b53712b6c654e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 10V, Positive-QTOF	splash10-02t9-0920000000-eae664f7eb2ef8e0cfcb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 20V, Positive-QTOF	splash10-00lr-1910000000-1d451087fe4f1e980c5c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal 40V, Positive-QTOF	splash10-067l-2900000000-1701f8ba14acbaec60ef	2021-09-25	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

FDB020655

KNApSAcK ID

Not Available

Chemspider ID

4947663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443694

PDB ID

Not Available

ChEBI ID

172456

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 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal (HMDB0040833)

MOL for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

3D MOL for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

3D SDF for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

3D-SDF for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

PDB for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

3D PDB for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

SMILES for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

INCHI for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

Structure for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

3D Structure for HMDB0040833 (3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra