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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:58:31 UTC

Update Date

2022-03-07 02:56:13 UTC

HMDB ID

HMDB0039493

Secondary Accession Numbers

HMDB39493

Metabolite Identification

Common Name

Dihydrowyerone acid

Description

Dihydrowyerone acid belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. Based on a literature review a small amount of articles have been published on Dihydrowyerone acid.

Structure

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

HMDB0039493
     RDKit          3D
Dihydrowyerone acid
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.9921   -1.7742   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478   -0.8951    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4636    0.5192    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4595    1.4177    1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    1.5274    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.6037   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    1.7174   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    2.5126   -1.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507    0.9021   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2182    0.0026    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -0.5291    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.0529   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969   -0.0520   -1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736   -0.3417   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.6103    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8702   -0.5803    1.5821 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -0.9672    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751    0.9072   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.8387   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9477   -1.6828   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0201   -1.5201   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.8775   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802   -1.3260    1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.9687   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3460    0.4461    1.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    2.4272    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    1.0792    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -0.2623    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -1.3188    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779    0.1396   -2.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -0.3932   -1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -0.2544    1.1316 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  3  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 18  1  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
M  END


  Mrv0541 05061311112D          

 18 18  0  0  0  0            999 V2000
    3.4256    5.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    4.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -2.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  3  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039493

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-2-3-4-5-6-12(15)13-9-7-11(18-13)8-10-14(16)17/h7-10H,2-4H2,1H3,(H,16,17)/b10-8-

> <INCHI_KEY>
RZGRQFVNPYQSLD-NTMALXAHSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.2586

> <EXACT_MASS>
246.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.16446771739696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[5-(hept-2-ynoyl)furan-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.249433082

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.209217204077244

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3556469375049245

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
68.1752

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[5-(hept-2-ynoyl)furan-2-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039493
     RDKit          3D
Dihydrowyerone acid
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.9921   -1.7742   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478   -0.8951    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4636    0.5192    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4595    1.4177    1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    1.5274    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.6037   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    1.7174   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    2.5126   -1.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507    0.9021   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2182    0.0026    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -0.5291    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.0529   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969   -0.0520   -1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736   -0.3417   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.6103    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8702   -0.5803    1.5821 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -0.9672    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751    0.9072   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.8387   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9477   -1.6828   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0201   -1.5201   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.8775   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802   -1.3260    1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.9687   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3460    0.4461    1.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    2.4272    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    1.0792    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -0.2623    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -1.3188    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779    0.1396   -2.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -0.3932   -1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -0.2544    1.1316 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  3  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 18  1  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 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       6.394   9.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.394   8.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.061   7.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.727   5.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.543  -3.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.169  -4.510   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.448  -1.858   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   12                                                       
CONECT    7    9   11                                                       
CONECT    8   10   11                                                       
CONECT    9    7   13                                                       
CONECT   10    8   14                                                       
CONECT   11    7    8   18                                                  
CONECT   12    6   13   15                                                  
CONECT   13    9   12   18                                                  
CONECT   14   10   16   17                                                  
CONECT   15   12                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0039493
HETATM    1  C1  UNL     1      -4.992  -1.774  -0.292  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.948  -0.895   0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.464   0.519   0.538  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.460   1.418   1.177  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.234   1.527   0.400  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.231   1.604  -0.244  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.038   1.717  -1.015  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.002   2.513  -1.975  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.151   0.902  -0.682  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.218   0.003   0.348  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.513  -0.529   0.286  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.170   0.053  -0.748  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.497  -0.052  -1.302  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.574  -0.342  -0.680  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.722  -0.610   0.703  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.870  -0.580   1.582  1.00  0.00           O  
HETATM   17  O3  UNL     1       7.037  -0.967   1.155  1.00  0.00           O  
HETATM   18  O4  UNL     1       2.275   0.907  -1.286  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.837  -2.839  -0.039  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.948  -1.683  -1.407  1.00  0.00           H  
HETATM   21  H3  UNL     1      -6.020  -1.520  -0.000  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.077  -0.877  -0.348  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.580  -1.326   1.298  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.801   0.969  -0.396  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.346   0.446   1.207  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.912   2.427   1.259  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.260   1.079   2.217  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.442  -0.262   1.076  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.817  -1.319   0.967  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.578   0.140  -2.425  1.00  0.00           H  
HETATM   31  H13 UNL     1       6.529  -0.393  -1.287  1.00  0.00           H  
HETATM   32  H14 UNL     1       7.756  -0.254   1.132  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6    6    6
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   18
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   18
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   17
CONECT   17   32
END

HMDB0039493
     RDKit          3D
Dihydrowyerone acid
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.9921   -1.7742   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478   -0.8951    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4636    0.5192    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4595    1.4177    1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    1.5274    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.6037   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    1.7174   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    2.5126   -1.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507    0.9021   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2182    0.0026    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -0.5291    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.0529   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969   -0.0520   -1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736   -0.3417   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.6103    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8702   -0.5803    1.5821 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -0.9672    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751    0.9072   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.8387   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9477   -1.6828   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0201   -1.5201   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.8775   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802   -1.3260    1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.9687   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3460    0.4461    1.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    2.4272    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    1.0792    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -0.2623    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -1.3188    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779    0.1396   -2.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -0.3932   -1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -0.2544    1.1316 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  3  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 18  1  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2Z)-3-[5-(Hept-2-ynoyl)furan-2-yl]prop-2-enoate	HMDB

Chemical Formula

C₁₄H₁₄O₄

Average Molecular Weight

246.2586

Monoisotopic Molecular Weight

246.089208936

IUPAC Name

(2Z)-3-[5-(hept-2-ynoyl)furan-2-yl]prop-2-enoic acid

Traditional Name

(2Z)-3-[5-(hept-2-ynoyl)furan-2-yl]prop-2-enoic acid

CAS Registry Number

70711-57-8

SMILES

CCCCC#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

InChI Identifier

InChI=1S/C14H14O4/c1-2-3-4-5-6-12(15)13-9-7-11(18-13)8-10-14(16)17/h7-10H,2-4H2,1H3,(H,16,17)/b10-8-

InChI Key

RZGRQFVNPYQSLD-NTMALXAHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Aryl ketone
Furan
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0039493)

Cellular substructure

Extracellular (HMDB: HMDB0039493)
Membrane (HMDB: HMDB0039493)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039493)

Source

Endogenous

Endogenous (HMDB: HMDB0039493)

Plant

Fabaceae (HMDB: HMDB0039493)

Animal

Animal (HMDB: HMDB0039493)

Exogenous

Food

Food (HMDB: HMDB0039493)

Pulse

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039493)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039493)

Cellular process

Cell signaling (HMDB: HMDB0039493)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039493)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039493)

Nutrient

Nutrient (HMDB: HMDB0039493)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039493)

Emulsifier (HMDB: HMDB0039493)

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	0.03 g/L	ALOGPS
logP	3.13	ALOGPS
logP	3.25	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.21	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.18 m³·mol⁻¹	ChemAxon
Polarizability	26.16 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
DeepCCS	[M+H]+	157.597	30932474
DeepCCS	[M-H]-	155.239	30932474
DeepCCS	[M-2H]-	188.125	30932474
DeepCCS	[M+Na]+	163.691	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	161.9	32859911
AllCCS	[M+Na]+	162.9	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	159.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrowyerone acid	CCCCC#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	3688.0	Standard polar	33892256
Dihydrowyerone acid	CCCCC#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	2070.4	Standard non polar	33892256
Dihydrowyerone acid	CCCCC#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	2183.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrowyerone acid,1TMS,isomer #1	CCCCC#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C)O1	2310.7	Semi standard non polar	33892256
Dihydrowyerone acid,1TBDMS,isomer #1	CCCCC#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O1	2538.8	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 - Dihydrowyerone acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3930000000-9a01f14bc65ad8697664	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrowyerone acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fj0-9541000000-16b56f449c91d0210b3c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrowyerone acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrowyerone acid 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 - Dihydrowyerone acid 10V, Negative-QTOF	splash10-0002-1290000000-be7024ade7a0fc65c21d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 20V, Negative-QTOF	splash10-0f7k-6970000000-afb6799fd6eb9893c475	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 40V, Negative-QTOF	splash10-0aou-9500000000-5f76e82cdc61a287aa11	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 10V, Negative-QTOF	splash10-0002-0190000000-cccaf0e4c2ba5e521e4d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 20V, Negative-QTOF	splash10-0007-9330000000-265c605f0b432b04831b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 40V, Negative-QTOF	splash10-00kf-9100000000-5872f48f8afafec5b072	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 10V, Positive-QTOF	splash10-002b-0190000000-d9f739d94a7fd1002d3e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 20V, Positive-QTOF	splash10-0019-8940000000-cdc48e91f68ee19006a8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 40V, Positive-QTOF	splash10-00kf-9200000000-2ce116d5d0a8b67ea106	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 10V, Positive-QTOF	splash10-0002-0290000000-3785ff98dbaefdf77841	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 20V, Positive-QTOF	splash10-000i-4930000000-6f57d8914e72a54a32a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowyerone acid 40V, Positive-QTOF	splash10-000e-9400000000-561aa32d2a0741e0367d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019100

KNApSAcK ID

C00054429

Chemspider ID

30777349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752660

PDB ID

Not Available

ChEBI ID

174274

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

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dihydrowyerone acid (HMDB0039493)

MOL for HMDB0039493 (Dihydrowyerone acid)

3D MOL for HMDB0039493 (Dihydrowyerone acid)

3D SDF for HMDB0039493 (Dihydrowyerone acid)

3D-SDF for HMDB0039493 (Dihydrowyerone acid)

PDB for HMDB0039493 (Dihydrowyerone acid)

3D PDB for HMDB0039493 (Dihydrowyerone acid)

SMILES for HMDB0039493 (Dihydrowyerone acid)

INCHI for HMDB0039493 (Dihydrowyerone acid)

Structure for HMDB0039493 (Dihydrowyerone acid)

3D Structure for HMDB0039493 (Dihydrowyerone acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra