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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:59 UTC

Update Date

2022-03-07 02:52:45 UTC

HMDB ID

HMDB0030946

Secondary Accession Numbers

HMDB30946

Metabolite Identification

Common Name

(2E,11Z)-Wyerone acid

Description

(2E,11Z)-Wyerone 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 (2E,11Z)-Wyerone acid.

Structure

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

HMDB0030946
     RDKit          3D
(2E,11Z)-Wyerone acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -5.6314   -0.4761   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3915    0.3930   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2908    1.3474    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2381    1.2821    1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247    0.2909    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823   -0.5533    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953   -1.5733    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098   -2.7790    0.2055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -1.1481    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -2.0114    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2438    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.0310    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.2766    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.6384   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029    0.8560   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4944    1.4114   -1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1803   -0.3719   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956    0.0349    0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3994   -1.3255   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5231    0.0656   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8283   -0.8556   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    0.9746   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267   -0.2773   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.0959    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    1.9945    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006   -3.0607   -0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930   -1.7134   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263    2.0783    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    2.6746    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284   -1.0557   -1.6436 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
  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
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END


  Mrv0541 05061305372D          

 18 18  0  0  0  0            999 V2000
    4.1401    1.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.7643    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
    1.3113   -0.9952    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
   -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  2  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>
HMDB0030946

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c1-2-3-4-5-6-12(15)13-9-7-11(18-13)8-10-14(16)17/h3-4,7-10H,2H2,1H3,(H,16,17)/b4-3-,10-8-

> <INCHI_KEY>
ZLZFXXJOALTVDA-YHOGECKDSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.2427

> <EXACT_MASS>
244.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.128530228542303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.887511425333333

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1982938041684146

> <JCHEM_PKA_STRONGEST_BASIC>
-4.361007531616113

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
69.2918

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030946
     RDKit          3D
(2E,11Z)-Wyerone acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -5.6314   -0.4761   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3915    0.3930   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2908    1.3474    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2381    1.2821    1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247    0.2909    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823   -0.5533    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953   -1.5733    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098   -2.7790    0.2055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -1.1481    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -2.0114    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2438    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.0310    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.2766    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.6384   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029    0.8560   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4944    1.4114   -1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1803   -0.3719   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956    0.0349    0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3994   -1.3255   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5231    0.0656   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8283   -0.8556   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    0.9746   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267   -0.2773   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.0959    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    1.9945    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006   -3.0607   -0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930   -1.7134   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263    2.0783    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    2.6746    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284   -1.0557   -1.6436 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
  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
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  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       7.728   2.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.394   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.394   5.160   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       2.448  -1.858   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.169  -4.510   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    HMDB0030946
HETATM    1  C1  UNL     1      -5.631  -0.476  -0.750  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.392   0.393  -0.831  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.291   1.347   0.288  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.238   1.282   1.088  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.225   0.291   0.849  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.382  -0.553   0.634  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.395  -1.573   0.369  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.710  -2.779   0.206  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.010  -1.148   0.295  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.051  -2.011   0.050  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.233  -1.244   0.056  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.842   0.031   0.299  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.541   1.277   0.411  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.644   1.638  -0.178  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.403   0.856  -1.102  1.00  0.00           C  
HETATM   16  O2  UNL     1       6.494   1.411  -1.518  1.00  0.00           O  
HETATM   17  O3  UNL     1       5.180  -0.372  -1.634  1.00  0.00           O  
HETATM   18  O4  UNL     1       1.496   0.035   0.437  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.399  -1.326  -0.066  1.00  0.00           H  
HETATM   20  H2  UNL     1      -6.523   0.066  -0.430  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.828  -0.856  -1.789  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.395   0.975  -1.795  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.527  -0.277  -0.862  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.063   2.096   0.462  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.190   1.995   1.900  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.001  -3.061  -0.115  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.193  -1.713  -0.064  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.126   2.078   1.094  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.048   2.675   0.059  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.928  -1.056  -1.644  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6    6
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   18
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   18
CONECT   13   14   14   28
CONECT   14   15   29
CONECT   15   16   16   17
CONECT   17   30
END

HMDB0030946
     RDKit          3D
(2E,11Z)-Wyerone acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -5.6314   -0.4761   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3915    0.3930   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2908    1.3474    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2381    1.2821    1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247    0.2909    0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823   -0.5533    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953   -1.5733    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098   -2.7790    0.2055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -1.1481    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -2.0114    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2438    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421    0.0310    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.2766    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.6384   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029    0.8560   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4944    1.4114   -1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1803   -0.3719   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956    0.0349    0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3994   -1.3255   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5231    0.0656   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8283   -0.8556   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    0.9746   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267   -0.2773   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.0959    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    1.9945    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006   -3.0607   -0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930   -1.7134   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263    2.0783    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    2.6746    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284   -1.0557   -1.6436 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
  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
  4 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoate	HMDB

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.2427

Monoisotopic Molecular Weight

244.073558872

IUPAC Name

(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

Traditional Name

(2Z)-3-{5-[(4Z)-hept-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H12O4/c1-2-3-4-5-6-12(15)13-9-7-11(18-13)8-10-14(16)17/h3-4,7-10H,2H2,1H3,(H,16,17)/b4-3-,10-8-

InChI Key

ZLZFXXJOALTVDA-YHOGECKDSA-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0030946)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0030946)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030946)

Source

Endogenous

Endogenous (HMDB: HMDB0030946)

Plant

Fabaceae (HMDB: HMDB0030946)

Animal

Animal (HMDB: HMDB0030946)

Exogenous

Food

Food (HMDB: HMDB0030946)

Pulse

Bean

Broad bean (FooDB: FOOD00197)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030946)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030946)

Lipid metabolism pathway (HMDB: HMDB0030946)

Cellular process

Cell signaling (HMDB: HMDB0030946)

Biochemical process

Lipid transport (HMDB: HMDB0030946)

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0030946)

Pesticide (HMDB: HMDB0030946)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030946)

Biological role

Energy source (HMDB: HMDB0030946)
Phytoalexin (HMDB: HMDB0030946)

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	0.026 g/L	ALOGPS
logP	2.94	ALOGPS
logP	2.89	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.2	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	6	ChemAxon
Refractivity	69.29 m³·mol⁻¹	ChemAxon
Polarizability	25.13 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]+	155.893	30932474
DeepCCS	[M-H]-	153.535	30932474
DeepCCS	[M-2H]-	186.421	30932474
DeepCCS	[M+Na]+	161.986	30932474
AllCCS	[M+H]+	157.0	32859911
AllCCS	[M+H-H2O]+	153.1	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.7	32859911
AllCCS	[M-H]-	155.8	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.99 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0222 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2147.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	430.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	275.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	574.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	655.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1353.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	476.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1413.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	433.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E,11Z)-Wyerone acid	CC\C=C/C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	3784.1	Standard polar	33892256
(2E,11Z)-Wyerone acid	CC\C=C/C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	2090.7	Standard non polar	33892256
(2E,11Z)-Wyerone acid	CC\C=C/C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	2247.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2E,11Z)-Wyerone acid,1TMS,isomer #1	CC/C=C\C#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C)O1	2314.1	Semi standard non polar	33892256
(2E,11Z)-Wyerone acid,1TBDMS,isomer #1	CC/C=C\C#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O1	2550.1	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 - (2E,11Z)-Wyerone acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1930000000-80ffc6c9056df3985ac7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,11Z)-Wyerone acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fni-9853000000-6f5bbf69288fd7a46605	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,11Z)-Wyerone 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 - (2E,11Z)-Wyerone acid 10V, Positive-QTOF	splash10-002b-0290000000-1b5cae0b6292bd71f28d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 20V, Positive-QTOF	splash10-005j-6920000000-039155bd484317125ea2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 40V, Positive-QTOF	splash10-0fvl-9300000000-6b5685d2b4e1fb59134b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 10V, Negative-QTOF	splash10-0006-1490000000-50d0b0d622b9fb04a810	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 20V, Negative-QTOF	splash10-002g-4940000000-d466f031b16c755b2d33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 40V, Negative-QTOF	splash10-0aou-9700000000-6c45af926edc6d70f843	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 10V, Positive-QTOF	splash10-0002-1290000000-eb733c9467de404fa16b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 20V, Positive-QTOF	splash10-0kg9-4940000000-598b00dc886e8b1d7180	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 40V, Positive-QTOF	splash10-002b-9300000000-3eef0f66a177eb69bebb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 10V, Negative-QTOF	splash10-0006-0390000000-bff68b9440cdda8d7f97	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 20V, Negative-QTOF	splash10-0007-9610000000-2dc0276f14dd2b32f8f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,11Z)-Wyerone acid 40V, Negative-QTOF	splash10-0006-9100000000-166a7ab7f3d1342b6499	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

FDB002923

KNApSAcK ID

Not Available

Chemspider ID

30776870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751103

PDB ID

Not Available

ChEBI ID

174257

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 (2E,11Z)-Wyerone acid (HMDB0030946)

MOL for HMDB0030946 ((2E,11Z)-Wyerone acid)

3D MOL for HMDB0030946 ((2E,11Z)-Wyerone acid)

3D SDF for HMDB0030946 ((2E,11Z)-Wyerone acid)

3D-SDF for HMDB0030946 ((2E,11Z)-Wyerone acid)

PDB for HMDB0030946 ((2E,11Z)-Wyerone acid)

3D PDB for HMDB0030946 ((2E,11Z)-Wyerone acid)

SMILES for HMDB0030946 ((2E,11Z)-Wyerone acid)

INCHI for HMDB0030946 ((2E,11Z)-Wyerone acid)

Structure for HMDB0030946 ((2E,11Z)-Wyerone acid)

3D Structure for HMDB0030946 ((2E,11Z)-Wyerone acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra