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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000560

Secondary Accession Numbers

HMDB0039129
HMDB00560
HMDB39129

Metabolite Identification

Common Name

Goshuyic acid

Description

Goshuyic acid, also known as (Z,Z)-5,8-tetradecadienoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Goshuyic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, goshuyic acid is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Goshuyic acid is an intermediate of unsaturated fatty acid oxidation. An increase of goshuyic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders (PMID: 7586519 ). Goshuyic acid is found in fats and oils and is a minor constituent of rape oil.

Structure

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

HMDB0000560
     RDKit          3D
Goshuyic acid
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.6312   -0.2987   -0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    0.6460   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3662    0.1972    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.0982    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    0.6895    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.6797    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4161   -1.0352    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890   -0.0777    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -0.3272    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213   -0.6262    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -0.7365   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    0.2440   -1.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6867    0.1195   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.3608    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988    1.3750    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5649   -0.4827    1.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3928   -0.1210   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -0.0595    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523   -1.3445   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7992    1.6891   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0736    0.6010   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278    0.3258    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441   -0.8604    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    2.1290    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602    1.0659   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311    0.7046    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.4900    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -1.4648    0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1180    0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.9971    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.1213   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.2583    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.8323    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -0.6512   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.7654   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9970    1.3098   -1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253    0.2415   -2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1578   -0.8765   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3713    0.8781   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1748   -1.4253    1.5826 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
M  END

      
  Mrv1652305261800062D          

 16 15  0  0  0  0            999 V2000
10012.586610013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.302310012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.018110013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.843710013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.558510012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.273310013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.988110012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.703110013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.417910012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.761710013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.046110012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.330610013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.616910012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.901410013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.187710012.7142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.901410013.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000560

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6-,10-9-

> <INCHI_KEY>
HXHZGHRLVRFQDR-HZJYTTRNSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.525730404385264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z)-tetradeca-5,8-dienoic acid

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.643602134333333

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z)-tetradeca-5,8-dienoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000560
     RDKit          3D
Goshuyic acid
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.6312   -0.2987   -0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    0.6460   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3662    0.1972    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.0982    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    0.6895    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.6797    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4161   -1.0352    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890   -0.0777    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -0.3272    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213   -0.6262    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -0.7365   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    0.2440   -1.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6867    0.1195   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.3608    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988    1.3750    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5649   -0.4827    1.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3928   -0.1210   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -0.0595    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523   -1.3445   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7992    1.6891   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0736    0.6010   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278    0.3258    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441   -0.8604    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    2.1290    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602    1.0659   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311    0.7046    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.4900    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -1.4648    0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1180    0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.9971    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.1213   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.2583    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.8323    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -0.6512   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.7654   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9970    1.3098   -1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253    0.2415   -2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1578   -0.8765   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3713    0.8781   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1748   -1.4253    1.5826 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 26-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-18         0                                  
HETATM    1  C   UNK     0    8690.1628691.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8691.4988690.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8692.8348691.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8694.3758691.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8695.7098690.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8697.0438691.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8698.3788690.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8699.7128691.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8701.0478690.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.6228691.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8687.2868690.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8685.9508691.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8684.6188690.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8683.2838691.168   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8681.9508690.400   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8683.2838692.709   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000560
HETATM    1  C1  UNL     1      -6.631  -0.299  -0.443  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.452   0.646  -0.668  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.366   0.197   0.288  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.164   1.098   0.093  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.026   0.690   1.026  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.604  -0.680   0.815  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.416  -1.035   0.440  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.689  -0.078   0.174  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.853  -0.327   1.030  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.021  -0.626   0.487  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.292  -0.736  -0.926  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.337   0.244  -1.385  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.687   0.120  -0.793  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.842   0.361   0.633  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.299   1.375   1.172  1.00  0.00           O  
HETATM   16  O2  UNL     1       6.565  -0.483   1.438  1.00  0.00           O  
HETATM   17  H1  UNL     1      -7.393  -0.121  -1.207  1.00  0.00           H  
HETATM   18  H2  UNL     1      -7.051  -0.059   0.546  1.00  0.00           H  
HETATM   19  H3  UNL     1      -6.252  -1.344  -0.515  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.799   1.689  -0.439  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.074   0.601  -1.707  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.728   0.326   1.326  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.144  -0.860   0.034  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.490   2.129   0.343  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.760   1.066  -0.922  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.531   0.705   2.052  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.311   1.490   1.048  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.364  -1.465   0.992  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.211  -2.118   0.312  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.380   0.997   0.347  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.851  -0.121  -0.907  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.731  -0.258   2.122  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.845  -0.832   1.204  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.463  -0.651  -1.635  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.788  -1.765  -1.158  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.997   1.310  -1.182  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.425   0.242  -2.514  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.158  -0.876  -1.020  1.00  0.00           H  
HETATM   39  H23 UNL     1       6.371   0.878  -1.304  1.00  0.00           H  
HETATM   40  H24 UNL     1       6.175  -1.425   1.583  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   15   16
CONECT   16   40
END

HMDB0000560
     RDKit          3D
Goshuyic acid
 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.6312   -0.2987   -0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    0.6460   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3662    0.1972    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.0982    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    0.6895    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -0.6797    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4161   -1.0352    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890   -0.0777    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -0.3272    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213   -0.6262    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -0.7365   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    0.2440   -1.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6867    0.1195   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.3608    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988    1.3750    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5649   -0.4827    1.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3928   -0.1210   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -0.0595    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523   -1.3445   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7992    1.6891   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0736    0.6010   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278    0.3258    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1441   -0.8604    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    2.1290    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602    1.0659   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311    0.7046    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.4900    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -1.4648    0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1180    0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.9971    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.1213   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -0.2583    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.8323    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -0.6512   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.7654   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9970    1.3098   -1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253    0.2415   -2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1578   -0.8765   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3713    0.8781   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1748   -1.4253    1.5826 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z,Z)-5,8-Tetradecadienoic acid	ChEBI
(Z,Z)-Tetradeca-5,8-dienoic acid	ChEBI
(cis,cis-delta(5),delta(8))-Tetradecanoate	Generator
(cis,cis-Δ(5),δ(8))-tetradecanoate	Generator
(cis,cis-Δ(5),δ(8))-tetradecanoic acid	Generator
(cis-delta(5),cis-delta(8))-Tetradecanoate	Generator
(cis-Δ(5),cis-δ(8))-tetradecanoate	Generator
(cis-Δ(5),cis-δ(8))-tetradecanoic acid	Generator
(Z,Z)-5,8-Tetradecadienoate	Generator
(Z,Z)-Tetradeca-5,8-dienoate	Generator
Goshuyate	Generator
5,8-Tetradecadienoate	HMDB
(cis,cis-Δ5,δ8)-tetradecanoic acid	HMDB
(cis-Δ5,cis-δ8)-tetradecanoic acid	HMDB
(cis,cis-delta5,delta8)-Tetradecanoic acid	HMDB
(cis-delta5,cis-delta8)-Tetradecanoic acid	HMDB
(5Z,8Z)-5,8-Tetradecadienoic acid	HMDB
cis,cis-Tetradeca-5,8-dienoic acid	HMDB
5,8-Tetradecadienoic acid	HMDB
FA(14:2(5Z,8Z))	HMDB

Chemical Formula

C₁₄H₂₄O₂

Average Molecular Weight

224.3392

Monoisotopic Molecular Weight

224.177630012

IUPAC Name

(5Z,8Z)-tetradeca-5,8-dienoic acid

Traditional Name

(5Z,8Z)-tetradeca-5,8-dienoic acid

CAS Registry Number

39039-37-7

SMILES

CCCCC\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6-,10-9-

InChI Key

HXHZGHRLVRFQDR-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:70719 )
polyunsaturated fatty acid (CHEBI:70719 )
Unsaturated fatty acids (LMFA01030257 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000560)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000560)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000560)

Source

Endogenous

Endogenous (HMDB: HMDB0000560)

Animal

Animal (HMDB: HMDB0000560)

Exogenous

Food

Food (HMDB: HMDB0000560)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0000560)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000560)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000560)

Lipid metabolism pathway (HMDB: HMDB0000560)

Cellular process

Cell signaling (HMDB: HMDB0000560)

Biochemical process

Lipid transport (HMDB: HMDB0000560)

Role

Biological role

Energy source (HMDB: HMDB0000560)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000560)

Physical Properties

State

Solid

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	0.0042 g/L	ALOGPS
logP	5.35	ALOGPS
logP	4.64	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	70.11 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.708	31661259
DarkChem	[M-H]-	161.323	31661259
AllCCS	[M+H]+	158.881	32859911
AllCCS	[M-H]-	161.386	32859911
DeepCCS	[M+H]+	162.586	30932474
DeepCCS	[M-H]-	158.566	30932474
DeepCCS	[M-2H]-	195.737	30932474
DeepCCS	[M+Na]+	171.561	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.2	32859911
AllCCS	[M+Na]+	163.1	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Goshuyic acid	CCCCC\C=C/C\C=C/CCCC(O)=O	2819.3	Standard polar	33892256
Goshuyic acid	CCCCC\C=C/C\C=C/CCCC(O)=O	1686.7	Standard non polar	33892256
Goshuyic acid	CCCCC\C=C/C\C=C/CCCC(O)=O	1753.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Goshuyic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	1815.5	Semi standard non polar	33892256
Goshuyic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2051.3	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 - Goshuyic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-70f7fb8887a89cfdd4ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Goshuyic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9520000000-89f5676bfb6d4fb2807c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Goshuyic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Goshuyic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Goshuyic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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 - Goshuyic acid 10V, Positive-QTOF	splash10-056r-0390000000-9c40c473d414e0052f16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 20V, Positive-QTOF	splash10-056r-6930000000-baeaeb0eeb65ca411f5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 40V, Positive-QTOF	splash10-052f-9400000000-2ccf4ba98ffea6f7575b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 10V, Negative-QTOF	splash10-00di-0190000000-4be544b58785fc9fe7b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 20V, Negative-QTOF	splash10-00fr-1590000000-0cc9e5963e8a02c9a79b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 40V, Negative-QTOF	splash10-0a4i-9400000000-156577ed3ac682dbd097	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 10V, Positive-QTOF	splash10-0560-9420000000-5da9b03ee314f3e163e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 20V, Positive-QTOF	splash10-067m-9100000000-76e8cc4c6c9bd8d279b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 40V, Positive-QTOF	splash10-067l-9000000000-f0a2bab062fd7b1916dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 10V, Negative-QTOF	splash10-00di-0090000000-a15027b0e036a485ad3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 20V, Negative-QTOF	splash10-05fr-1190000000-618d69367ae6d95cfebd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Goshuyic acid 40V, Negative-QTOF	splash10-052f-9300000000-b32b2c37ff62cf641b60	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB018642

KNApSAcK ID

Not Available

Chemspider ID

4471834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5544

PubChem Compound

5312409

PDB ID

Not Available

ChEBI ID

70719

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Guex, Waldemar; Rueegg, Rudolf; Schwieter, Ulrich. Unsaturated alcohols and their esters. (1960), DE 1111615 19600129 CAN 56:31075 AN 1962:31075

Material Safety Data Sheet (MSDS)

Not Available

General References

Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
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 Goshuyic acid (HMDB0000560)

MOL for HMDB0000560 (Goshuyic acid)

3D MOL for HMDB0000560 (Goshuyic acid)

3D SDF for HMDB0000560 (Goshuyic acid)

3D-SDF for HMDB0000560 (Goshuyic acid)

PDB for HMDB0000560 (Goshuyic acid)

3D PDB for HMDB0000560 (Goshuyic acid)

SMILES for HMDB0000560 (Goshuyic acid)

INCHI for HMDB0000560 (Goshuyic acid)

Structure for HMDB0000560 (Goshuyic acid)

3D Structure for HMDB0000560 (Goshuyic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra