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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:49:35 UTC

Update Date

2021-09-26 23:04:32 UTC

HMDB ID

HMDB0252124

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,8,11,14-Eicosatetraynoic acid

Description

5,8,11,14-eicosatetraynoic acid 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. 5,8,11,14-eicosatetraynoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,8,11,14-eicosatetraynoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5,8,11,14-Eicosatetraynoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252124
     RDKit          3D
5,8,11,14-Eicosatetraynoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
   -8.5589    1.5136    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8207    0.1897    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3577    0.4826    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3121    1.0186   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.3520   -1.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    0.1276   -1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303   -0.8736   -1.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.0895   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -1.8091   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -1.5593    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674   -1.2365    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.7545    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -2.1692   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3121   -2.6620   -0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843   -2.1014    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4319   -1.6272    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5651   -1.0391    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570    0.4658    1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2204    1.1485    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216    2.5992    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9912    3.0595    1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8670    3.4563   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8565    2.3627    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9956    1.6478   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3848    1.5953    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9471   -0.2571    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1983   -0.4537    0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7990   -0.4637    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154    1.1932    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2001   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9444    1.9052   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.8128   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4931    2.1411   -0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -2.8732   -0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.3985   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797   -1.5970    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -0.1257    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -3.7548   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3186   -2.2473   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7246   -1.5057    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4691   -1.1291    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1482    0.8893    2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    0.5655    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1452    0.9570   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708    0.7119   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3512    4.3317   -0.7101 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  3  0
  7  8  1  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
M  END


  Mrv1533004241520022D          

 22 21  0  0  0  0            999 V2000
  -10.9085    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1940    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4796    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7651    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0506    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  3  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252124

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC#CCC#CCC#CCC#CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)

> <INCHI_KEY>
MGLDCXPLYOWQRP-UHFFFAOYSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.41

> <EXACT_MASS>
296.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.30642681566094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
icosa-5,8,11,14-tetraynoic acid

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
6.373684096333333

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.083481277243657

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
92.93319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
icosa-5,8,11,14-tetraynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252124
     RDKit          3D
5,8,11,14-Eicosatetraynoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
   -8.5589    1.5136    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8207    0.1897    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3577    0.4826    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3121    1.0186   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.3520   -1.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    0.1276   -1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303   -0.8736   -1.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.0895   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -1.8091   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -1.5593    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674   -1.2365    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.7545    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -2.1692   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3121   -2.6620   -0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843   -2.1014    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4319   -1.6272    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5651   -1.0391    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570    0.4658    1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2204    1.1485    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216    2.5992    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9912    3.0595    1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8670    3.4563   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8565    2.3627    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9956    1.6478   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3848    1.5953    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9471   -0.2571    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1983   -0.4537    0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7990   -0.4637    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154    1.1932    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2001   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9444    1.9052   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.8128   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4931    2.1411   -0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -2.8732   -0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.3985   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797   -1.5970    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -0.1257    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -3.7548   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3186   -2.2473   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7246   -1.5057    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4691   -1.1291    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1482    0.8893    2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    0.5655    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1452    0.9570   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708    0.7119   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3512    4.3317   -0.7101 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  3  0
  7  8  1  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0     -20.363   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -19.029   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.695   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.362   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -15.028   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.694   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.360   0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.027  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.693   0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.359   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.358   0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.025  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.691   0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.977  -0.206   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    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0252124
HETATM    1  C1  UNL     1      -8.559   1.514   0.847  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.821   0.190   0.977  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.358   0.483   0.657  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.312   1.019  -0.741  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.905   1.352  -1.185  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.104   0.128  -1.127  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.430  -0.874  -1.065  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.595  -2.089  -0.973  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.357  -1.809  -0.216  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.349  -1.559   0.404  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.867  -1.236   1.156  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.069  -1.754   0.497  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.071  -2.169  -0.033  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.312  -2.662  -0.666  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.484  -2.101   0.030  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.432  -1.627   0.606  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.565  -1.039   1.311  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.357   0.466   1.498  1.00  0.00           C  
HETATM   19  C19 UNL     1       7.220   1.149   0.163  1.00  0.00           C  
HETATM   20  C20 UNL     1       7.022   2.599   0.398  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.991   3.059   1.567  1.00  0.00           O  
HETATM   22  O2  UNL     1       6.867   3.456  -0.708  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.856   2.363   1.079  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.996   1.648  -0.164  1.00  0.00           H  
HETATM   25  H3  UNL     1      -9.385   1.595   1.577  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.947  -0.257   1.966  1.00  0.00           H  
HETATM   27  H5  UNL     1      -8.198  -0.454   0.159  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.799  -0.464   0.779  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.915   1.193   1.396  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.664   0.200  -1.417  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.944   1.905  -0.816  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.911   1.813  -2.192  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.493   2.141  -0.497  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.130  -2.873  -0.427  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.344  -2.399  -2.012  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.780  -1.597   2.200  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.021  -0.126   1.235  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.389  -3.755  -0.640  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.319  -2.247  -1.690  1.00  0.00           H  
HETATM   40  H18 UNL     1       7.725  -1.506   2.300  1.00  0.00           H  
HETATM   41  H19 UNL     1       8.469  -1.129   0.658  1.00  0.00           H  
HETATM   42  H20 UNL     1       8.148   0.889   2.121  1.00  0.00           H  
HETATM   43  H21 UNL     1       6.396   0.565   2.061  1.00  0.00           H  
HETATM   44  H22 UNL     1       8.145   0.957  -0.422  1.00  0.00           H  
HETATM   45  H23 UNL     1       6.371   0.712  -0.405  1.00  0.00           H  
HETATM   46  H24 UNL     1       7.351   4.332  -0.710  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7    7
CONECT    7    8
CONECT    8    9   34   35
CONECT    9   10   10   10
CONECT   10   11
CONECT   11   12   36   37
CONECT   12   13   13   13
CONECT   13   14
CONECT   14   15   38   39
CONECT   15   16   16   16
CONECT   16   17
CONECT   17   18   40   41
CONECT   18   19   42   43
CONECT   19   20   44   45
CONECT   20   21   21   22
CONECT   22   46
END

HMDB0252124
     RDKit          3D
5,8,11,14-Eicosatetraynoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
   -8.5589    1.5136    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8207    0.1897    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3577    0.4826    0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3121    1.0186   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.3520   -1.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    0.1276   -1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303   -0.8736   -1.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.0895   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -1.8091   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -1.5593    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674   -1.2365    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.7545    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -2.1692   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3121   -2.6620   -0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843   -2.1014    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4319   -1.6272    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5651   -1.0391    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570    0.4658    1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2204    1.1485    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216    2.5992    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9912    3.0595    1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8670    3.4563   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8565    2.3627    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9956    1.6478   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3848    1.5953    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9471   -0.2571    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1983   -0.4537    0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7990   -0.4637    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9154    1.1932    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    0.2001   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9444    1.9052   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109    1.8128   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4931    2.1411   -0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -2.8732   -0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.3985   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797   -1.5970    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -0.1257    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -3.7548   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3186   -2.2473   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7246   -1.5057    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4691   -1.1291    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1482    0.8893    2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    0.5655    2.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1452    0.9570   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708    0.7119   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3512    4.3317   -0.7101 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  3  0
  7  8  1  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,8,11,14-Eicosatetraynoate	Generator
581114-Eicosatetraynoic acid	ChEMBL
581114-Eicosatetraynoate	Generator
Icosa-5,8,11,14-tetraynoate	Generator
5,8,11,14 Eicosatetraynoic acid	MeSH
5,8,11,14-Eicosatetraynoic acid	MeSH

Chemical Formula

C₂₀H₂₄O₂

Average Molecular Weight

296.41

Monoisotopic Molecular Weight

296.177630013

IUPAC Name

icosa-5,8,11,14-tetraynoic acid

Traditional Name

icosa-5,8,11,14-tetraynoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC#CCC#CCC#CCC#CCCCC(O)=O

InChI Identifier

InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)

InChI Key

MGLDCXPLYOWQRP-UHFFFAOYSA-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

Unsaturated fatty acids (LMFA01030691 )

Ontology

Not Available

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
logP	5.7	ALOGPS
logP	6.37	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.08	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	14	ChemAxon
Refractivity	92.93 m³·mol⁻¹	ChemAxon
Polarizability	37.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	162.233	30932474
DeepCCS	[M-H]-	159.217	30932474
DeepCCS	[M-2H]-	194.715	30932474
DeepCCS	[M+Na]+	170.941	30932474
AllCCS	[M+H]+	176.9	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	179.8	32859911
AllCCS	[M+Na]+	180.7	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	179.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,8,11,14-Eicosatetraynoic acid	CCCCCC#CCC#CCC#CCC#CCCCC(O)=O	3917.7	Standard polar	33892256
5,8,11,14-Eicosatetraynoic acid	CCCCCC#CCC#CCC#CCC#CCCCC(O)=O	2497.5	Standard non polar	33892256
5,8,11,14-Eicosatetraynoic acid	CCCCCC#CCC#CCC#CCC#CCCCC(O)=O	2544.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5,8,11,14-Eicosatetraynoic acid (HMDB0252124)

MOL for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

3D MOL for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

3D SDF for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

3D-SDF for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

PDB for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

3D PDB for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

SMILES for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

INCHI for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

Structure for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

3D Structure for HMDB0252124 (5,8,11,14-Eicosatetraynoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized