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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:52:53 UTC

Update Date

2021-09-26 22:56:12 UTC

HMDB ID

HMDB0246870

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,8,11-Eicosatriynoic acid

Description

5,8,11-Eicosatriynoic acid, also known as 5,8,11-eti or eicosa-5,8,11-triinsaeure, 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. Based on a literature review a significant number of articles have been published on 5,8,11-Eicosatriynoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,8,11-eicosatriynoic 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-Eicosatriynoic 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

HMDB0246870
     RDKit          3D
5,8,11-Eicosatriynoic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.7284   -0.1756    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7104    0.9502    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0816    0.6692    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -0.5784    2.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262   -0.8581    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971   -0.5804    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040    0.8714   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.1094   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613    0.3403   -1.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -0.2975   -2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -1.0738   -2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -1.0037   -1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2063   -0.9550   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324   -0.8982    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833   -0.1844   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184    0.3884   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434    1.0756   -1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5925    1.2697   -0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1219   -0.0265    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2443    0.2127    1.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5966    1.3969    1.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9208   -0.8160    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1761   -1.0829    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3845   -0.3139    1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3113    0.2247   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.9913   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3622    1.8664    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4712    1.5723    2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9512    0.6818    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0531   -1.4365    1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2329   -0.8109    3.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.4689    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -2.0031    1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -1.1196   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894   -1.0035   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    1.0521    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0195    1.5335    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.7890   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141    2.1886   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.6923   -3.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -2.1179   -2.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624   -1.8992    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247   -0.3804    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7637    0.4382   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244    2.0649   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1530    1.8190    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.9350   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.5800    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5132   -0.6057   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8937   -0.6992    1.8447 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  1  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
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
M  END


  Mrv1652309112101532D          

 22 21  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1440    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8585    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2874    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730    2.1434    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  1  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>
HMDB0246870

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-8,11,14,17-19H2,1H3,(H,21,22)

> <INCHI_KEY>
OWYNLPMPYBYKJP-UHFFFAOYSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.33628198307056

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
icosa-5,8,11-triynoic acid

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
6.788977431666666

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.083482510748583

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.5718

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8,11-eicosatriynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246870
     RDKit          3D
5,8,11-Eicosatriynoic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.7284   -0.1756    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7104    0.9502    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0816    0.6692    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -0.5784    2.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262   -0.8581    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971   -0.5804    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040    0.8714   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.1094   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613    0.3403   -1.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -0.2975   -2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -1.0738   -2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -1.0037   -1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2063   -0.9550   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324   -0.8982    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833   -0.1844   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184    0.3884   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434    1.0756   -1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5925    1.2697   -0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1219   -0.0265    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2443    0.2127    1.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5966    1.3969    1.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9208   -0.8160    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1761   -1.0829    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3845   -0.3139    1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3113    0.2247   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.9913   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3622    1.8664    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4712    1.5723    2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9512    0.6818    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0531   -1.4365    1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2329   -0.8109    3.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.4689    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -2.0031    1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -1.1196   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894   -1.0035   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    1.0521    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0195    1.5335    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.7890   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141    2.1886   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.6923   -3.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -2.1179   -2.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624   -1.8992    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247   -0.3804    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7637    0.4382   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244    2.0649   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1530    1.8190    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.9350   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.5800    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5132   -0.6057   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8937   -0.6992    1.8447 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  1  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
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.599   5.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.933   6.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.267   5.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.600   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.934   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.268   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.602   5.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.935   6.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.269   5.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.603   6.311   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.936   5.541   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      32.270   6.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      30.936   4.001   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    HMDB0246870
HETATM    1  C1  UNL     1      -7.728  -0.176   0.304  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.710   0.950   0.627  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.082   0.669   1.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.327  -0.578   2.035  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.026  -0.858   1.478  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.597  -0.580   0.105  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.304   0.871  -0.171  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.942   1.109  -1.623  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.761   0.340  -1.974  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.786  -0.297  -2.286  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.372  -1.074  -2.676  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.366  -1.004  -1.602  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.206  -0.955  -0.721  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.232  -0.898   0.321  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.383  -0.184  -0.276  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.318   0.388  -0.781  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.443   1.076  -1.415  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.593   1.270  -0.451  1.00  0.00           C  
HETATM   19  C19 UNL     1       8.122  -0.027   0.078  1.00  0.00           C  
HETATM   20  C20 UNL     1       9.244   0.213   1.016  1.00  0.00           C  
HETATM   21  O1  UNL     1       9.597   1.397   1.242  1.00  0.00           O  
HETATM   22  O2  UNL     1       9.921  -0.816   1.654  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.176  -1.083   0.052  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.385  -0.314   1.189  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.311   0.225  -0.561  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.074   0.991  -0.235  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.362   1.866   0.659  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.471   1.572   2.284  1.00  0.00           H  
HETATM   29  H7  UNL     1      -6.951   0.682   2.696  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.053  -1.436   1.727  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.233  -0.811   3.179  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.188  -0.469   2.175  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.852  -2.003   1.646  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.625  -1.120  -0.135  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.289  -1.004  -0.678  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.308   1.052   0.411  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.019   1.534   0.254  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.825   0.789  -2.234  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.814   2.189  -1.773  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.851  -0.692  -3.607  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.053  -2.118  -2.843  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.562  -1.899   0.639  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.825  -0.380   1.192  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.764   0.438  -2.283  1.00  0.00           H  
HETATM   45  H23 UNL     1       6.124   2.065  -1.780  1.00  0.00           H  
HETATM   46  H24 UNL     1       7.153   1.819   0.433  1.00  0.00           H  
HETATM   47  H25 UNL     1       8.366   1.935  -0.853  1.00  0.00           H  
HETATM   48  H26 UNL     1       7.300  -0.580   0.570  1.00  0.00           H  
HETATM   49  H27 UNL     1       8.513  -0.606  -0.803  1.00  0.00           H  
HETATM   50  H28 UNL     1      10.894  -0.699   1.845  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   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   10   10
CONECT   10   11
CONECT   11   12   40   41
CONECT   12   13   13   13
CONECT   13   14
CONECT   14   15   42   43
CONECT   15   16   16   16
CONECT   16   17
CONECT   17   18   44   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   21   22
CONECT   22   50
END

HMDB0246870
     RDKit          3D
5,8,11-Eicosatriynoic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -7.7284   -0.1756    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7104    0.9502    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0816    0.6692    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -0.5784    2.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262   -0.8581    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971   -0.5804    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040    0.8714   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.1094   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613    0.3403   -1.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -0.2975   -2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -1.0738   -2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -1.0037   -1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2063   -0.9550   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324   -0.8982    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833   -0.1844   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184    0.3884   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434    1.0756   -1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5925    1.2697   -0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1219   -0.0265    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2443    0.2127    1.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5966    1.3969    1.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9208   -0.8160    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1761   -1.0829    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3845   -0.3139    1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3113    0.2247   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.9913   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3622    1.8664    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4712    1.5723    2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9512    0.6818    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0531   -1.4365    1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2329   -0.8109    3.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.4689    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -2.0031    1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -1.1196   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2894   -1.0035   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    1.0521    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0195    1.5335    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.7890   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141    2.1886   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.6923   -3.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -2.1179   -2.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624   -1.8992    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247   -0.3804    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7637    0.4382   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244    2.0649   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1530    1.8190    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.9350   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.5800    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5132   -0.6057   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8937   -0.6992    1.8447 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  1  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
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,8,11-Eicosatriyenoic acid	ChEBI
5,8,11-ETI	ChEBI
Eicosa-5,8,11-triinsaeure	ChEBI
ETI	ChEBI
5,8,11-Eicosatriyenoate	Generator
5,8,11-Eicosatriynoate	Generator
5,8,11-Icosatriynoate	HMDB
5,8,11-Eicosatriynoic acid	ChEBI

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.442

Monoisotopic Molecular Weight

300.208930142

IUPAC Name

icosa-5,8,11-triynoic acid

Traditional Name

5,8,11-eicosatriynoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC#CCC#CCC#CCCCC(O)=O

InChI Identifier

InChI=1S/C20H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-8,11,14,17-19H2,1H3,(H,21,22)

InChI Key

OWYNLPMPYBYKJP-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

long-chain fatty acid (CHEBI:53454 )
icosanoid (CHEBI:53454 )
polyunsaturated fatty acid (CHEBI:53454 )
acetylenic fatty acid (CHEBI:53454 )
Unsaturated fatty acids (LMFA01030696 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

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	6.21	ALOGPS
logP	6.79	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	15	ChemAxon
Refractivity	93.57 m³·mol⁻¹	ChemAxon
Polarizability	38.34 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]+	169.443	30932474
DeepCCS	[M-H]-	165.516	30932474
DeepCCS	[M-2H]-	202.254	30932474
DeepCCS	[M+Na]+	178.258	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.4	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	184.1	32859911
AllCCS	[M+HCOO]-	185.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	25.5037 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3474.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	798.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	321.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	492.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	583.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1218.6 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	1272.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	323.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2233.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	670.3 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	2244.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	836.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	887.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	806.4 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	37.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,8,11-Eicosatriynoic acid	CCCCCCCCC#CCC#CCC#CCCCC(O)=O	3803.8	Standard polar	33892256
5,8,11-Eicosatriynoic acid	CCCCCCCCC#CCC#CCC#CCCCC(O)=O	2430.1	Standard non polar	33892256
5,8,11-Eicosatriynoic acid	CCCCCCCCC#CCC#CCC#CCCCC(O)=O	2490.9	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 - 5,8,11-Eicosatriynoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9060000000-04363b95d9e13953a411	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8,11-Eicosatriynoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8,11-Eicosatriynoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8,11-Eicosatriynoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 5,8,11-Eicosatriynoic acid 10V, Positive-QTOF	splash10-0ue9-2495000000-040b0b23db88f1619526	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatriynoic acid 20V, Positive-QTOF	splash10-00su-4920000000-611c94b533cd756da3f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatriynoic acid 40V, Positive-QTOF	splash10-004r-8900000000-9a13e10bdf3d0862f048	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatriynoic acid 10V, Negative-QTOF	splash10-0002-0090000000-2508ee2ed1a3abdc24de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatriynoic acid 20V, Negative-QTOF	splash10-000t-2390000000-d33632161d8b0f5dbe9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatriynoic acid 40V, Negative-QTOF	splash10-00kf-9630000000-cbdb86c11912e9922302	2021-10-12	Wishart Lab	View Spectrum

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

1716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1781

PDB ID

Not Available

ChEBI ID

53454

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-Eicosatriynoic acid (HMDB0246870)

MOL for HMDB0246870 (5,8,11-Eicosatriynoic acid)

3D MOL for HMDB0246870 (5,8,11-Eicosatriynoic acid)

3D SDF for HMDB0246870 (5,8,11-Eicosatriynoic acid)

3D-SDF for HMDB0246870 (5,8,11-Eicosatriynoic acid)

PDB for HMDB0246870 (5,8,11-Eicosatriynoic acid)

3D PDB for HMDB0246870 (5,8,11-Eicosatriynoic acid)

SMILES for HMDB0246870 (5,8,11-Eicosatriynoic acid)

INCHI for HMDB0246870 (5,8,11-Eicosatriynoic acid)

Structure for HMDB0246870 (5,8,11-Eicosatriynoic acid)

3D Structure for HMDB0246870 (5,8,11-Eicosatriynoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra