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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-16 22:27:00 UTC

Update Date

2022-03-07 02:51:03 UTC

HMDB ID

HMDB0011108

Secondary Accession Numbers

HMDB11108

Metabolite Identification

Common Name

17-Hydroxylinolenic acid

Description

17-Hydroxylinolenic acid is a hydroxylated (on the 17th carbon) version of alpha linolenic acid produced from alpha linolenic acid. Another isomer known as 2-hydroxylinolenic acid is also known to exist. Alpha-Linolenic acid is an organic compound found in many common vegetable oils. Systematically, it is named all-cis-9,12,15-octadecatrienoic acid (PMID:11413487 ). In physiological literature, it is given the name 18:3 (n−3). Alpha-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid (PMID: 19269799 ).

Structure

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

HMDB0011108
     RDKit          3D
17-Hydroxylinolenic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -5.7911   -1.3133   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7173   -2.0180   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2875   -3.2022   -1.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2534   -1.2010   -2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -0.1469   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    0.2218   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    1.5707   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    2.5407    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921    2.4149    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    2.7110    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    1.8574    2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    0.5460    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.2965    1.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    1.2968    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    1.1264    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.2368    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -0.4777   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687   -1.8183   -1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7334   -2.0047   -1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -1.0349   -1.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957   -3.2387   -1.7195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7973   -0.2485   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080   -1.4095    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739   -1.7151   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -2.4033   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1027   -3.4192   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5606   -1.4773   -3.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1324    0.4605   -2.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.5282    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.0819   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.7879   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640    3.5118    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293    3.3223   -0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    1.5798   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    3.7249    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    2.1336    3.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.1548    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.1822    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    0.3769    3.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295   -0.7326    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310    1.2239    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1711    2.3466    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970    1.9169    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741    1.2864    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.0514    1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -0.3170    0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.5076   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    0.3356   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -2.0734   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997   -2.6174   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -3.4506   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

  Mrv0541 02241201192D          

 21 20  0  0  0  0            999 V2000
   11.3554   -6.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6408   -6.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9257   -6.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2110   -6.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0701   -6.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7852   -6.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4999   -6.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2142   -6.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9288   -6.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6431   -6.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3577   -6.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0720   -6.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7867   -6.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5009   -6.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2156   -6.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9299   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6446   -6.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3588   -6.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0735   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3448   -7.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9323   -5.6844    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
  1  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  3 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011108

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h2-3,7,9,13,15,17,19H,4-6,8,10-12,14,16H2,1H3,(H,20,21)/b3-2-,9-7-,15-13-

> <INCHI_KEY>
PSQSSLVXOIJSMX-XAFOFORCSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.845375165083375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z,15Z)-17-hydroxyoctadeca-9,12,15-trienoic acid

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
4.751190340666667

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.00569479287329

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167337373527

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9215091510669424

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.2279

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxylinolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011108
     RDKit          3D
17-Hydroxylinolenic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -5.7911   -1.3133   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7173   -2.0180   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2875   -3.2022   -1.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2534   -1.2010   -2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -0.1469   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    0.2218   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    1.5707   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    2.5407    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921    2.4149    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    2.7110    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    1.8574    2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    0.5460    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.2965    1.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    1.2968    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    1.1264    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.2368    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -0.4777   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687   -1.8183   -1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7334   -2.0047   -1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -1.0349   -1.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957   -3.2387   -1.7195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7973   -0.2485   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080   -1.4095    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739   -1.7151   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -2.4033   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1027   -3.4192   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5606   -1.4773   -3.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1324    0.4605   -2.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.5282    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.0819   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.7879   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640    3.5118    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293    3.3223   -0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    1.5798   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    3.7249    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    2.1336    3.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.1548    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.1822    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    0.3769    3.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295   -0.7326    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310    1.2239    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1711    2.3466    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970    1.9169    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741    1.2864    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.0514    1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -0.3170    0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.5076   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    0.3356   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -2.0734   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997   -2.6174   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -3.4506   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.197 -11.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.863 -12.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.528 -11.835   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      17.194 -12.604   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.531 -12.604   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.866 -11.835   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.200 -12.604   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.533 -11.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.867 -12.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.200 -11.833   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.534 -11.835   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.868 -12.606   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.202 -11.837   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.535 -11.831   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.869 -12.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.202 -11.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.537 -11.837   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.870 -12.607   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.204 -11.838   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      39.844 -14.113   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      18.540 -10.611   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3                                                            
CONECT    5    1    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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0011108
HETATM    1  C1  UNL     1      -5.791  -1.313  -0.158  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.717  -2.018  -0.930  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.288  -3.202  -1.469  1.00  0.00           O  
HETATM    4  C3  UNL     1      -4.253  -1.201  -2.078  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.479  -0.147  -1.901  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.068   0.222  -0.501  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.506   1.571  -0.140  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.688   2.541   0.208  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.192   2.415   0.286  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.805   2.711   1.653  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.172   1.857   2.401  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.200   0.546   1.943  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.709   0.297   1.977  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.396   1.297   1.096  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.884   1.126   1.080  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.319  -0.237   0.583  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.829  -0.478  -0.818  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.269  -1.818  -1.292  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.733  -2.005  -1.376  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.488  -1.035  -1.135  1.00  0.00           O  
HETATM   21  O3  UNL     1       6.296  -3.239  -1.719  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.797  -0.249  -0.458  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.608  -1.409   0.938  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.774  -1.715  -0.454  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.882  -2.403  -0.302  1.00  0.00           H  
HETATM   26  H5  UNL     1      -6.103  -3.419  -0.984  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.561  -1.477  -3.097  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.132   0.461  -2.745  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.497  -0.528   0.228  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.997   0.082  -0.457  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.591   1.788  -0.160  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.164   3.512   0.455  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.829   3.322  -0.322  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.778   1.580  -0.231  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.088   3.725   2.021  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.097   2.134   3.431  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.156   0.155   1.011  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.194  -0.182   2.725  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.121   0.377   3.003  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.930  -0.733   1.628  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.031   1.224   0.039  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.171   2.347   1.415  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.297   1.917   0.420  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.274   1.286   2.112  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.865  -1.051   1.202  1.00  0.00           H  
HETATM   46  H25 UNL     1       5.421  -0.317   0.705  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.702  -0.508  -0.740  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.136   0.336  -1.506  1.00  0.00           H  
HETATM   49  H28 UNL     1       3.820  -2.073  -2.293  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.900  -2.617  -0.609  1.00  0.00           H  
HETATM   51  H30 UNL     1       7.227  -3.451  -1.439  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   25
CONECT    3   26
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7   29   30
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   33   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   20   20   21
CONECT   21   51
END

HMDB0011108
     RDKit          3D
17-Hydroxylinolenic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -5.7911   -1.3133   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7173   -2.0180   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2875   -3.2022   -1.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2534   -1.2010   -2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -0.1469   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    0.2218   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    1.5707   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    2.5407    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921    2.4149    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    2.7110    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    1.8574    2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    0.5460    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.2965    1.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    1.2968    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    1.1264    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.2368    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -0.4777   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687   -1.8183   -1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7334   -2.0047   -1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -1.0349   -1.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957   -3.2387   -1.7195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7973   -0.2485   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080   -1.4095    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739   -1.7151   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -2.4033   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1027   -3.4192   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5606   -1.4773   -3.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1324    0.4605   -2.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.5282    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.0819   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.7879   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1640    3.5118    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293    3.3223   -0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    1.5798   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    3.7249    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    2.1336    3.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.1548    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.1822    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    0.3769    3.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295   -0.7326    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310    1.2239    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1711    2.3466    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970    1.9169    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741    1.2864    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646   -1.0514    1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205   -0.3170    0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.5076   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    0.3356   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -2.0734   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997   -2.6174   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -3.4506   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,12Z,15Z)-17-Hydroxyoctadecatri-9,12,15-enoic acid	Kegg
(9Z,12Z,15Z)-17-Hydroxyoctadecatri-9,12,15-enoate	Generator
17-Hydroxylinolenate	Generator
(9Z,12Z,15Z)-17-Hydroxyoctadeca-9,12,15-trienoate	HMDB

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

(9Z,12Z,15Z)-17-hydroxyoctadeca-9,12,15-trienoic acid

Traditional Name

17-hydroxylinolenic acid

CAS Registry Number

Not Available

SMILES

CC(O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h2-3,7,9,13,15,17,19H,4-6,8,10-12,14,16H2,1H3,(H,20,21)/b3-2-,9-7-,15-13-

InChI Key

PSQSSLVXOIJSMX-XAFOFORCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lipid (CHEBI:80463 )
Other Octadecanoids (C16346 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011108)
Membrane (HMDB: HMDB0011108)

Source

Exogenous

Exogenous (HMDB: HMDB0011108)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011108)

Process

Not Available

Role

Not Available

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	0.0038 g/L	ALOGPS
logP	5.47	ALOGPS
logP	4.75	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	91.23 m³·mol⁻¹	ChemAxon
Polarizability	35.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	181.319	31661259
DarkChem	[M-H]-	178.022	31661259
DeepCCS	[M+H]+	174.365	30932474
DeepCCS	[M-H]-	172.007	30932474
DeepCCS	[M-2H]-	204.893	30932474
DeepCCS	[M+Na]+	180.458	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	175.7	32859911
AllCCS	[M+NH4]+	181.5	32859911
AllCCS	[M+Na]+	182.4	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	182.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17-Hydroxylinolenic acid	CC(O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	3811.2	Standard polar	33892256
17-Hydroxylinolenic acid	CC(O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	2161.7	Standard non polar	33892256
17-Hydroxylinolenic acid	CC(O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	2334.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17-Hydroxylinolenic acid,1TMS,isomer #1	CC(/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C	2517.1	Semi standard non polar	33892256
17-Hydroxylinolenic acid,1TMS,isomer #2	CC(O)/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2421.8	Semi standard non polar	33892256
17-Hydroxylinolenic acid,2TMS,isomer #1	CC(/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2479.8	Semi standard non polar	33892256
17-Hydroxylinolenic acid,1TBDMS,isomer #1	CC(/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2757.0	Semi standard non polar	33892256
17-Hydroxylinolenic acid,1TBDMS,isomer #2	CC(O)/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2667.5	Semi standard non polar	33892256
17-Hydroxylinolenic acid,2TBDMS,isomer #1	CC(/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2945.4	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 - 17-Hydroxylinolenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5590000000-8f28c5dae453817d7dfb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Hydroxylinolenic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9664400000-ac81b873936cd0141936	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Hydroxylinolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 10V, Positive-QTOF	splash10-056r-0090000000-b1a052a3f0037b1df149	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 20V, Positive-QTOF	splash10-057j-0190000000-3bd32795337b7cce90e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 40V, Positive-QTOF	splash10-014l-7960000000-81bc8731572da2e954e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 10V, Negative-QTOF	splash10-0006-0090000000-d7d7eb631ae15d19ced0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 20V, Negative-QTOF	splash10-004l-0090000000-037e45733d4f0e1ed2d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 40V, Negative-QTOF	splash10-0a4i-9160000000-9160763ac1fa572ec61d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 10V, Negative-QTOF	splash10-0006-0090000000-e1c3460065b446c87c51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 20V, Negative-QTOF	splash10-004l-1090000000-5208257639b7da19e6fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 40V, Negative-QTOF	splash10-0006-9420000000-2ebbcc0ca8582af1a7e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 10V, Positive-QTOF	splash10-004j-1590000000-b1b718820e23aa7022a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 20V, Positive-QTOF	splash10-0a59-4920000000-c32ab2d6109e3d596377	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Hydroxylinolenic acid 40V, Positive-QTOF	splash10-017l-9600000000-59b25a1b0624f1fba610	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027891

KNApSAcK ID

Not Available

Chemspider ID

8884298

KEGG Compound ID

C16346

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10708957

PDB ID

Not Available

ChEBI ID

80463

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Brenna JT, Salem N Jr, Sinclair AJ, Cunnane SC: alpha-Linolenic acid supplementation and conversion to n-3 long-chain polyunsaturated fatty acids in humans. Prostaglandins Leukot Essent Fatty Acids. 2009 Feb-Mar;80(2-3):85-91. doi: 10.1016/j.plefa.2009.01.004. Epub 2009 Mar 9. [PubMed:19269799 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 17-Hydroxylinolenic acid (HMDB0011108)

MOL for HMDB0011108 (17-Hydroxylinolenic acid)

3D MOL for HMDB0011108 (17-Hydroxylinolenic acid)

3D SDF for HMDB0011108 (17-Hydroxylinolenic acid)

3D-SDF for HMDB0011108 (17-Hydroxylinolenic acid)

PDB for HMDB0011108 (17-Hydroxylinolenic acid)

3D PDB for HMDB0011108 (17-Hydroxylinolenic acid)

SMILES for HMDB0011108 (17-Hydroxylinolenic acid)

INCHI for HMDB0011108 (17-Hydroxylinolenic acid)

Structure for HMDB0011108 (17-Hydroxylinolenic acid)

3D Structure for HMDB0011108 (17-Hydroxylinolenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra