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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 15:30:04 UTC

Update Date

2022-09-22 17:43:55 UTC

HMDB ID

HMDB0006547

Secondary Accession Numbers

HMDB06547

Metabolite Identification

Common Name

Stearidonic acid

Description

Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404 ). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716 ).

Structure

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

HMDB0006547
     RDKit          3D
Stearidonic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -7.6311    2.3583    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0234    1.0241   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4688    0.3523    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2092    0.0513    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    0.3545   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6322   -0.9309   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -1.2066   -0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -0.2712    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    0.0014   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -0.2594   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.8497    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -2.1277    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -2.3567    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -1.4373    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078   -1.1655   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3588   -0.2236    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723    1.1264    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.7693   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.4745   -0.6972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995    2.6770   -1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7836    2.9920   -0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9550    2.8688    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5789    2.1644    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607    1.1152   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9585    0.4301   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779    0.0900    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -0.4492    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    1.1493    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739    0.7656   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -1.6508   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -2.1722   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645   -0.7344    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    0.6808    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    0.4493   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923   -0.0462   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -0.0834    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.0912    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.8379   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -3.3317   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8436   -1.9935    1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419   -0.4669    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7372   -2.1320   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.7293   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0725   -0.0794   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9422   -0.7373    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891    1.7330    0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994    1.0911    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9048    2.6452   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END


  Mrv1652303202019002D          

 20 19  0  0  0  0            999 V2000
   19.2651   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5506   -9.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8361   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1216   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4070   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6925   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9779   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2634   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5489   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8343   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1198   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4053   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6907   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9762   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2617   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8326   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   -8.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4035   -9.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006547

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

> <INCHI_KEY>
JIWBIWFOSCKQMA-LTKCOYKYSA-N

> <FORMULA>
C18H28O2

> <MOLECULAR_WEIGHT>
276.4137

> <EXACT_MASS>
276.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.10997676136738

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

> <ALOGPS_LOGP>
6.19

> <JCHEM_LOGP>
5.698033481

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922492763245736

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.752

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stearidonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006547
     RDKit          3D
Stearidonic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -7.6311    2.3583    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0234    1.0241   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4688    0.3523    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2092    0.0513    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    0.3545   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6322   -0.9309   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -1.2066   -0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -0.2712    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    0.0014   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -0.2594   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.8497    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -2.1277    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -2.3567    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -1.4373    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078   -1.1655   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3588   -0.2236    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723    1.1264    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.7693   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.4745   -0.6972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995    2.6770   -1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7836    2.9920   -0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9550    2.8688    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5789    2.1644    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607    1.1152   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9585    0.4301   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779    0.0900    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -0.4492    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    1.1493    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739    0.7656   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -1.6508   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -2.1722   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645   -0.7344    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    0.6808    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    0.4493   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923   -0.0462   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -0.0834    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.0912    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.8379   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -3.3317   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8436   -1.9935    1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419   -0.4669    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7372   -2.1320   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.7293   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0725   -0.0794   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9422   -0.7373    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891    1.7330    0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994    1.0911    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9048    2.6452   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      35.962 -17.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.628 -16.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.294 -17.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.960 -17.681   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.626 -16.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.293 -17.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.959 -17.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.625 -16.911   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.291 -17.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.957 -17.681   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.624 -16.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.290 -17.681   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.956 -17.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.622 -16.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.288 -17.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.955 -16.911   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.621 -17.681   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.287 -16.911   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.287 -15.371   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.953 -17.681   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0006547
HETATM    1  C1  UNL     1      -7.631   2.358   0.205  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.023   1.024  -0.254  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.469   0.352   0.914  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.209   0.051   1.019  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.211   0.355  -0.025  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.632  -0.931  -0.442  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.375  -1.207  -0.323  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.399  -0.271   0.241  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.396   0.001  -0.809  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.856  -0.259  -0.655  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.421  -0.850   0.566  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.053  -2.128   0.152  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.302  -2.357   0.323  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.239  -1.437   0.923  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.308  -1.166  -0.161  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.359  -0.224   0.315  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.872   1.126   0.721  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.218   1.769  -0.434  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.034   1.474  -0.697  1.00  0.00           O  
HETATM   20  O2  UNL     1       5.900   2.677  -1.208  1.00  0.00           O  
HETATM   21  H1  UNL     1      -7.784   2.992  -0.671  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.955   2.869   0.915  1.00  0.00           H  
HETATM   23  H3  UNL     1      -8.579   2.164   0.783  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.461   1.115  -1.155  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.959   0.430  -0.565  1.00  0.00           H  
HETATM   26  H6  UNL     1      -7.178   0.090   1.752  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.845  -0.449   1.908  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.520   1.149   0.264  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.674   0.766  -0.979  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.363  -1.651  -0.871  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.007  -2.172  -0.650  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.965  -0.734   1.179  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.820   0.681   0.654  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.800   0.449  -1.745  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.592  -0.046  -1.458  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.130  -0.083   0.945  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.761  -1.091   1.384  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.336  -2.838  -0.310  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.701  -3.332  -0.011  1.00  0.00           H  
HETATM   40  H20 UNL     1       4.844  -1.994   1.716  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.942  -0.467   1.260  1.00  0.00           H  
HETATM   42  H22 UNL     1       5.737  -2.132  -0.425  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.741  -0.729  -1.019  1.00  0.00           H  
HETATM   44  H24 UNL     1       7.073  -0.079  -0.528  1.00  0.00           H  
HETATM   45  H25 UNL     1       6.942  -0.737   1.108  1.00  0.00           H  
HETATM   46  H26 UNL     1       6.789   1.733   0.963  1.00  0.00           H  
HETATM   47  H27 UNL     1       5.199   1.091   1.608  1.00  0.00           H  
HETATM   48  H28 UNL     1       6.905   2.645  -1.369  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   19   20
CONECT   20   48
END

HMDB0006547
     RDKit          3D
Stearidonic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -7.6311    2.3583    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0234    1.0241   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4688    0.3523    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2092    0.0513    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    0.3545   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6322   -0.9309   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -1.2066   -0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -0.2712    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    0.0014   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -0.2594   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.8497    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -2.1277    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -2.3567    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -1.4373    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078   -1.1655   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3588   -0.2236    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723    1.1264    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.7693   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.4745   -0.6972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995    2.6770   -1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7836    2.9920   -0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9550    2.8688    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5789    2.1644    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607    1.1152   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9585    0.4301   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779    0.0900    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -0.4492    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195    1.1493    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739    0.7656   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -1.6508   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -2.1722   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645   -0.7344    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    0.6808    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    0.4493   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923   -0.0462   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -0.0834    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.0912    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.8379   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -3.3317   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8436   -1.9935    1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419   -0.4669    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7372   -2.1320   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.7293   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0725   -0.0794   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9422   -0.7373    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891    1.7330    0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994    1.0911    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9048    2.6452   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid	ChEBI
6,9,12,15-Octadecatetraenoic acid	ChEBI
SDA	ChEBI
6Z,9Z,12Z,15Z-Octadecatetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadecatetraenoate	Generator
6,9,12,15-Octadecatetraenoate	Generator
6Z,9Z,12Z,15Z-Octadecatetraenoate	Generator
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoate	Generator
Stearidonate	Generator
Stearidonic acid C18:4	HMDB
FA(18:4(6Z,9Z,12Z,15Z))	HMDB
FA(18:4n3)	HMDB
Moroctic acid	HMDB

Chemical Formula

C₁₈H₂₈O₂

Average Molecular Weight

276.4137

Monoisotopic Molecular Weight

276.20893014

IUPAC Name

(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

Traditional Name

stearidonic acid

CAS Registry Number

20290-75-9

SMILES

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

InChI Identifier

InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

InChI Key

JIWBIWFOSCKQMA-LTKCOYKYSA-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
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:32389 )
omega-3 fatty acid (CHEBI:32389 )
octadecatetraenoic acid (CHEBI:32389 )
Polyunsaturated fatty acids (C16300 )
Unsaturated fatty acids (LMFA01030357 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	382.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.037 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.890 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0005 g/L	ALOGPS
logP	6.19	ALOGPS
logP	5.7	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.92	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	12	ChemAxon
Refractivity	90.75 m³·mol⁻¹	ChemAxon
Polarizability	33.11 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
DarkChem	[M+H]+	176.678	31661259
DarkChem	[M-H]-	174.749	31661259
DeepCCS	[M+H]+	171.077	30932474
DeepCCS	[M-H]-	168.719	30932474
DeepCCS	[M-2H]-	201.605	30932474
DeepCCS	[M+Na]+	177.17	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.5	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	175.9	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.29 minutes	32390414
Predicted by Siyang on May 30, 2022	24.1855 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2987.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	573.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	239.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	455.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	682.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1123.1 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	620.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	87.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2200.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	762.0 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	1831.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	831.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	531.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	564.7 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Stearidonic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O	3524.8	Standard polar	33892256
Stearidonic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O	1970.7	Standard non polar	33892256
Stearidonic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O	2134.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Stearidonic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C	2188.5	Semi standard non polar	33892256
Stearidonic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C	2430.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Stearidonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9880000000-55228cb6c3a06a2fc9e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stearidonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9542000000-21c2332ba73d69ef8c6a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stearidonic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid LC-ESI-IT , negative-QTOF	splash10-001i-0190000000-adcd1a052c188cb4e292	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 6V, positive-QTOF	splash10-004i-0090000000-a5d727e64a76416e19b9	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 8V, positive-QTOF	splash10-004i-1590000000-c31b6670486c2add8842	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 12V, positive-QTOF	splash10-05ce-5920000000-97739d72e096d14b3173	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 14V, positive-QTOF	splash10-06gm-9800000000-e3ef89b4b4086a02043d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 19V, positive-QTOF	splash10-05ox-9300000000-e97626343f7e356e1b0c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 24V, positive-QTOF	splash10-05ox-9100000000-7d26fa860a4f5a50b573	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 28V, positive-QTOF	splash10-05r3-9100000000-c0fda9d6244f70011335	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 33V, positive-QTOF	splash10-05r3-9000000000-05ef38b3be958b95c066	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 39V, positive-QTOF	splash10-05r3-9000000000-0e7f4cff743f21c96f9d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 45V, positive-QTOF	splash10-0v03-9000000000-1e7762f073fff0bbf25f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid Orbitrap 54V, positive-QTOF	splash10-0udi-9000000000-e29ae2d32138f06d4b67	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-08fs-0940000000-3ce59c1bcc6c938f80dd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-05gl-6900000000-e7b111913bb0b52b7732	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-004i-9000000000-829ac26a60349ce7dc65	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-00di-3900000000-d5e9c06ac391b2ed266c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-0006-9000000000-4afb061d75b952ae6397	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-0006-0890000000-2c1d0ecbce6768af6a66	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOF	splash10-0072-0900000000-d1bd13cfc0f04540d631	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 10V, Positive-QTOF	splash10-056r-0190000000-db9d40fa02eaf6622425	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 20V, Positive-QTOF	splash10-05q9-4890000000-dacdea1487478325e7aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 40V, Positive-QTOF	splash10-069c-8930000000-57d8480196e2c8c76857	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 10V, Negative-QTOF	splash10-004i-0090000000-098cf1c00cd595f3355a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 20V, Negative-QTOF	splash10-0059-1090000000-74f3f2bf4ec73b4c1454	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stearidonic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-0bbf081c20a1f61dd3a1	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.016 +/- 0.001 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.408 +/- 0.4 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

5312508

PDB ID

Not Available

ChEBI ID

32389

Food Biomarker Ontology

Not Available

VMH ID

STRDNC

MarkerDB ID

Not Available

Good Scents ID

rw1680171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Miles EA, Banerjee T, Calder PC: The influence of different combinations of gamma-linolenic, stearidonic and eicosapentaenoic acids on the fatty acid composition of blood lipids and mononuclear cells in human volunteers. Prostaglandins Leukot Essent Fatty Acids. 2004 Jun;70(6):529-38. [PubMed:15120716 ]
Surette ME, Edens M, Chilton FH, Tramposch KM: Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. J Nutr. 2004 Jun;134(6):1406-11. [PubMed:15173404 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Fatty acid desaturase 2

General function:: Involved in heme binding
Specific function:: Component of a lipid metabolic pathway that catalyzes biosynthesis of highly unsaturated fatty acids (HUFA) from precursor essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3). Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma- linoleic acid (GLA) (18:3n-6) and stearidonic acid (18:4n-3) respectively and other desaturation steps. Highly unsaturated fatty acids (HUFA) play pivotal roles in many biological functions. It catalizes as well the introduction of a cis double bond in palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum
Gene Name:: FADS2
Uniprot ID:: O95864
Molecular weight:: 52259.1

Showing metabocard for Stearidonic acid (HMDB0006547)

MOL for HMDB0006547 (Stearidonic acid)

3D MOL for HMDB0006547 (Stearidonic acid)

3D SDF for HMDB0006547 (Stearidonic acid)

3D-SDF for HMDB0006547 (Stearidonic acid)

PDB for HMDB0006547 (Stearidonic acid)

3D PDB for HMDB0006547 (Stearidonic acid)

SMILES for HMDB0006547 (Stearidonic acid)

INCHI for HMDB0006547 (Stearidonic acid)

Structure for HMDB0006547 (Stearidonic acid)

3D Structure for HMDB0006547 (Stearidonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes