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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:41:51 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062290

Secondary Accession Numbers

HMDB62290

Metabolite Identification

Common Name

12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid

Description

12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid, also known as 12(R)DH-HETE, is classified as a member of the Hydroxyeicosatrienoic acids. Hydroxyeicosatrienoic acids are eicosanoic acids with an attached hydroxyl group and three CC double bonds. 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid is considered to be practically insoluble (in water) and acidic. 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid is an eicosanoid lipid molecule

Structure

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


  Mrv1652303161704412D          

 30 29  0  0  1  0            999 V2000
   -5.1927    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3349    2.7770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   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
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0062290
     RDKit          3D
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
   -7.6407    0.3807    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1404   -0.2988    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931   -0.8552   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2717    0.0604   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2477    0.7507   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -0.2088    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0441   -0.2961    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.6078   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3687    0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5412    2.2119   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    0.4808    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5120    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2863    0.0946   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -0.0892   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611   -0.8910    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.0338    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4867   -0.0964    1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -1.2005    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2246   -0.7198   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2518    0.1802    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2038    0.6104   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1535    1.3679   -0.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0767    0.1929   -2.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663    0.0050    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3187    0.1216    2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6776    1.4983    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8179   -1.1489    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8837    0.4202   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -1.5335   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -1.6193    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6921   -0.4753   -2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8394    0.8568   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7219    1.4545   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    1.4264    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.9554    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5272   -1.0937    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467    1.2880   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    0.0109   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    2.0366    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    2.4655   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.1190    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    1.0792    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -1.0861   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.2573    0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.7121   -1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162    0.3997   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -1.3222    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755   -1.7388   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191    0.8796    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.6593    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429   -1.9951    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -1.7057    1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327   -0.1397   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -1.6094   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7819   -0.3332    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.0989    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3124   -0.3387   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END


  Mrv1652303161704412D          

 30 29  0  0  1  0            999 V2000
   -5.1927    3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    6.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3349    2.7770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   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
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062290

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13,19,21H,2-6,12,14-18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-/t19-/m0/s1

> <INCHI_KEY>
RFAKHEWADWLSJX-ZIQRGBBDSA-N

> <FORMULA>
C20H34O3

> <MOLECULAR_WEIGHT>
322.489

> <EXACT_MASS>
322.250794955

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.41309683448345

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,12R,14Z)-12-hydroxyicosa-5,8,14-trienoic acid

> <ALOGPS_LOGP>
6.11

> <JCHEM_LOGP>
5.562373940666667

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.49882775653434

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.81977219500864

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2684130937782596

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
100.5069

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12R-HETrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062290
     RDKit          3D
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
   -7.6407    0.3807    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1404   -0.2988    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931   -0.8552   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2717    0.0604   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2477    0.7507   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -0.2088    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0441   -0.2961    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.6078   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3687    0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5412    2.2119   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    0.4808    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5120    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2863    0.0946   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -0.0892   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611   -0.8910    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.0338    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4867   -0.0964    1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -1.2005    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2246   -0.7198   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2518    0.1802    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2038    0.6104   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1535    1.3679   -0.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0767    0.1929   -2.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663    0.0050    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3187    0.1216    2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6776    1.4983    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8179   -1.1489    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8837    0.4202   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -1.5335   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -1.6193    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6921   -0.4753   -2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8394    0.8568   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7219    1.4545   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    1.4264    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.9554    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5272   -1.0937    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467    1.2880   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    0.0109   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    2.0366    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    2.4655   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.1190    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    1.0792    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -1.0861   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.2573    0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.7121   -1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162    0.3997   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -1.3222    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755   -1.7388   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191    0.8796    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.6593    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429   -1.9951    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -1.7057    1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327   -0.1397   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -1.6094   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7819   -0.3332    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.0989    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3124   -0.3387   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0      -9.693   6.724   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -8.359   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.026   6.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.026   8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.692   9.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.692  10.574   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.358  11.344   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.026  11.344   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -8.359   4.414   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -9.693   3.644   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -7.026   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -8.359   1.334   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -5.692  -0.206   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.358   3.644   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -4.358   5.184   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0      -3.025   5.954   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -3.025   1.334   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      -0.357  -0.206   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0062290
HETATM    1  C1  UNL     1      -7.641   0.381   1.649  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.140  -0.299   0.424  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.193  -0.855  -0.554  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.272   0.060  -1.236  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.248   0.751  -0.382  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.342  -0.209   0.268  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.044  -0.296   0.160  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.264   0.608  -0.677  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.270   1.369   0.164  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.541   2.212  -0.662  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.444   0.481   1.007  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.353  -0.512   0.211  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.286   0.095  -0.753  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.580  -0.089  -0.671  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.261  -0.891   0.350  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.196   0.034   1.064  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.487  -0.096   1.140  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.208  -1.200   0.515  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.225  -0.720  -0.515  1.00  0.00           C  
HETATM   20  C19 UNL     1       8.252   0.180   0.118  1.00  0.00           C  
HETATM   21  C20 UNL     1       9.204   0.610  -0.926  1.00  0.00           C  
HETATM   22  O2  UNL     1      10.154   1.368  -0.641  1.00  0.00           O  
HETATM   23  O3  UNL     1       9.077   0.193  -2.242  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.666   0.005   1.943  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.319   0.122   2.529  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.678   1.498   1.588  1.00  0.00           H  
HETATM   27  H4  UNL     1      -8.818  -1.149   0.750  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.884   0.420  -0.081  1.00  0.00           H  
HETATM   29  H6  UNL     1      -7.717  -1.533  -1.299  1.00  0.00           H  
HETATM   30  H7  UNL     1      -6.564  -1.619   0.021  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.692  -0.475  -2.034  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.839   0.857  -1.806  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.722   1.454  -1.081  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.771   1.426   0.322  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.825  -0.955   0.922  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.527  -1.094   0.729  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.847   1.288  -1.333  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.657   0.011  -1.426  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.839   2.037   0.897  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.112   2.466  -1.426  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.069  -0.119   1.724  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.285   1.079   1.625  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.434  -1.086  -0.396  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.828  -1.257   0.878  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.861   0.712  -1.575  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.216   0.400  -1.434  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.616  -1.322   1.106  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.776  -1.739  -0.152  1.00  0.00           H  
HETATM   49  H26 UNL     1       3.719   0.880   1.552  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.055   0.659   1.699  1.00  0.00           H  
HETATM   51  H28 UNL     1       5.643  -1.995   0.053  1.00  0.00           H  
HETATM   52  H29 UNL     1       6.848  -1.706   1.306  1.00  0.00           H  
HETATM   53  H30 UNL     1       6.733  -0.140  -1.321  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.704  -1.609  -0.937  1.00  0.00           H  
HETATM   55  H32 UNL     1       8.782  -0.333   0.952  1.00  0.00           H  
HETATM   56  H33 UNL     1       7.720   1.099   0.489  1.00  0.00           H  
HETATM   57  H34 UNL     1       8.312  -0.339  -2.597  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   14   45
CONECT   14   15   46
CONECT   15   16   47   48
CONECT   16   17   17   49
CONECT   17   18   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   22   23
CONECT   23   57
END

HMDB0062290
     RDKit          3D
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid
 57 56  0  0  0  0  0  0  0  0999 V2000
   -7.6407    0.3807    1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1404   -0.2988    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931   -0.8552   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2717    0.0604   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2477    0.7507   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -0.2088    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0441   -0.2961    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.6078   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3687    0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5412    2.2119   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    0.4808    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5120    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2863    0.0946   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -0.0892   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611   -0.8910    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.0338    1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4867   -0.0964    1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -1.2005    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2246   -0.7198   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2518    0.1802    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2038    0.6104   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1535    1.3679   -0.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0767    0.1929   -2.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663    0.0050    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3187    0.1216    2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6776    1.4983    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8179   -1.1489    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8837    0.4202   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -1.5335   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -1.6193    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6921   -0.4753   -2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8394    0.8568   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7219    1.4545   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710    1.4264    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.9554    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5272   -1.0937    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467    1.2880   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    0.0109   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    2.0366    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    2.4655   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.1190    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    1.0792    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -1.0861   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.2573    0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.7121   -1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162    0.3997   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -1.3222    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755   -1.7388   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191    0.8796    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.6593    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429   -1.9951    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -1.7057    1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327   -0.1397   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -1.6094   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7819   -0.3332    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7202    1.0989    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3124   -0.3387   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  1
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-Hydroxy-5,8,14-eicosatrienoic acid	MeSH
12-Hydroxy-5,8,14-eicosatrienoic acid, (S-(Z,Z,Z))-isomer	MeSH
12-Hydroxy-5,8,14-eicosatrienoic acid, (Z,Z,Z)-isomer	MeSH
12R-Hydroxy-5Z,8Z,12Z-eicosatrienoate	Generator
12(R)DH-HETE	HMDB

Chemical Formula

C₂₀H₃₄O₃

Average Molecular Weight

322.489

Monoisotopic Molecular Weight

322.250794955

IUPAC Name

(5Z,8Z,12R,14Z)-12-hydroxyicosa-5,8,14-trienoic acid

Traditional Name

12R-HETrE

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC

InChI Identifier

InChI=1S/C20H34O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13,19,21H,2-6,12,14-18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-/t19-/m0/s1

InChI Key

RFAKHEWADWLSJX-ZIQRGBBDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
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

Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050012 )

Ontology

Not Available

Not Available

Not Available

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	0.0011 g/l	ALOGPS
LogP	6.11	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.11	ALOGPS
logP	5.56	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.3	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	15	ChemAxon
Refractivity	100.51 m³·mol⁻¹	ChemAxon
Polarizability	39.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	188.285	31661259
DarkChem	[M-H]-	188.824	31661259
DeepCCS	[M+H]+	192.323	30932474
DeepCCS	[M-H]-	190.26	30932474
DeepCCS	[M-2H]-	223.499	30932474
DeepCCS	[M+Na]+	198.236	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.7	32859911
AllCCS	[M+NH4]+	191.1	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	187.1	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	191.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid	[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	4056.3	Standard polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid	[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	2446.9	Standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid	[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])CC[C@@]([H])(O)C\C([H])=C(\[H])CCCCC	2625.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TMS,isomer #1	CCCCC/C=C\C[C@H](O)CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2551.9	Semi standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TMS,isomer #2	CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2629.3	Semi standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,2TMS,isomer #1	CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2589.1	Semi standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C[C@H](O)CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2802.6	Semi standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2885.0	Semi standard non polar	33892256
12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3094.4	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 - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r7-8972000000-fe07cc3c317f890829a8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0209-9243200000-b09e11f574f4ad0f6509	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic 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 - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Positive-QTOF	splash10-0a4i-0049000000-61e9a2d385df4e008716	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Positive-QTOF	splash10-0a4i-5894000000-aa2e090c39cd912a725a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Positive-QTOF	splash10-059f-9730000000-64abc201b67c6a940078	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Negative-QTOF	splash10-00di-0019000000-872177841a61153a7214	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Negative-QTOF	splash10-0uk9-1249000000-cbee8665c1ba104ab63b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Negative-QTOF	splash10-0a4l-9820000000-4714bd7856935e2c1007	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Positive-QTOF	splash10-0ab9-2329000000-4435dd80c7748c1716cb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Positive-QTOF	splash10-052u-6942000000-a013aabce47a0bcf337c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Positive-QTOF	splash10-00l6-9300000000-dda8a60055a787f4a7b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 10V, Negative-QTOF	splash10-00di-0009000000-ddad7bbed5e6056bf9d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 20V, Negative-QTOF	splash10-0uk9-0239000000-16f5e2aed445bc7c6028	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9541000000-4c9b81cc674737f6ba75	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283149

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid (HMDB0062290)

MOL for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

3D MOL for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

3D SDF for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

3D-SDF for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

PDB for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

3D PDB for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

SMILES for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

INCHI for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

Structure for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

3D Structure for HMDB0062290 (12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra