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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 02:10:37 UTC

Update Date

2022-03-07 03:17:55 UTC

HMDB ID

HMDB0062486

Secondary Accession Numbers

HMDB62486

Metabolite Identification

Common Name

5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid

Description

(6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds (6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv1652303231703102D          

 34 33  0  0  0  0            999 V2000
   -0.3829    8.8539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    9.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   10.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   10.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    9.2664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    8.0289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.9039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END

HMDB0062486
     RDKit          3D
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    9.1406    1.6324   -0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0526    0.3044   -1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150   -0.6391   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4666   -0.2909    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5277   -1.2377    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -0.6995    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796   -1.3209    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539   -0.8700    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412    0.3871    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    1.4773    0.4977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    0.7499    1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223    0.0465    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    0.4030    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.3428   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519   -0.0338   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -0.7496   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581   -0.5522   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    0.3223   -2.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370   -0.0043    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9388    0.1285   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5908    0.6549    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0432    0.8136    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5133    1.4796    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9094    0.2209    1.8571 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336    2.1248   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5227    1.4566    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8457    2.2547   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8168    0.4668   -2.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0720   -0.1639   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0056   -1.6127   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6050    0.6811    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -2.2022    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429   -1.4672    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815    0.2073    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3881   -2.2378   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.6685    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386   -0.7182   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275    0.2249    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    2.2908    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184    1.5920    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.8226   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083    1.2617    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700   -1.1843   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421    0.8051    0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -1.5947   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805   -1.5068   -1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1984    0.5063   -2.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0577    1.0261    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3420   -0.6467    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2873   -0.9422   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501    0.7261   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.0562    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0920    1.6015    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9136   -0.8139    1.8159 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  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END


  Mrv1652303231703102D          

 34 33  0  0  0  0            999 V2000
   -0.3829    8.8539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    9.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   10.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   10.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    9.2664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    8.0289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.9039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062486

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6+,14-10+,15-11+

> <INCHI_KEY>
BISQPGCQOHLHQK-RUEGXZCXSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.524941871056505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
3.7636270203333324

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720813880416213

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725912485

> <JCHEM_PKA_STRONGEST_BASIC>
-1.274938646611163

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
104.1016

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,12-DiHEPE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062486
     RDKit          3D
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    9.1406    1.6324   -0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0526    0.3044   -1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150   -0.6391   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4666   -0.2909    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5277   -1.2377    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -0.6995    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796   -1.3209    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539   -0.8700    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412    0.3871    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    1.4773    0.4977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    0.7499    1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223    0.0465    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    0.4030    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.3428   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519   -0.0338   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -0.7496   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581   -0.5522   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    0.3223   -2.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370   -0.0043    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9388    0.1285   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5908    0.6549    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0432    0.8136    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5133    1.4796    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9094    0.2209    1.8571 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336    2.1248   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5227    1.4566    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8457    2.2547   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8168    0.4668   -2.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0720   -0.1639   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0056   -1.6127   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6050    0.6811    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -2.2022    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429   -1.4672    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815    0.2073    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3881   -2.2378   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.6685    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386   -0.7182   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275    0.2249    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    2.2908    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184    1.5920    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.8226   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083    1.2617    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700   -1.1843   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421    0.8051    0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -1.5947   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805   -1.5068   -1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1984    0.5063   -2.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0577    1.0261    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3420   -0.6467    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2873   -0.9422   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501    0.7261   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.0562    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0920    1.6015    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9136   -0.8139    1.8159 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  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0      -0.715  16.527   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -2.048  17.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.048  18.837   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.715  19.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.382  16.527   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      -4.716  17.297   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0      -3.382  14.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.048  14.217   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -0.715  14.987   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -2.048  12.677   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -3.382  11.907   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      -0.715  11.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.715  10.367   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.048   9.597   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.619   9.597   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.953  10.367   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       0.619   8.057   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -0.715   7.287   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       3.286   8.057   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.619   4.977   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.620   5.747   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.953   2.667   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0062486
HETATM    1  C1  UNL     1       9.141   1.632  -0.946  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.053   0.304  -1.655  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.115  -0.639  -1.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.467  -0.291   0.083  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.528  -1.238   0.729  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.158  -0.699   0.806  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.180  -1.321   0.217  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.754  -0.870   0.228  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.541   0.387   1.004  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.271   1.477   0.498  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.108   0.750   1.028  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.222   0.046   0.358  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.208   0.403   0.378  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.033  -0.343  -0.310  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.452  -0.034  -0.325  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.326  -0.750  -1.001  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.758  -0.552  -1.100  1.00  0.00           C  
HETATM   18  O2  UNL     1      -6.011   0.322  -2.177  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.437  -0.004   0.132  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.939   0.128  -0.152  1.00  0.00           C  
HETATM   21  C19 UNL     1      -8.591   0.655   1.112  1.00  0.00           C  
HETATM   22  C20 UNL     1     -10.043   0.814   0.953  1.00  0.00           C  
HETATM   23  O3  UNL     1     -10.513   1.480   0.005  1.00  0.00           O  
HETATM   24  O4  UNL     1     -10.909   0.221   1.857  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.134   2.125  -0.959  1.00  0.00           H  
HETATM   26  H2  UNL     1       9.523   1.457   0.077  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.846   2.255  -1.534  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.817   0.467  -2.722  1.00  0.00           H  
HETATM   29  H5  UNL     1      10.072  -0.164  -1.610  1.00  0.00           H  
HETATM   30  H6  UNL     1       8.006  -1.613  -1.485  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.605   0.681   0.525  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.553  -2.202   0.150  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.843  -1.467   1.773  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.982   0.207   1.356  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.388  -2.238  -0.334  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.139  -1.668   0.683  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.439  -0.718  -0.828  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.827   0.225   2.082  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.915   2.291   0.944  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.718   1.592   1.583  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.518  -0.823  -0.236  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.508   1.262   0.958  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.670  -1.184  -0.860  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.842   0.805   0.226  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.897  -1.595  -1.551  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.281  -1.507  -1.392  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.198   0.506  -2.695  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.058   1.026   0.258  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.342  -0.647   1.013  1.00  0.00           H  
HETATM   50  H26 UNL     1      -8.287  -0.942  -0.267  1.00  0.00           H  
HETATM   51  H27 UNL     1      -8.150   0.726  -1.044  1.00  0.00           H  
HETATM   52  H28 UNL     1      -8.399  -0.056   1.937  1.00  0.00           H  
HETATM   53  H29 UNL     1      -8.092   1.602   1.421  1.00  0.00           H  
HETATM   54  H30 UNL     1     -10.914  -0.814   1.816  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4    4   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   11   38
CONECT   10   39
CONECT   11   12   12   40
CONECT   12   13   41
CONECT   13   14   14   42
CONECT   14   15   43
CONECT   15   16   16   44
CONECT   16   17   45
CONECT   17   18   19   46
CONECT   18   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   54
END

HMDB0062486
     RDKit          3D
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    9.1406    1.6324   -0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0526    0.3044   -1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150   -0.6391   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4666   -0.2909    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5277   -1.2377    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -0.6995    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796   -1.3209    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539   -0.8700    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412    0.3871    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    1.4773    0.4977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084    0.7499    1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223    0.0465    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    0.4030    0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.3428   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519   -0.0338   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -0.7496   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581   -0.5522   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    0.3223   -2.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370   -0.0043    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9388    0.1285   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5908    0.6549    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0432    0.8136    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5133    1.4796    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9094    0.2209    1.8571 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336    2.1248   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5227    1.4566    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8457    2.2547   -1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8168    0.4668   -2.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0720   -0.1639   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0056   -1.6127   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6050    0.6811    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -2.2022    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429   -1.4672    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815    0.2073    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3881   -2.2378   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.6685    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386   -0.7182   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275    0.2249    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    2.2908    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184    1.5920    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.8226   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083    1.2617    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700   -1.1843   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421    0.8051    0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -1.5947   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805   -1.5068   -1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1984    0.5063   -2.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0577    1.0261    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3420   -0.6467    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2873   -0.9422   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501    0.7261   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3988   -0.0562    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0920    1.6015    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9136   -0.8139    1.8159 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  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6E,8E,10E,14E,17E)-5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoate	Generator
5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoate	Generator
Leukotriene b5	HMDB
LTB 5	HMDB

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.456

Monoisotopic Molecular Weight

334.214409446

IUPAC Name

(6E,8E,10E,14E,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid

Traditional Name

5,12-DiHEPE

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6+,14-10+,15-11+

InChI Key

BISQPGCQOHLHQK-RUEGXZCXSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroxyeicosapentaenoic 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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062486)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.016 g/l	ALOGPS
LogP	4.68	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.68	ALOGPS
logP	3.76	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	104.1 m³·mol⁻¹	ChemAxon
Polarizability	40.52 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]+	192.37	31661259
DarkChem	[M-H]-	189.593	31661259
DeepCCS	[M+H]+	210.263	30932474
DeepCCS	[M-H]-	208.438	30932474
DeepCCS	[M-2H]-	241.679	30932474
DeepCCS	[M+Na]+	215.869	30932474
AllCCS	[M+H]+	189.6	32859911
AllCCS	[M+H-H2O]+	186.7	32859911
AllCCS	[M+NH4]+	192.3	32859911
AllCCS	[M+Na]+	193.0	32859911
AllCCS	[M-H]-	186.0	32859911
AllCCS	[M+Na-2H]-	187.8	32859911
AllCCS	[M+HCOO]-	189.9	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	5.03 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6995 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2883.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	295.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	214.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	726.9 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	464.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1601.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	592.6 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	1447.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	334.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	305.5 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
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid	[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O	4609.8	Standard polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid	[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O	2386.3	Standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid	[H]\C(CC)=C(\[H])C\C([H])=C(/[H])CC(O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(O)CCCC(O)=O	2735.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C	2990.2	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #2	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C	2996.0	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TMS,isomer #3	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C	2878.9	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3022.2	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #2	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2925.7	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TMS,isomer #3	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2932.0	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2919.5	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3236.8	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #2	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3235.7	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,1TBDMS,isomer #3	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3112.2	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3467.2	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #2	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3392.4	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,2TBDMS,isomer #3	CC/C=C/C/C=C/CC(O)/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3401.3	Semi standard non polar	33892256
5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid,3TBDMS,isomer #1	CC/C=C/C/C=C/CC(/C=C/C=C/C=C/C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3660.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-5976000000-1308051082500b532d7b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-002u-9114550000-fb98f8ad419bf0e2f1eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic 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 - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOF	splash10-014j-0089000000-945a81862277ca8ffccd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOF	splash10-00kk-3492000000-1307f5bf34685a04ff67	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOF	splash10-0a4u-9550000000-dd3a21bd0ec9a9c3281b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOF	splash10-00lr-0029000000-aea24fc310a30c0083f4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOF	splash10-0159-2359000000-2767c62677c595b5c621	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOF	splash10-0a4l-9440000000-c5ad6a89519cdea928ca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Negative-QTOF	splash10-0159-0019000000-ebe312919323a70b435d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Negative-QTOF	splash10-00lr-3449000000-33dea2da13cb74cad0bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Negative-QTOF	splash10-059l-5391000000-da0f2fad428f71a9a01d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 10V, Positive-QTOF	splash10-00kb-0196000000-fb8a4628f13adee8bffa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 20V, Positive-QTOF	splash10-0002-1391000000-01dd8cbef267af45ff7a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid 40V, Positive-QTOF	splash10-0ar0-9610000000-b9ceb4ac3bd3c9071f0a	2021-09-25	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

5312988

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 5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid (HMDB0062486)

MOL for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

3D MOL for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

3D SDF for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

3D-SDF for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

PDB for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

3D PDB for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

SMILES for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

INCHI for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

Structure for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

3D Structure for HMDB0062486 (5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra