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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:47 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002311

Secondary Accession Numbers

HMDB0002351
HMDB0004676
HMDB02311
HMDB02351
HMDB04676

Metabolite Identification

Common Name

8,9-DiHETrE

Description

8,9-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid (AA) metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. P450converts AA to 8,9- dihydroxyeicosatrienoic acid. This enzymatic pathway was first described in liver; however, it is now clear that AA can be metabolized by P450 in many tissues including the pituitary gland, eye, kidney, adrenal gland, and blood vessels. (PMID: 17431031 , 11700990 ).

Structure

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

HMDB0002311
     RDKit          3D
8,9-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.2286   -2.1194   -1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1156   -0.9059   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6477    0.2617   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438    0.8748   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.4543   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9598    0.5221    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697    0.2885    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958    0.9487    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.1358    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5213   -0.4116    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.3354    2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.9565    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    1.8191    1.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912   -0.0457    2.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922   -0.8120    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    0.5546    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    1.6121    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    1.5602    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9493    0.4122    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7520   -0.1145   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810   -1.2890   -1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.8390   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3414   -3.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3189   -2.9490   -3.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2975   -2.6193   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6582   -2.8476   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985   -1.9249   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0666   -1.2837   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5149   -0.7561   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    0.0802   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4294    1.0846   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2233    1.6787   -2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831    0.1735   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1304    2.1156   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    2.2162   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8685   -0.0253    0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8631   -0.4368    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.5046    1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539    1.6164    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -0.7730   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.2659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042    1.1812    2.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -0.3460    3.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.6405    3.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    1.3820    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -0.8063    2.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -1.7142    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401   -0.2165    2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0854    3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    2.5366    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424    2.4241   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0219    0.7346    0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.4206    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7074   -0.4185   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683    0.6995   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -2.0154   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7447   -1.0047   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3171   -2.9158   -2.9074 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

  Mrv0541 02231219292D          

 24 23  0  0  0  0            999 V2000
   25.8847  -12.5226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1701  -14.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4571  -17.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1716  -15.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8847  -13.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1701  -13.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5991  -13.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4557  -13.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0267  -10.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7412   -9.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3136  -13.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7412  -13.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0267  -10.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0281  -14.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7412   -8.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0281  -13.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7426  -14.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0267  -13.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0267  -12.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3122  -11.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3122  -12.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7426  -15.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4557   -8.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4571  -16.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 18  2  0  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 23  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002311

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-

> <INCHI_KEY>
DCJBINATHQHPKO-TYAUOURKSA-N

> <FORMULA>
C20H34O4

> <MOLECULAR_WEIGHT>
338.4816

> <EXACT_MASS>
338.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.17499353943075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,11Z,14Z)-8,9-dihydroxyicosa-5,11,14-trienoic acid

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
4.487470333666667

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.840474909710785

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.363630032162088

> <JCHEM_PKA_STRONGEST_BASIC>
-3.174302440732254

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
101.86840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,9-DiHETrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002311
     RDKit          3D
8,9-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.2286   -2.1194   -1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1156   -0.9059   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6477    0.2617   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438    0.8748   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.4543   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9598    0.5221    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697    0.2885    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958    0.9487    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.1358    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5213   -0.4116    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.3354    2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.9565    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    1.8191    1.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912   -0.0457    2.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922   -0.8120    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    0.5546    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    1.6121    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    1.5602    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9493    0.4122    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7520   -0.1145   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810   -1.2890   -1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.8390   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3414   -3.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3189   -2.9490   -3.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2975   -2.6193   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6582   -2.8476   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985   -1.9249   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0666   -1.2837   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5149   -0.7561   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    0.0802   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4294    1.0846   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2233    1.6787   -2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831    0.1735   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1304    2.1156   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    2.2162   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8685   -0.0253    0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8631   -0.4368    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.5046    1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539    1.6164    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -0.7730   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.2659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042    1.1812    2.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -0.3460    3.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.6405    3.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    1.3820    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -0.8063    2.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -1.7142    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401   -0.2165    2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0854    3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    2.5366    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424    2.4241   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0219    0.7346    0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.4206    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7074   -0.4185   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683    0.6995   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -2.0154   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7447   -1.0047   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3171   -2.9158   -2.9074 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.318 -23.376   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      46.984 -27.226   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      54.987 -31.846   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      56.320 -29.536   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      48.318 -24.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.984 -25.686   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.652 -25.686   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.651 -24.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.983 -18.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.317 -17.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.985 -24.916   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.317 -25.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.983 -20.295   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      52.319 -27.226   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.317 -16.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.319 -25.686   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      53.653 -27.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.983 -24.916   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.983 -23.376   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.649 -21.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.649 -22.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      53.653 -29.536   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.651 -15.675   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      54.987 -30.306   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    6    7                                                  
CONECT    6    2    5    8                                                  
CONECT    7    5   11                                                       
CONECT    8    6   12                                                       
CONECT    9   10   13                                                       
CONECT   10    9   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   18                                                       
CONECT   13    9   20                                                       
CONECT   14   16   17                                                       
CONECT   15   10   23                                                       
CONECT   16   11   14                                                       
CONECT   17   14   22                                                       
CONECT   18   12   19                                                       
CONECT   19   18   21                                                       
CONECT   20   13   21                                                       
CONECT   21   19   20                                                       
CONECT   22   17   24                                                       
CONECT   23   15                                                            
CONECT   24    3    4   22                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002311
HETATM    1  C1  UNL     1      -6.229  -2.119  -1.285  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.116  -0.906  -1.240  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.648   0.262  -1.999  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.344   0.875  -1.756  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.005   1.454  -0.422  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.960   0.522   0.670  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.870   0.289   1.365  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.596   0.949   1.100  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.617  -0.136   0.786  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.521  -0.412   1.416  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.064   0.335   2.582  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.306   0.957   2.277  1.00  0.00           C  
HETATM   13  O1  UNL     1       1.264   1.819   1.192  1.00  0.00           O  
HETATM   14  C13 UNL     1       2.391  -0.046   2.091  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.292  -0.812   0.936  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.798   0.555   2.230  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.077   1.612   1.261  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.030   1.560   0.378  1.00  0.00           C  
HETATM   19  C17 UNL     1       5.949   0.412   0.251  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.752  -0.114  -1.180  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.681  -1.289  -1.335  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.541  -1.839  -2.683  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.752  -1.341  -3.496  1.00  0.00           O  
HETATM   24  O4  UNL     1       7.319  -2.949  -3.053  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.297  -2.619  -2.261  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.658  -2.848  -0.536  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.198  -1.925  -0.942  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.067  -1.284  -1.814  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.515  -0.756  -0.238  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.821   0.080  -3.121  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.429   1.085  -1.813  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.223   1.679  -2.572  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.483   0.173  -2.073  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.130   2.116  -0.587  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.864   2.216  -0.191  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.869  -0.025   0.978  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.863  -0.437   2.205  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.262   1.505   1.990  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.554   1.616   0.216  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.874  -0.773  -0.098  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.063  -1.266   1.026  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.704   1.181   2.827  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.065  -0.346   3.480  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.583   1.640   3.151  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.145   1.382   0.333  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.259  -0.806   2.932  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.674  -1.714   1.084  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.540  -0.216   2.375  1.00  0.00           H  
HETATM   49  H25 UNL     1       3.745   1.085   3.243  1.00  0.00           H  
HETATM   50  H26 UNL     1       3.450   2.537   1.264  1.00  0.00           H  
HETATM   51  H27 UNL     1       5.142   2.424  -0.300  1.00  0.00           H  
HETATM   52  H28 UNL     1       7.022   0.735   0.270  1.00  0.00           H  
HETATM   53  H29 UNL     1       5.792  -0.421   0.917  1.00  0.00           H  
HETATM   54  H30 UNL     1       4.707  -0.418  -1.278  1.00  0.00           H  
HETATM   55  H31 UNL     1       5.968   0.700  -1.909  1.00  0.00           H  
HETATM   56  H32 UNL     1       6.408  -2.015  -0.534  1.00  0.00           H  
HETATM   57  H33 UNL     1       7.745  -1.005  -1.172  1.00  0.00           H  
HETATM   58  H34 UNL     1       8.317  -2.916  -2.907  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   10   40
CONECT   10   11   41
CONECT   11   12   42   43
CONECT   12   13   14   44
CONECT   13   45
CONECT   14   15   16   46
CONECT   15   47
CONECT   16   17   48   49
CONECT   17   18   18   50
CONECT   18   19   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   23   24
CONECT   24   58
END

HMDB0002311
     RDKit          3D
8,9-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.2286   -2.1194   -1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1156   -0.9059   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6477    0.2617   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3438    0.8748   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.4543   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9598    0.5221    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697    0.2885    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958    0.9487    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.1358    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5213   -0.4116    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.3354    2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.9565    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    1.8191    1.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912   -0.0457    2.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922   -0.8120    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    0.5546    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    1.6121    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    1.5602    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9493    0.4122    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7520   -0.1145   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810   -1.2890   -1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -1.8390   -2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7516   -1.3414   -3.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3189   -2.9490   -3.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2975   -2.6193   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6582   -2.8476   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985   -1.9249   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0666   -1.2837   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5149   -0.7561   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    0.0802   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4294    1.0846   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2233    1.6787   -2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831    0.1735   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1304    2.1156   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    2.2162   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8685   -0.0253    0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8631   -0.4368    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.5046    1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539    1.6164    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -0.7730   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.2659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042    1.1812    2.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -0.3460    3.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.6405    3.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    1.3820    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -0.8063    2.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -1.7142    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401   -0.2165    2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0854    3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    2.5366    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1424    2.4241   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0219    0.7346    0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.4206    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7074   -0.4185   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683    0.6995   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -2.0154   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7447   -1.0047   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3171   -2.9158   -2.9074 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoic acid	ChEBI
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoic acid	ChEBI
8,9-DHET	ChEBI
8,9-Dihydroxy-5Z,11Z,14Z-eicosatrienoic acid	ChEBI
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoic acid	ChEBI
8,9-Dihydroxyeicosatrienoic acid	ChEBI
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoate	Generator
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoate	Generator
8,9-Dihydroxy-5Z,11Z,14Z-eicosatrienoate	Generator
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoate	Generator
8,9-Dihydroxyeicosatrienoate	Generator
(+/-)8,9-dihetre	HMDB

Chemical Formula

C₂₀H₃₄O₄

Average Molecular Weight

338.4816

Monoisotopic Molecular Weight

338.245709576

IUPAC Name

(5Z,11Z,14Z)-8,9-dihydroxyicosa-5,11,14-trienoic acid

Traditional Name

8,9-DiHETrE

CAS Registry Number

192461-96-4

SMILES

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

InChI Identifier

InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-

InChI Key

DCJBINATHQHPKO-TYAUOURKSA-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
Unsaturated fatty acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

DHET (CHEBI:63970 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14773 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050006 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0002311)

Cellular substructure

Extracellular (HMDB: HMDB0002311)
Membrane (HMDB: HMDB0002311)

Source

Exogenous

Exogenous (HMDB: HMDB0002311)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002311)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	5.45	ALOGPS
logP	4.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3.2	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	15	ChemAxon
Refractivity	101.87 m³·mol⁻¹	ChemAxon
Polarizability	39.17 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]+	191.208	31661259
DarkChem	[M-H]-	189.249	31661259
DeepCCS	[M+H]+	193.231	30932474
DeepCCS	[M-H]-	190.873	30932474
DeepCCS	[M-2H]-	223.759	30932474
DeepCCS	[M+Na]+	199.324	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.9	32859911
AllCCS	[M+NH4]+	195.1	32859911
AllCCS	[M+Na]+	195.8	32859911
AllCCS	[M-H]-	189.3	32859911
AllCCS	[M+Na-2H]-	191.2	32859911
AllCCS	[M+HCOO]-	193.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8,9-DiHETrE	CCCCC\C=C/C\C=C/CC(O)C(O)C\C=C/CCCC(O)=O	4178.7	Standard polar	33892256
8,9-DiHETrE	CCCCC\C=C/C\C=C/CC(O)C(O)C\C=C/CCCC(O)=O	2415.7	Standard non polar	33892256
8,9-DiHETrE	CCCCC\C=C/C\C=C/CC(O)C(O)C\C=C/CCCC(O)=O	2614.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8,9-DiHETrE,1TMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCC(=O)O	2796.2	Semi standard non polar	33892256
8,9-DiHETrE,1TMS,isomer #2	CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2795.5	Semi standard non polar	33892256
8,9-DiHETrE,1TMS,isomer #3	CCCCC/C=C\C/C=C\CC(O)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2719.5	Semi standard non polar	33892256
8,9-DiHETrE,2TMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2797.9	Semi standard non polar	33892256
8,9-DiHETrE,2TMS,isomer #2	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2739.9	Semi standard non polar	33892256
8,9-DiHETrE,2TMS,isomer #3	CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2740.9	Semi standard non polar	33892256
8,9-DiHETrE,3TMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2726.5	Semi standard non polar	33892256
8,9-DiHETrE,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCC(=O)O	3049.5	Semi standard non polar	33892256
8,9-DiHETrE,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3050.2	Semi standard non polar	33892256
8,9-DiHETrE,1TBDMS,isomer #3	CCCCC/C=C\C/C=C\CC(O)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2970.1	Semi standard non polar	33892256
8,9-DiHETrE,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3232.4	Semi standard non polar	33892256
8,9-DiHETrE,2TBDMS,isomer #2	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3211.2	Semi standard non polar	33892256
8,9-DiHETrE,2TBDMS,isomer #3	CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3213.1	Semi standard non polar	33892256
8,9-DiHETrE,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(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	3423.4	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 - 8,9-DiHETrE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kpi-3931000000-9660c7e0c24b66a14563	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-DiHETrE GC-MS (3 TMS) - 70eV, Positive	splash10-0f9i-9212430000-caddc47ca14076a600eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-DiHETrE 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 - 8,9-DiHETrE 10V, Positive-QTOF	splash10-00di-0119000000-0276473f3dd77d612b5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Positive-QTOF	splash10-0ue9-5913000000-4d67f2c146851cdb48db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Positive-QTOF	splash10-0hgx-9400000000-998c31cc7528c1659a1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Negative-QTOF	splash10-000i-0019000000-092edd96d90bb2988b32	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Negative-QTOF	splash10-0699-1925000000-106e392714fab8f93cd6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Negative-QTOF	splash10-0a4i-7910000000-487e4a96aea86a79fbf3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Positive-QTOF	splash10-0fk9-1209000000-f00de6b9bdba3d80e2a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Positive-QTOF	splash10-00ai-9502000000-387b760f173f7802c2d4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Positive-QTOF	splash10-069u-9200000000-1f79a95ef141e773e52a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Negative-QTOF	splash10-000i-0109000000-d7cf9ea53b7adcdc367d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Negative-QTOF	splash10-000i-3839000000-aff175e8d9191e9e8d4e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Negative-QTOF	splash10-052f-9620000000-2a240acda50a55485912	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00051 +/- 0.000066 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000294 +/- 0.000056 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000400 +/- 0.000151 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.000244 +/- 0.000078 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00013 +/- 0.00003 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022960

KNApSAcK ID

Not Available

Chemspider ID

4446268

KEGG Compound ID

C14773

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283144

PDB ID

Not Available

ChEBI ID

63970

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

Ng VY, Huang Y, Reddy LM, Falck JR, Lin ET, Kroetz DL: Cytochrome P450 eicosanoids are activators of peroxisome proliferator-activated receptor alpha. Drug Metab Dispos. 2007 Jul;35(7):1126-34. Epub 2007 Apr 12. [PubMed:17431031 ]
Nithipatikom K, Grall AJ, Holmes BB, Harder DR, Falck JR, Campbell WB: Liquid chromatographic-electrospray ionization-mass spectrometric analysis of cytochrome P450 metabolites of arachidonic acid. Anal Biochem. 2001 Nov 15;298(2):327-36. [PubMed:11700990 ]

Enzymes

Enzyme Details

1. Bifunctional epoxide hydrolase 2

General function:: Involved in catalytic activity
Specific function:: Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:: EPHX2
Uniprot ID:: P34913
Molecular weight:: 62615.22

Reactions

8,9-Epoxyeicosatrienoic acid + Water → 8,9-DiHETrE	details

Showing metabocard for 8,9-DiHETrE (HMDB0002311)

MOL for HMDB0002311 (8,9-DiHETrE)

3D MOL for HMDB0002311 (8,9-DiHETrE)

3D SDF for HMDB0002311 (8,9-DiHETrE)

3D-SDF for HMDB0002311 (8,9-DiHETrE)

PDB for HMDB0002311 (8,9-DiHETrE)

3D PDB for HMDB0002311 (8,9-DiHETrE)

SMILES for HMDB0002311 (8,9-DiHETrE)

INCHI for HMDB0002311 (8,9-DiHETrE)

Structure for HMDB0002311 (8,9-DiHETrE)

3D Structure for HMDB0002311 (8,9-DiHETrE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions