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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 00:14:06 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004679

Secondary Accession Numbers

HMDB0005080
HMDB04679
HMDB05080

Metabolite Identification

Common Name

8-HETE

Description

8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593 , 9113987 ).

Structure

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

HMDB0004679
     RDKit          3D
8-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    9.2537   -0.6257    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8266   -0.1374    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -1.3071   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.0916   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483   -0.6951    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333    0.5451    0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7944    1.5344    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    1.7116   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039    0.7146   -1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.0360   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.2049   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321   -0.4930   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049   -0.2762    0.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7067    0.6953    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    0.2061   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4530    0.4359    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147   -0.1516    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9700   -1.1727   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1814   -0.7434   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3811   -0.5626   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5397   -0.1284   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4828    0.8845   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7238   -0.8741   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.0461    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1259   -1.6557    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8130   -0.6186   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9519    0.6102   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4122    0.3127    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405   -2.1896    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7352   -1.6515   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8298   -0.3986   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187   -2.1176   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6318   -0.9749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6947   -1.5678    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840    0.6833    1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    2.3984    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388    1.9323    0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    2.7568   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.4963   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.6986   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.8885    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1372   -1.2074   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -1.1995    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    1.6057    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -0.5126   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264    1.1468   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    1.1964    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3927    0.1106    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   -1.4126   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2488   -2.0882    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3883   -1.5393   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9958    0.2136   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6178   -1.5304    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.2559    0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0498   -1.3806   -1.6575 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  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

  Mrv0541 02231219582D          

 23 22  0  0  1  0            999 V2000
   22.5282  -18.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9557  -23.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2412  -21.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3861  -16.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6716  -15.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3861  -16.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6716  -14.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3847  -20.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6703  -21.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1006  -17.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9571  -14.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8136  -19.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5282  -19.4040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.3847  -19.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6703  -21.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0992  -19.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1006  -18.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3861  -18.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2427  -19.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3861  -19.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9571  -19.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9557  -22.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6716  -19.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  6  0  0  0
  2 22  1  0  0  0  0
  3 22  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 17  2  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 16  2  0  0  0  0
 15 22  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004679

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1

> <INCHI_KEY>
NLUNAYAEIJYXRB-VYOQERLCSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.70934241111525

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720826396228208

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6769007320864375

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087107941991405

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.4695

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8(S)-hete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004679
     RDKit          3D
8-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    9.2537   -0.6257    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8266   -0.1374    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -1.3071   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.0916   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483   -0.6951    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333    0.5451    0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7944    1.5344    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    1.7116   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039    0.7146   -1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.0360   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.2049   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321   -0.4930   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049   -0.2762    0.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7067    0.6953    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    0.2061   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4530    0.4359    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147   -0.1516    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9700   -1.1727   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1814   -0.7434   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3811   -0.5626   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5397   -0.1284   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4828    0.8845   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7238   -0.8741   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.0461    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1259   -1.6557    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8130   -0.6186   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9519    0.6102   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4122    0.3127    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405   -2.1896    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7352   -1.6515   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8298   -0.3986   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187   -2.1176   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6318   -0.9749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6947   -1.5678    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840    0.6833    1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    2.3984    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388    1.9323    0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    2.7568   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.4963   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.6986   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.8885    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1372   -1.2074   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -1.1995    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    1.6057    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -0.5126   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264    1.1468   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    1.1964    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3927    0.1106    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   -1.4126   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2488   -2.0882    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3883   -1.5393   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9958    0.2136   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6178   -1.5304    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.2559    0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0498   -1.3806   -1.6575 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  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  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      42.053 -34.681   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.384 -43.151   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.050 -40.841   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      47.387 -30.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.054 -29.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.387 -31.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.054 -27.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.051 -38.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.718 -39.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      48.721 -32.371   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      44.720 -26.981   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.719 -36.991   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.053 -36.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.051 -36.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.718 -40.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.385 -36.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      48.721 -33.911   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      47.387 -34.681   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      43.386 -36.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      47.387 -36.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.720 -36.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      35.384 -41.611   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.054 -36.991   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8    9   14                                                       
CONECT    9    8   15                                                       
CONECT   10    6   17                                                       
CONECT   11    7                                                            
CONECT   12   13   16                                                       
CONECT   13    1   12   19                                                  
CONECT   14    8   16                                                       
CONECT   15    9   22                                                       
CONECT   16   12   14                                                       
CONECT   17   10   18                                                       
CONECT   18   17   20                                                       
CONECT   19   13   21                                                       
CONECT   20   18   23                                                       
CONECT   21   19   23                                                       
CONECT   22    2    3   15                                                  
CONECT   23   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0004679
HETATM    1  C1  UNL     1       9.254  -0.626   0.714  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.827  -0.137   0.357  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.122  -1.307  -0.198  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.745  -1.092  -0.662  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.648  -0.695   0.226  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.633   0.545   0.953  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.794   1.534   0.817  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.658   1.712  -0.067  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.304   0.715  -1.046  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.178   0.036  -1.118  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.103   0.205  -0.183  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.032  -0.493  -0.274  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.105  -0.276   0.722  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.707   0.695   1.673  1.00  0.00           O  
HETATM   15  C14 UNL     1      -3.351   0.206  -0.012  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.453   0.436   0.911  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.615  -0.152   0.897  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.970  -1.173  -0.109  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.181  -0.743  -0.927  1.00  0.00           C  
HETATM   20  C19 UNL     1      -8.381  -0.563  -0.009  1.00  0.00           C  
HETATM   21  C20 UNL     1      -9.540  -0.128  -0.845  1.00  0.00           C  
HETATM   22  O2  UNL     1      -9.483   0.884  -1.567  1.00  0.00           O  
HETATM   23  O3  UNL     1     -10.724  -0.874  -0.825  1.00  0.00           O  
HETATM   24  H1  UNL     1       9.709   0.046   1.472  1.00  0.00           H  
HETATM   25  H2  UNL     1       9.126  -1.656   1.098  1.00  0.00           H  
HETATM   26  H3  UNL     1       9.813  -0.619  -0.233  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.952   0.610  -0.467  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.412   0.313   1.247  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.140  -2.190   0.539  1.00  0.00           H  
HETATM   30  H7  UNL     1       7.735  -1.651  -1.100  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.830  -0.399  -1.569  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.419  -2.118  -1.098  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.632  -0.975  -0.176  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.695  -1.568   1.054  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.384   0.683   1.751  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.004   2.398   1.519  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.739   1.932   0.568  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.745   2.757  -0.593  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.041   0.496  -1.843  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.060  -0.699  -1.937  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.156   0.889   0.627  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.137  -1.207  -1.081  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.292  -1.199   1.302  1.00  0.00           H  
HETATM   44  H21 UNL     1      -1.953   1.606   1.349  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.554  -0.513  -0.793  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.026   1.147  -0.534  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.286   1.196   1.715  1.00  0.00           H  
HETATM   48  H25 UNL     1      -6.393   0.111   1.671  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.180  -1.413  -0.812  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.249  -2.088   0.478  1.00  0.00           H  
HETATM   51  H28 UNL     1      -7.388  -1.539  -1.659  1.00  0.00           H  
HETATM   52  H29 UNL     1      -6.996   0.214  -1.448  1.00  0.00           H  
HETATM   53  H30 UNL     1      -8.618  -1.530   0.463  1.00  0.00           H  
HETATM   54  H31 UNL     1      -8.194   0.256   0.723  1.00  0.00           H  
HETATM   55  H32 UNL     1     -11.050  -1.381  -1.658  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   15   43
CONECT   14   44
CONECT   15   16   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0004679
     RDKit          3D
8-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    9.2537   -0.6257    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8266   -0.1374    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -1.3071   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.0916   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483   -0.6951    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333    0.5451    0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7944    1.5344    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    1.7116   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039    0.7146   -1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.0360   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.2049   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321   -0.4930   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049   -0.2762    0.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7067    0.6953    1.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    0.2061   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4530    0.4359    0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147   -0.1516    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9700   -1.1727   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1814   -0.7434   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3811   -0.5626   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5397   -0.1284   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4828    0.8845   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7238   -0.8741   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.0461    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1259   -1.6557    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8130   -0.6186   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9519    0.6102   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4122    0.3127    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405   -2.1896    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7352   -1.6515   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8298   -0.3986   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187   -2.1176   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6318   -0.9749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6947   -1.5678    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840    0.6833    1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    2.3984    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388    1.9323    0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    2.7568   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.4963   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.6986   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.8885    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1372   -1.2074   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -1.1995    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    1.6057    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535   -0.5126   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264    1.1468   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    1.1964    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3927    0.1106    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804   -1.4126   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2488   -2.0882    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3883   -1.5393   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9958    0.2136   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6178   -1.5304    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.2559    0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0498   -1.3806   -1.6575 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  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid	ChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid	ChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoic acid	ChEBI
(8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoic acid	ChEBI
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid	ChEBI
8(S)-Hydroxyeicosatetraenoic acid	ChEBI
8S-HETE	ChEBI
(5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoate	Generator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoate	Generator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoate	Generator
(8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoate	Generator
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoate	Generator
8(S)-Hydroxyeicosatetraenoate	Generator
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer	HMDB
8-Hydroxyeicosatetraenoic acid	HMDB
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-isomer	HMDB
(5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoate	HMDB
(5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoic acid	HMDB
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate	HMDB
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acid	HMDB
8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoate	HMDB
8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid

Traditional Name

8(S)-hete

CAS Registry Number

98462-03-4

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1

InChI Key

NLUNAYAEIJYXRB-VYOQERLCSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic 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

HETE (CHEBI:34486 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14776 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060006 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004679)

Cellular substructure

Extracellular (HMDB: HMDB0004679)
Membrane (HMDB: HMDB0004679)

Source

Exogenous

Exogenous (HMDB: HMDB0004679)

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: HMDB0004679)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	185.067	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001864

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.87	ALOGPS
logP	5.36	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	37.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.443	31661259
DarkChem	[M-H]-	188.356	31661259
DeepCCS	[M+H]+	194.33	30932474
DeepCCS	[M-H]-	191.972	30932474
DeepCCS	[M-2H]-	224.858	30932474
DeepCCS	[M+Na]+	200.423	30932474
AllCCS	[M+H]+	187.0	32859911
AllCCS	[M+H-H2O]+	184.1	32859911
AllCCS	[M+NH4]+	189.7	32859911
AllCCS	[M+Na]+	190.4	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	187.3	32859911
AllCCS	[M+HCOO]-	189.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-HETE	CCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O	4156.8	Standard polar	33892256
8-HETE	CCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O	2419.9	Standard non polar	33892256
8-HETE	CCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O	2593.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-HETE,1TMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O[Si](C)(C)C	2735.1	Semi standard non polar	33892256
8-HETE,1TMS,isomer #2	CCCCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCC(=O)O[Si](C)(C)C	2630.7	Semi standard non polar	33892256
8-HETE,2TMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2705.9	Semi standard non polar	33892256
8-HETE,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2981.6	Semi standard non polar	33892256
8-HETE,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2872.6	Semi standard non polar	33892256
8-HETE,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3192.1	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-HETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gvp-9873000000-8211b99c90a885b091c9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-HETE GC-MS (2 TMS) - 70eV, Positive	splash10-004j-9124200000-30e0b0a2d30ec66fb8f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-HETE GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-HETE 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-HETE 10V, Positive-QTOF	splash10-0udi-0149000000-1b14f944e91c989f99f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 20V, Positive-QTOF	splash10-0zia-5984000000-8f3d10aef9fa823312e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 40V, Positive-QTOF	splash10-014l-9530000000-05fe7e1e9e477bb82828	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 10V, Negative-QTOF	splash10-014i-0019000000-5d3b737e28bd5ef8e694	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 20V, Negative-QTOF	splash10-0uxr-1249000000-8e5d74e8305ef73a6b16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 40V, Negative-QTOF	splash10-0a4l-9630000000-949f0536427c39b9dddf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 10V, Negative-QTOF	splash10-014i-0009000000-26408992e4d02820d7db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 20V, Negative-QTOF	splash10-0gb9-1349000000-c600b24f75f55f01a374	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 40V, Negative-QTOF	splash10-0ac3-9761000000-bbaf759d3a09618e7f95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 10V, Positive-QTOF	splash10-0udi-1449000000-77497dbdc78a478cb017	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 20V, Positive-QTOF	splash10-0fl9-5922000000-9b495b5a9ffb5dbf5128	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-HETE 40V, Positive-QTOF	splash10-052f-9200000000-d2a456a18db9ecb16576	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	0.000749 +/- 0.000033 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.00209 +/- 0.00016 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000512 +/- 0.000367 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.000536 +/- 0.0004 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000055 +/- 0.000034 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

FDB023400

KNApSAcK ID

Not Available

Chemspider ID

4446278

KEGG Compound ID

C14776

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vâlcele, Covasna

METLIN ID

Not Available

PubChem Compound

5283154

PDB ID

Not Available

ChEBI ID

34486

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

Yu K, Bayona W, Kallen CB, Harding HP, Ravera CP, McMahon G, Brown M, Lazar MA: Differential activation of peroxisome proliferator-activated receptors by eicosanoids. J Biol Chem. 1995 Oct 13;270(41):23975-83. [PubMed:7592593 ]
Kliewer SA, Sundseth SS, Jones SA, Brown PJ, Wisely GB, Koble CS, Devchand P, Wahli W, Willson TM, Lenhard JM, Lehmann JM: Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors alpha and gamma. Proc Natl Acad Sci U S A. 1997 Apr 29;94(9):4318-23. [PubMed:9113987 ]

Showing metabocard for 8-HETE (HMDB0004679)

MOL for HMDB0004679 (8-HETE)

3D MOL for HMDB0004679 (8-HETE)

3D SDF for HMDB0004679 (8-HETE)

3D-SDF for HMDB0004679 (8-HETE)

PDB for HMDB0004679 (8-HETE)

3D PDB for HMDB0004679 (8-HETE)

SMILES for HMDB0004679 (8-HETE)

INCHI for HMDB0004679 (8-HETE)

Structure for HMDB0004679 (8-HETE)

3D Structure for HMDB0004679 (8-HETE)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra