MiMeDB: Showing metabocard for 5-HETE (MMDBc0000638)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:40 UTC

Update Date

2024-04-30 19:33:22 UTC

Metabolite ID

MMDBc0000638

Metabolite Identification

Common Name

5-HETE

Description

5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.

Structure

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

HMDB0011134
     RDKit          3D
5-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.0391   -1.9109   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5246   -0.6625    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3737    0.1563    0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4219    0.5522   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976    1.3833    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813    0.5737    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    0.2714    1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    0.7086   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -0.5432   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.7332   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    0.1568   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1971    0.5569   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.2919   -1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1671   -0.3854   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -0.5898   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -1.2859    0.3449 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3207   -2.0290   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2424    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6676    0.8182    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9006    0.3451   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -0.3530    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6086   -0.5136    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0231   -0.8336    0.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9574   -2.0916   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2656   -1.8429   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6057   -2.7753   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2187   -0.8643    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0469    0.0335   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8437    1.0748    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.3822    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9358    1.1530   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0030   -0.3558   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997    2.2631    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.8599   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    0.2213    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636   -0.3420    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741    1.3595    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782    1.2351   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.2583   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505   -1.6651   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809    1.0544    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608   -0.4444    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.0867   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956    0.6322   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.7349    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9813   -0.2516   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6368   -1.9604    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2458   -2.9649    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -0.6966    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089    0.2794    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0493    1.4220   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821    1.5186    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3929    1.2687   -0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153   -0.2890   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8984   -1.5824   -0.4185 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 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


  Mrv1652310281915492D          

 23 22  0  0  0  0            999 V2000
 9997.486410001.0102    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.201410000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.916310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.631210000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.456810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.171710001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.886910000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.711910000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.427510001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.141210000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.968210000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.681910001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.397610000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.111210001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.826910000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.544710001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.771510000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.056610001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.341910000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.626810001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.909810000.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.626810001.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.486410001.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 23  1  6  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000638

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
KGIJOOYOSFUGPC-JGKLHWIESA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.13427837164788

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.865306513915215

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.584101629727195

> <JCHEM_PKA_STRONGEST_BASIC>
-1.545515302673174

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.46950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyeicosatetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011134
     RDKit          3D
5-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.0391   -1.9109   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5246   -0.6625    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3737    0.1563    0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4219    0.5522   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976    1.3833    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813    0.5737    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    0.2714    1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    0.7086   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -0.5432   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.7332   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    0.1568   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1971    0.5569   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.2919   -1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1671   -0.3854   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -0.5898   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -1.2859    0.3449 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3207   -2.0290   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2424    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6676    0.8182    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9006    0.3451   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -0.3530    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6086   -0.5136    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0231   -0.8336    0.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9574   -2.0916   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2656   -1.8429   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6057   -2.7753   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2187   -0.8643    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0469    0.0335   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8437    1.0748    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.3822    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9358    1.1530   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0030   -0.3558   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997    2.2631    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.8599   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    0.2213    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636   -0.3420    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741    1.3595    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782    1.2351   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.2583   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505   -1.6651   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809    1.0544    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608   -0.4444    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.0867   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956    0.6322   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.7349    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9813   -0.2516   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6368   -1.9604    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2458   -2.9649    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -0.6966    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089    0.2794    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0493    1.4220   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821    1.5186    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3929    1.2687   -0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153   -0.2890   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8984   -1.5824   -0.4185 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 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                                 28-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-OCT-19         0                                  
HETATM    1  C   UNK     0    8661.9758668.552   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3098667.784   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.6448668.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.9788667.784   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.5198667.784   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.8548668.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.1898667.784   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.7298667.784   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.0658668.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.3978667.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.9418667.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8677.2738668.552   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.6098667.784   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8679.9418668.552   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8681.2778667.784   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8682.6178668.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.6408667.784   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8659.3068668.552   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8657.9718667.784   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8656.6378668.552   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8655.2988667.784   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8656.6378670.094   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8661.9758670.094   0.000  0.00  0.00           O+0
CONECT    1    2   17   23                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0011134
HETATM    1  C1  UNL     1      -8.039  -1.911  -0.582  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.525  -0.663   0.086  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.374   0.156   0.676  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.422   0.552  -0.417  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.298   1.383   0.184  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.581   0.574   1.172  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.312   0.271   1.049  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.486   0.709  -0.088  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.959  -0.543  -0.747  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.680  -0.733  -0.820  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.370   0.157  -0.319  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.197   0.557  -1.486  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.470   0.292  -1.527  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.167  -0.385  -0.487  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.485  -0.590  -0.671  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.319  -1.286   0.345  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.321  -2.029  -0.252  1.00  0.00           O  
HETATM   18  C17 UNL     1       5.834  -0.242   1.307  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.668   0.818   0.672  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.901   0.345  -0.021  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.842  -0.353   0.858  1.00  0.00           C  
HETATM   22  O2  UNL     1       8.609  -0.514   2.064  1.00  0.00           O  
HETATM   23  O3  UNL     1      10.023  -0.834   0.272  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.957  -2.092  -0.417  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.266  -1.843  -1.667  1.00  0.00           H  
HETATM   26  H3  UNL     1      -8.606  -2.775  -0.177  1.00  0.00           H  
HETATM   27  H4  UNL     1      -9.219  -0.864   0.921  1.00  0.00           H  
HETATM   28  H5  UNL     1      -9.047   0.034  -0.617  1.00  0.00           H  
HETATM   29  H6  UNL     1      -7.844   1.075   1.083  1.00  0.00           H  
HETATM   30  H7  UNL     1      -6.895  -0.382   1.492  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.936   1.153  -1.197  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.003  -0.356  -0.905  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.800   2.263   0.739  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.704   1.860  -0.585  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.142   0.221   2.060  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.864  -0.342   1.848  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.674   1.360   0.225  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.078   1.235  -0.885  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.707  -1.258  -1.147  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.350  -1.665  -1.313  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.081   1.054   0.215  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.961  -0.444   0.430  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.686   1.087  -2.314  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.996   0.632  -2.441  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.735  -0.735   0.411  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.981  -0.252  -1.571  1.00  0.00           H  
HETATM   47  H24 UNL     1       4.637  -1.960   0.943  1.00  0.00           H  
HETATM   48  H25 UNL     1       6.246  -2.965   0.047  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.293  -0.697   2.192  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.909   0.279   1.696  1.00  0.00           H  
HETATM   51  H28 UNL     1       6.049   1.422  -0.028  1.00  0.00           H  
HETATM   52  H29 UNL     1       6.982   1.519   1.472  1.00  0.00           H  
HETATM   53  H30 UNL     1       8.393   1.269  -0.448  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.715  -0.289  -0.911  1.00  0.00           H  
HETATM   55  H32 UNL     1       9.898  -1.582  -0.419  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   41   42
CONECT   12   13   13   43
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   16   17   18   47
CONECT   17   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

HMDB0011134
     RDKit          3D
5-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.0391   -1.9109   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5246   -0.6625    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3737    0.1563    0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4219    0.5522   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976    1.3833    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813    0.5737    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    0.2714    1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    0.7086   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -0.5432   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.7332   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    0.1568   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1971    0.5569   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.2919   -1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1671   -0.3854   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -0.5898   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -1.2859    0.3449 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3207   -2.0290   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -0.2424    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6676    0.8182    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9006    0.3451   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -0.3530    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6086   -0.5136    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0231   -0.8336    0.2721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9574   -2.0916   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2656   -1.8429   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6057   -2.7753   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2187   -0.8643    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0469    0.0335   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8437    1.0748    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.3822    1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9358    1.1530   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0030   -0.3558   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997    2.2631    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.8599   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    0.2213    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636   -0.3420    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741    1.3595    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782    1.2351   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.2583   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505   -1.6651   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809    1.0544    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608   -0.4444    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    1.0867   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956    0.6322   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.7349    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9813   -0.2516   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6368   -1.9604    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2458   -2.9649    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -0.6966    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089    0.2794    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0493    1.4220   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821    1.5186    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3929    1.2687   -0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153   -0.2890   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8984   -1.5824   -0.4185 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 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
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 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

Synonyms

Value	Source
5-Hydroxyeicosatetraenoate	Kegg
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid	Kegg
5-Hydroxyeicosatetraenoic acid	Generator
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoate	Generator
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid	HMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid	HMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid	HMDB
5(S)-Hydroxyeicosatetraenoic acid	HMDB
5S-HETE	HMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate	HMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate	HMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate	HMDB
5(S)-Hydroxyeicosatetraenoate	HMDB
5(S)-HETE	HMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate	HMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoate	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid	HMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoate	HMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid	HMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoate	HMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoic acid	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomer	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer	HMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomer	HMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acid	HMDB
5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acid	HMDB
FA(20:4(5-OH,6E,8Z,11Z,14Z))	HMDB
FA(20:4(5S-OH,6E,8Z,11Z,14Z))	HMDB
5-HETE	HMDB

Molecular Formula

C₂₀H₃₂O₃

Average Mass

320.4663

Monoisotopic Mass

320.23514489

IUPAC Name

(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

Traditional Name

5-hydroxyeicosatetraenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

KGIJOOYOSFUGPC-JGKLHWIESA-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:28209 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C04805 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060002 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.88	ALOGPS
logP	5.36	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-1.5	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	38.13 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-7293000000-4000067abc9684c2e653	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-056s-9117300000-40397121b4b937950f9d	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0ldi-0079000000-52dac491931feca303a5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0pvi-0196000000-b7a43328bfcf1b860873	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-1000-0293000000-6e834102b17e5bbec6fc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-1000-0390000000-61ebc99aa5f8333b07d2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-03di-1930000000-b877c0d03861ddd2728d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0aor-9620000000-8cfab24155dae08cc2ca	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-014i-0910000000-90f71c96ff730ececc7c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-08fr-4900000000-e0a2e06154c966bbfcc8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0a4i-9000000000-a54cdd357529bdc9f5e3	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0149000000-eb17d14c7966577fd391	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-4693000000-a850cad35b2bb6dbc176	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9880000000-8e15d5e341c49c793973	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-eb6fa786699adba566be	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ldi-2179000000-3bed63121486cd2b2630	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9150000000-29ad65a68f2ec87b590f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-1549000000-24b83a60315e83b8c15b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fl9-6943000000-d54f4d6e30d221259591	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-9400000000-745ec239ed811dee9dbd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-7a32e9e109204e833b16	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-4149000000-3bac989e03f14b200555	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k96-9432000000-25aaec361eff0ecf2d57	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192429	Glutathione peroxidase 7	Enzyme	Q96SL4	Homo sapiens
MMDBp0192430	Epididymal secretory glutathione peroxidase	Enzyme	O75715	Homo sapiens
MMDBp0192445	Glutathione peroxidase 6	Enzyme	P59796	Homo sapiens
MMDBp0192448	Glutathione peroxidase 1	Enzyme	P07203	Homo sapiens
MMDBp0192449	Phospholipid hydroperoxide glutathione peroxidase, mitochondrial	Enzyme	P36969	Homo sapiens
MMDBp0192450	Glutathione peroxidase 3	Enzyme	P22352	Homo sapiens
MMDBp0192453	Glutathione peroxidase 2	Enzyme	P18283	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004831	5-HETE	20-Hydroxy-5S-Hydroxyeicosatetraenoic Acid	Not Available	VMH	1326548 7929234
MMDBr0004832	5-HETE	20-Hydroxy-5S-Hydroxyeicosatetraenoic Acid	cytochrome P450, family 4, subfamily F, polypeptide 2	VMH	1326548 7929234
MMDBr0004833	5-HETE	5,15-Dihydroxyeicosatetraenoic Acid	Not Available	VMH	1326548 7929234
MMDBr0004834	5-HETE	5,15-Dihydroxyeicosatetraenoic Acid	arachidonate 5-lipoxygenase	VMH	1326548 7929234
MMDBr0004835	5-HETE	5-Oxo-(6E,8Z,11Z,14Z)-Eicosatetraenoic Acid	carbonyl reductase 1	VMH	1326548 7929234
MMDBr0004836	5-HETE	5-Oxo-(6E,8Z,11Z,14Z)-Eicosatetraenoic Acid	dehydrogenase/reductase (SDR family) member 4	VMH	1326548 7929234
MMDBr0004837	5-HETE	5-Oxo-(6E,8Z,11Z,14Z)-Eicosatetraenoic Acid	dehydrogenase/reductase (SDR family) member 4	VMH	1326548 7929234
MMDBr0004890	5-HETE	Leukotriene B4	arachidonate 12-lipoxygenase	VMH	1326548 7929234
MMDBr0004891	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004892	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004893	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004894	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0009395	5(S)-Hydroperoxyeicosatetraenoic acid	5-HETE	glutathione peroxidase 1	VMH; KEGG	30371894
MMDBr0009397	5(S)-Hydroperoxyeicosatetraenoic acid	5-HETE	glutathione peroxidase 1	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Asthma	Association	Human Blood	HMDB	10361015
Rheumatoid arthritis	Association	Human Blood	HMDB	10361015
Rhinitis	Association	Human Blood	HMDB	10361015

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	1.605	0.209	uM	Adult (>18 years old)	Both	Asthma	HMDB	10361015
Human Blood	Detected and Quantified	0.600	0.097	uM	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	10361015
Human Blood	Detected and Quantified	0.787	0.056	uM	Adult (>18 years old)	Both	Rhinitis	HMDB	10361015
Human Blood	Detected and Quantified	0.000901	0.000029	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.00102	0.00079	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.001598	0.000958	uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	0.001598	0.000958	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.0119	0.0014	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.07	0.02	uM	Adult (>18 years old)	Both	Normal	HMDB	3432563
Human Blood	Detected and Quantified	0.159	0.037	uM	Adult (>18 years old)	Both	Normal	HMDB	10361015
Human Blood	Detected and Quantified	0.25	0.09	uM	Adult (>18 years old)	Both	Normal	HMDB	3432563
Human Blood	Detected and Quantified	3.51	0.57	uM	Adult (>18 years old)	Both	Normal	HMDB	3432563
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00039	0.00016	uM	Adult (>18 years old)	Both	Normal	HMDB	John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0011134

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Hydroxyeicosatetraenoic_acid

METLIN ID

6554

PubChem Compound

5280733

PDB ID

Not Available

ChEBI ID

28209

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hosni M, Meskini N, Prigent AF, Anker G, Joulain C, el Habib R, Lagarde M: Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity. Biochem Pharmacol. 1992 Mar 17;43(6):1319-29. doi: 10.1016/0006-2952(92)90509-h. [PubMed:1314059 ]
Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S. [PubMed:1672136 ]
Sud'ina GF, Kobel'kov GM, Barskii OA, Varfolomeev SD: [A kinetic scheme of human neutrophil 5-lipoxygenase activity]. Biokhimiia. 1990 Oct;55(10):1795-811. [PubMed:1964097 ]
Brinkman HJ, van Buul-Wortelboer MF, van Mourik JA: Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation. Exp Cell Res. 1991 Jan;192(1):87-92. doi: 10.1016/0014-4827(91)90161-m. [PubMed:1984423 ]
Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54. [PubMed:2550547 ]
Hoffman T, Lizzio EF, Suissa J, Rotrosen D, Sullivan JA, Mandell GL, Bonvini E: Dual stimulation of phospholipase activity in human monocytes. Role of calcium-dependent and calcium-independent pathways in arachidonic acid release and eicosanoid formation. J Immunol. 1988 Jun 1;140(11):3912-8. [PubMed:2836505 ]
Dahinden CA, Clancy RM, Gross M, Chiller JM, Hugli TE: Leukotriene C4 production by murine mast cells: evidence of a role for extracellular leukotriene A4. Proc Natl Acad Sci U S A. 1985 Oct;82(19):6632-6. doi: 10.1073/pnas.82.19.6632. [PubMed:2995976 ]
Kanaji K, Okuma M, Sugiyama T, Sensaki S, Ushikubi F, Uchino H: Requirement of free arachidonic acid for leukotriene B4 biosynthesis by 12-hydroperoxyeicosatetraenoic acid-stimulated neutrophils. Biochem Biophys Res Commun. 1986 Jul 31;138(2):589-95. doi: 10.1016/s0006-291x(86)80537-x. [PubMed:3017333 ]
Kragballe K, Desjarlais L, Duell EA, Voorhees JJ: In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis. J Invest Dermatol. 1986 Jul;87(1):47-52. doi: 10.1111/1523-1747.ep12523561. [PubMed:3088130 ]
Marcus AJ, Safier LB, Broekman MJ, Ullman HL, Islam N, Sorrell TC, Serhan CN, Weissmann G, Oglesby TD, Gorman RR: Production of metabolic products of arachidonic acid during cell-cell interactions. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 2):338-42. doi: 10.1016/0091-6749(84)90126-x. [PubMed:6088611 ]
Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5. doi: 10.1038/288183a0. [PubMed:6253824 ]
Pawlowski NA, Kaplan G, Hamill AL, Cohn ZA, Scott WA: Arachidonic acid metabolism by human monocytes. Studies with platelet-depleted cultures. J Exp Med. 1983 Aug 1;158(2):393-412. doi: 10.1084/jem.158.2.393. [PubMed:6411852 ]
Sasaki T, Asano T, Takakura K, Sano K, Nakamura T, Suzuki N, Imabayashi S, Ishikawa Y: [Cerebral vasospasm and lipid peroxidation--lipid peroxides in the cerebrospinal fluid after subarachnoid hemorrhage]. No To Shinkei. 1982 Dec;34(12):1191-6. [PubMed:7159548 ]
Maderna P, Colli S, Caruso D, Eligini S, Toia A, Galli G, Tremoli E: Quantitative changes of hydroxyacid formation during platelet-neutrophil interaction. J Lab Clin Med. 1993 Mar;121(3):406-14. [PubMed:8383163 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Chabannes B, Poubelle PE, Moliere P, De Medicis R, Lussier A, Lagarde M: Platelets abrogate leukotriene B(4) generation by human blood neutrophils stimulated with monosodium urate monohydrate or f-Met-Leu-Phe in vitro. Lab Invest. 2003 Apr;83(4):491-9. doi: 10.1097/01.lab.0000062855.90029.d8. [PubMed:12695552 ]
Powell WS, Rokach J: Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Prog Lipid Res. 2005 Mar-May;44(2-3):154-83. doi: 10.1016/j.plipres.2005.04.002. Epub 2005 Apr 20. [PubMed:15893379 ]
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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 5-HETE (MMDBc0000638)

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