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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 23:21:17 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006111

Secondary Accession Numbers

HMDB0004698
HMDB04698
HMDB06111

Metabolite Identification

Common Name

12-HETE

Description

12-Hydroxyeicosatetraenoic acid (CAS: 71030-37-0), also known as 12-HETE, is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with the pathogenesis of hypertension and may mediate angiotensin II and TGFbeta induced mesangial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contributes to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products (PMID: 7562532 , 12480795 , 17361113 , 8498970 , 1333255 , 2119633 ). 12-HETE is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumour cell metastatic potential through activation of protein kinase C. 12-HETE has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation. 12-HETE is found to be associated with peroxisomal biogenesis defect and Zellweger syndrome, which are inborn errors of metabolism.

Structure

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

HMDB0006111
     RDKit          3D
12-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.3530    1.0402    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5888    0.2212   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9951    1.1751   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2100    0.5692   -2.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.1896   -1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527    0.6361   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.4090    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   -0.7043    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -1.5196    1.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2540   -2.5799    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -0.6299    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830   -0.6055    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    0.2738    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    0.3585    2.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -0.3815    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.2218    1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751   -1.0199    0.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.0328    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4577   -0.4793   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7193    0.7413   -2.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2756    0.4091   -3.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4799   -0.7932   -3.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5753    1.3912   -4.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7833    1.9562    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571    0.3963    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556    1.3279    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474   -0.4596   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -0.3956    0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8470    1.7669   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963    1.9732   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.3515   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8664   -0.1849   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -0.6176   -2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689   -1.0177   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033    1.5376   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    1.1100    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -0.2780    2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694   -1.4337    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.9609    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -2.5559    3.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.0092    2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.2371    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.8954    3.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2017    1.0597    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -1.1322    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366    0.2210    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -2.0384    2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.6921    1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055    0.8523   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133    0.5584    0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4559   -0.9555   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -1.2223   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452    1.2968   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715    1.4371   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1914    2.3176   -4.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 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


  Mrv1652309201918022D          

 23 22  0  0  0  0            999 V2000
10007.428510006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.143910006.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10008.859410006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.572710006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.399510006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.112810006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.828210006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.541610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.257110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.974510006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.143910005.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.715110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.000110006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.174810006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.460110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.745610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.920110006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.205610006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.491110006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.776410006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.061610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.344910006.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.061610007.6707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  2 11  1  6  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006111

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

> <INCHI_KEY>
ZNHVWPKMFKADKW-LQWMCKPYSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.44468398364285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720826396394717

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889630645050488

> <JCHEM_PKA_STRONGEST_BASIC>
-1.608710672078515

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.4695

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12S-hete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006111
     RDKit          3D
12-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.3530    1.0402    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5888    0.2212   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9951    1.1751   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2100    0.5692   -2.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.1896   -1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527    0.6361   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.4090    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   -0.7043    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -1.5196    1.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2540   -2.5799    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -0.6299    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830   -0.6055    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    0.2738    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    0.3585    2.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -0.3815    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.2218    1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751   -1.0199    0.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.0328    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4577   -0.4793   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7193    0.7413   -2.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2756    0.4091   -3.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4799   -0.7932   -3.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5753    1.3912   -4.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7833    1.9562    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571    0.3963    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556    1.3279    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474   -0.4596   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -0.3956    0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8470    1.7669   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963    1.9732   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.3515   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8664   -0.1849   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -0.6176   -2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689   -1.0177   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033    1.5376   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    1.1100    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -0.2780    2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694   -1.4337    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.9609    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -2.5559    3.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.0092    2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.2371    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.8954    3.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2017    1.0597    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -1.1322    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366    0.2210    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -2.0384    2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.6921    1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055    0.8523   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133    0.5584    0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4559   -0.9555   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -1.2223   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452    1.2968   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715    1.4371   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1914    2.3176   -4.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 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                                 20-SEP-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-SEP-19         0                                  
HETATM    1  C   UNK     0    8680.5338679.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8681.8698678.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8683.2048679.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8684.5368678.677   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8686.0798678.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8687.4118679.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8688.7468678.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8690.0788679.446   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8691.4138678.677   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8692.7528679.446   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8681.8698677.136   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8679.2028678.677   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8677.8678679.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.3268679.446   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8674.9928678.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.6588679.446   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8672.1188679.446   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.7848678.677   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.4508679.446   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.1168678.677   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.7828679.446   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8665.4448678.677   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8666.7828680.985   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3   11                                                  
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                                                            
CONECT   11    2                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0006111
HETATM    1  C1  UNL     1      -7.353   1.040   0.928  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.589   0.221  -0.122  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.995   1.175  -1.108  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.210   0.569  -2.213  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.004  -0.190  -1.730  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.053   0.636  -0.999  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.658   0.409   0.224  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.089  -0.704   1.072  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.848  -1.520   1.466  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.254  -2.580   2.274  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.877  -0.630   2.138  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.383  -0.606   1.722  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.317   0.274   2.395  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.581   0.359   2.047  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.236  -0.381   0.977  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.361  -1.222   1.431  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.575  -1.020   0.986  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.888   0.033   0.032  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.458  -0.479  -1.279  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.719   0.741  -2.136  1.00  0.00           C  
HETATM   21  C20 UNL     1       7.276   0.409  -3.446  1.00  0.00           C  
HETATM   22  O2  UNL     1       7.480  -0.793  -3.737  1.00  0.00           O  
HETATM   23  O3  UNL     1       7.575   1.391  -4.354  1.00  0.00           O  
HETATM   24  H1  UNL     1      -7.783   1.956   0.485  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.157   0.396   1.350  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.656   1.328   1.740  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.347  -0.460  -0.599  1.00  0.00           H  
HETATM   28  H5  UNL     1      -5.861  -0.396   0.410  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.847   1.767  -1.565  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.396   1.973  -0.592  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.928   1.351  -2.948  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.866  -0.185  -2.721  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.459  -0.618  -2.620  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.369  -1.018  -1.124  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.603   1.538  -1.478  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.919   1.110   0.706  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.482  -0.278   2.020  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.769  -1.434   0.635  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.407  -1.961   0.546  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.767  -2.556   3.132  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.188  -0.009   2.955  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.648  -1.237   0.905  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.947   0.895   3.232  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.202   1.060   2.626  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.470  -1.132   0.583  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.437   0.221   0.070  1.00  0.00           H  
HETATM   47  H24 UNL     1       4.183  -2.038   2.158  1.00  0.00           H  
HETATM   48  H25 UNL     1       6.381  -1.692   1.368  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.205   0.852  -0.107  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.813   0.558   0.486  1.00  0.00           H  
HETATM   51  H28 UNL     1       7.456  -0.956  -1.100  1.00  0.00           H  
HETATM   52  H29 UNL     1       5.835  -1.222  -1.765  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.745   1.297  -2.265  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.372   1.437  -1.558  1.00  0.00           H  
HETATM   55  H32 UNL     1       7.191   2.318  -4.352  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   43
CONECT   14   15   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

HMDB0006111
     RDKit          3D
12-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.3530    1.0402    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5888    0.2212   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9951    1.1751   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2100    0.5692   -2.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.1896   -1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527    0.6361   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.4090    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   -0.7043    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481   -1.5196    1.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2540   -2.5799    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -0.6299    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830   -0.6055    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    0.2738    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    0.3585    2.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -0.3815    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.2218    1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751   -1.0199    0.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.0328    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4577   -0.4793   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7193    0.7413   -2.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2756    0.4091   -3.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4799   -0.7932   -3.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5753    1.3912   -4.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7833    1.9562    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571    0.3963    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556    1.3279    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474   -0.4596   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611   -0.3956    0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8470    1.7669   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963    1.9732   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.3515   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8664   -0.1849   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587   -0.6176   -2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689   -1.0177   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033    1.5376   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    1.1100    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -0.2780    2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694   -1.4337    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.9609    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -2.5559    3.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -0.0092    2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.2371    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.8954    3.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2017    1.0597    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -1.1322    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366    0.2210    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -2.0384    2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.6921    1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055    0.8523   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133    0.5584    0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4559   -0.9555   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -1.2223   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452    1.2968   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715    1.4371   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1914    2.3176   -4.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 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
(12S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid	ChEBI
(5Z,8Z,10E,12S,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acid	ChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acid	ChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyicosa-5,8,10,14-tetraenoic acid	ChEBI
12(S)-Hydroxy-5(Z),8(Z),10(e),14(Z)-eicosatetraenoic acid	ChEBI
12(S)-Hydroxy-5,8,14(Z),10(e)-eicosatetraenoic acid	ChEBI
12(S)-Hydroxyeicosatetraenoic acid	ChEBI
12S-HETE	ChEBI
(12S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoate	Generator
(5Z,8Z,10E,12S,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoate	Generator
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyeicosa-5,8,10,14-tetraenoate	Generator
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyicosa-5,8,10,14-tetraenoate	Generator
12(S)-Hydroxy-5(Z),8(Z),10(e),14(Z)-eicosatetraenoate	Generator
12(S)-Hydroxy-5,8,14(Z),10(e)-eicosatetraenoate	Generator
12(S)-Hydroxyeicosatetraenoate	Generator
(5Z,8Z,10E,14Z)-12-Hydroxy-5,8,10,14-eicosatetraenoic acid	HMDB
12(S)-HETE	HMDB
12(S)-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid	HMDB
12-Hydroxy-5,8,10,14-eicosatetraenoic acid	HMDB
12-Hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid	HMDB
12-Hydroxyeicosatetraenoic acid	HMDB
12-L-Hydroxy-5,8,10,14-eicosatetraenoic acid	HMDB
12S-Hydroxy-5,8,10,14-(Z,Z,e,Z)-eicosatetraenoic acid	HMDB
FA(20:4(5Z,8Z,10E,12-OH,14Z))	HMDB
FA(20:4(5Z,8Z,10E,12S-OH,14Z))	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

Traditional Name

12S-hete

CAS Registry Number

54397-83-0

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

InChI Key

ZNHVWPKMFKADKW-LQWMCKPYSA-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:34146 )
(5Z,8Z,10E,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid (CHEBI:34146 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14777 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0061118)

Source

Exogenous

Exogenous (HMDB: HMDB0061118)

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	0.0017 g/L	ALOGPS
logP	5.86	ALOGPS
logP	5.36	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.89	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	38.44 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
DeepCCS	[M+H]+	192.929	30932474
DeepCCS	[M-H]-	190.571	30932474
DeepCCS	[M-2H]-	223.457	30932474
DeepCCS	[M+Na]+	199.022	30932474
AllCCS	[M+H]+	186.9	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.6	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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	21.1491 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O	4158.6	Standard polar	33892256
12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O	2420.8	Standard non polar	33892256
12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O	2593.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12-HETE,1TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2737.0	Semi standard non polar	33892256
12-HETE,1TMS,isomer #2	CCCCC/C=C\C[C@H](O)/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2633.5	Semi standard non polar	33892256
12-HETE,2TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2706.2	Semi standard non polar	33892256
12-HETE,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2983.3	Semi standard non polar	33892256
12-HETE,1TBDMS,isomer #2	CCCCC/C=C\C[C@H](O)/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2875.1	Semi standard non polar	33892256
12-HETE,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H](/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	3192.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0526 +/- 0.0944 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	0.35 +/- 0.25 uM	Adult (>18 years old)	Both	Normal	3432563	details
Blood	Detected and Quantified	0.00422 +/- 0.000292 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.00642 +/- 0.00074 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00395 +/- 0.0033 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00091 +/- 0.00031 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 0.001 uM	Adult (>18 years old)	Both	Normal	15910986	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	0-1.560e-08 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8825400	details
Urine	Detected and Quantified	0-0.00000001560 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8825400	details
Urine	Detected and Quantified	0.000012138 +/- 0.0000035633 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	15882928	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cerebral Vasospasm	15910986	details
Urine	Detected and Quantified	0.000000078 (0.00-0.000000156) umol/mmol creatinine	Adult (>18 years old)	Both	Peroxisomal biogenesis defect	MetaGene: Metabol...	details
Urine	Detected and Quantified	0.00001248 (0.0000090000-0.00001903) umol/mmol creatinine	Infant (0-1 year old)	Both	Zellweger syndrome	8825400	details

Associated Disorders and Diseases

Disease References

Cerebral vasospasm
Poloyac SM, Reynolds RB, Yonas H, Kerr ME: Identification and quantification of the hydroxyeicosatetraenoic acids, 20-HETE and 12-HETE, in the cerebrospinal fluid after subarachnoid hemorrhage. J Neurosci Methods. 2005 Jun 15;144(2):257-63. Epub 2004 Dec 30. [PubMed:15910986 ]
Peroxisomal biogenesis defect
Mayatepek E, Lehmann WD: 12- and 15-hydroxyeicosatetraenoic acid are excreted in the urine of peroxisome-deficient patients: evidence for peroxisomal metabolism in vivo. Pediatr Res. 1996 Jan;39(1):146-9. [PubMed:8825400 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.

Associated OMIM IDs

214100 (Peroxisomal biogenesis defect)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000424

Chemspider ID

4446279

KEGG Compound ID

C14777

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

12-Hydroxyeicosatetraenoic acid

METLIN ID

Not Available

PubChem Compound

5283155

PDB ID

Not Available

ChEBI ID

34146

Food Biomarker Ontology

Not Available

VMH ID

12HARACHD

MarkerDB ID

MDB00000482

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Diaz A, Ruiz F, Florez J, Hurle MA, Pazos A: Mu-opioid receptor regulation during opioid tolerance and supersensitivity in rat central nervous system. J Pharmacol Exp Ther. 1995 Sep;274(3):1545-51. [PubMed:7562532 ]
Simopoulos AP: Omega-3 fatty acids in inflammation and autoimmune diseases. J Am Coll Nutr. 2002 Dec;21(6):495-505. [PubMed:12480795 ]
Hao CM, Breyer MD: Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney Int. 2007 Jun;71(11):1105-15. Epub 2007 Mar 14. [PubMed:17361113 ]
Schror K: Prostaglandin-mediated actions of the renin-angiotensin system. Arzneimittelforschung. 1993 Feb;43(2A):236-41. [PubMed:8498970 ]
Ruzicka T: The role of the epidermal 12-hydroxyeicosatetraenoic acid receptor in the skin. Eicosanoids. 1992;5 Suppl:S63-5. [PubMed:1333255 ]
Schror K: Platelet reactivity and arachidonic acid metabolism in type II hyperlipoproteinaemia and its modification by cholesterol-lowering agents. Eicosanoids. 1990;3(2):67-73. [PubMed:2119633 ]
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 ]

Showing metabocard for 12-HETE (HMDB0006111)

MOL for HMDB0006111 (12-HETE)

3D MOL for HMDB0006111 (12-HETE)

3D SDF for HMDB0006111 (12-HETE)

3D-SDF for HMDB0006111 (12-HETE)

PDB for HMDB0006111 (12-HETE)

3D PDB for HMDB0006111 (12-HETE)

SMILES for HMDB0006111 (12-HETE)

INCHI for HMDB0006111 (12-HETE)

Structure for HMDB0006111 (12-HETE)

3D Structure for HMDB0006111 (12-HETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized