MiMeDB: Showing metabocard for 12-HETE (MMDBc0000439)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:47 UTC

Update Date

2024-04-30 19:32:25 UTC

Metabolite ID

MMDBc0000439

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>
MMDBc0000439

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₀H₃₂O₃

Average Mass

320.4663

Monoisotopic Mass

320.23514489

IUPAC Name

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

Traditional Name

12S-hete

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lxy-8892000000-af669345c2f07af6464f	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0149000000-30d66ea8fabdf9ad8be7	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-1170-5894000000-a08e2339ff5012eb70cb	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9630000000-1125d69108467f1388e5	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-a230e97019aecf4548b9	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uxr-1249000000-3b11e114d7aa3c180372	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9820000000-08efc5f37c4b2f87360c	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-9fc7e9714470f0f9624f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-0419000000-cd9d67d0c1bba959fe5c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9581000000-d70c346b7a187ee4a266	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0349000000-af69d38890bc80fda3a3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-5932000000-f79082fedeb294426f6f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9410000000-8748c14268773fb5c2fd	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	242.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	33.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	708.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	555.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	977.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	414.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3120.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	108.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	493.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	781.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	495.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	268.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	201.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	338.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	622.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	491.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1683.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2054.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	12-HETE_TMS_1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	standard non polar	2025-10-23	1524.62
Gas Chromatography	12-HETE_TMS_2	CCCCC/C=C\C[C@H](O)/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2757.57
Gas Chromatography	12-HETE_TMS_3	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	standard non polar	2025-10-23	2823.69
Gas Chromatography	12-HETE_TMS_1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	standard polar	2025-10-23	2009.04
Gas Chromatography	12-HETE_TMS_2	CCCCC/C=C\C[C@H](O)/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	standard polar	2025-10-23	1262.49
Gas Chromatography	12-HETE_TMS_3	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	standard polar	2025-10-23	1448.99

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Saliva
Urine

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.00001248		0.0000090000	0.00001903	umol/mmol creatinine	Infant (0-1 year old)	Both	Zellweger syndrome	HMDB	8825400
Human Urine	Detected and Quantified			0	0.00000001560	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8825400
Human Urine	Detected and Quantified			0	1.560e-08	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8825400
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	15910986
Human Urine	Detected and Quantified	0.000012138	0.0000035633			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	15882928
Human Blood	Detected and Quantified	0.00395	0.0033			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.00422	0.000292			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.00642	0.00074			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.0526	0.0944			uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	0.35	0.25			uM	Adult (>18 years old)	Both	Normal	HMDB	3432563
Human Urine	Detected and Quantified	0.000000078		0.00	0.000000156	umol/mmol creatinine	Adult (>18 years old)	Both	Peroxisomal biogenesis defect	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00091	0.00031			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
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371

External Links

HMDB ID

HMDB0006111

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

CMMC Knowledgebase

Not Available

General References

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 ]
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 ]
Schror K: Prostaglandin-mediated actions of the renin-angiotensin system. Arzneimittelforschung. 1993 Feb;43(2A):236-41. [PubMed:8498970 ]
Simopoulos AP: Omega-3 fatty acids in inflammation and autoimmune diseases. J Am Coll Nutr. 2002 Dec;21(6):495-505. doi: 10.1080/07315724.2002.10719248. [PubMed:12480795 ]
Hao CM, Breyer MD: Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney Int. 2007 Jun;71(11):1105-15. doi: 10.1038/sj.ki.5002192. Epub 2007 Mar 14. [PubMed:17361113 ]
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 (MMDBc0000439)

MOL for #<Metabolite:0x00007f9aa83926d8>

3D MOL for #<Metabolite:0x00007f9aa83926d8>

3D SDF for #<Metabolite:0x00007f9aa83926d8>

3D-SDF for #<Metabolite:0x00007f9aa83926d8>

PDB for #<Metabolite:0x00007f9aa83926d8>

3D PDB for #<Metabolite:0x00007f9aa83926d8>

SMILES for #<Metabolite:0x00007f9aa83926d8>

INCHI for #<Metabolite:0x00007f9aa83926d8>

Structure for #<Metabolite:0x00007f9aa83926d8>

3D Structure for #<Metabolite:0x00007f9aa83926d8>