12S-HpETE
Basic information
- CAS
71774-10-2- Standard SMILES
CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)OO- InChIKey
ZIOZYRSDNLNNNJ-LQWMCKPYSA-N- Molecular formula
- C20H32O4
- Average molar mass
- 336.5 g/mol
- Monoisotopic mass
- 336.2300595
Overview
12(S)-HPETE is the (S)-enantiomer of 12-HPETE. It has a role as a mouse metabolite. It is functionally related to an icosa-5,8,10,14-tetraenoic acid. It is a conjugate acid of a 12(S)-HPETE(1-). It is an enantiomer of a 12(R)-HPETE.
Names & identifiers
- Preferred name
- 12S-HpETE
- IUPAC
- (5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
- English name
- 12(S)-HPETE
- Molecular formula
- C20H32O4
- Molecular weight
- 336.47
Names & synonyms
12S-HpETE12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acidRefChem:105745212(S)-HPETE71774-10-212-Hpete, (S)-UNII-54G1W9LPV054G1W9LPV012-Hydroperoxyarachidonic acid, (S)-(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid12-Hydroperoxyicosatetraenoate12(S)-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
Show more names
12(S)HpETE,12(S) HpETEZIOZYRSDNLNNNJ-LQWMCKPYSA-N12(S)-HpETE(solution in ethanol)12(S)-HpETE Lipid Maps MS Standard12(S)-Hydroperoxy-eicosatetraenoic acid12(S)-hydroperoxy-5(Z),8(Z),10(E),14(Z)-ETA(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid12(S)-HYDROPEROXYEICOSA-5Z,8Z,10E,14Z-TETRAENOIC ACID
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxy-5,8,10,14-eicosatetraenoic acid5,8,10,14-Eicosatetraenoic acid, 12-hydroperoxy-, (5Z,8Z,10E,12S,14Z)-)-12(S)-HpETE Lipid Maps(R) MS Standard12-Hydroperoxyeicosatetraenoate12-Hydroperoxyicosatetraenoic acid12-Hydroperoxyeicosatetraenoic acid(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoate(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 15
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 408
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
Physical DescriptionLiquid
Physicochemical properties
- Boiling point
- 518 · 518.0±50.0 °C(Predicted)
- Density
- 1.013 · 1.013±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 0.1 M · 0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS pH 7.2: 0.8 mg/ml
- form
- Liquid.
- pka
- 4.75 · 4.75±0.10(Predicted)
- FDA UNII
- 54 G1W9LPV0 · 54G1W9LPV0
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Hazard statements
- H225-H319
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Chemistry & industry
Pharmacology
Tissue LocationsPlatelet
Cellular LocationsCytoplasm
Metabolite PathwaysAcetaminophen Action Pathway
Applications
Description12(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of platelet or leukocyte 12-lipoxygenase (12-LO) on arachidonic acid. It activates human blood leukocyte 5-LO, resulting in the synthesis of 5(S)-HETE, leukotriene B4 (LTB4), and 5(S),12(S)-DiHETE. Rat lung metabolizes 12(S)-HpETE to 8,11,12- and 10,11,12-trihydroxyeicostrienoic acids. 12(S)-HpETE is the mediator of many biological functions, including induction of c-fos and c-jun, activation of AP-1, and endothelium-dependent vasoconstriction. It mediates the inhibitory synaptic response to FMRF-amide in Aplysia sensory neurons and inhibits Ca2+/calmodulin-dependent protein kinase II from rat brain cortex.
Uses12(S)-HPETE is a fatty acid and an activator of human blood leukocyte 5-LO.
Additional notes
DefinitionChEBI: 12(S)-HPETE is the (S)-enantiomer of 12-HPETE. It has a role as a mouse metabolite. It is functionally related to an icosa-5,8,10,14-tetraenoic acid. It is a conjugate acid of a 12(S)-HPETE(1-). It is an enantiomer of a 12(R)-HPETE.
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