12(S)-HPETE - Moligand™,≥98%,100 μg/ml in ethanol , Activator of TRPV1, CAS No.71774-10-2, Activator of TRPV1

CAS: 71774-10-2 Cat. No.: H336047 Molecular Weight: 336.47

GRADE & PURITY Moligand™, ≥98%, 100 μg/ml in ethanol

Synonyms

UNII-54G1W9LPV0 | 12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid | (5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoate | omega-9 Hpaa | NCGC00161250-01 | 12(S)-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid | 12-Hydroperoxyicosatetraenoa

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

12(S)-HPETE is a monoperoxide hydrogenated polyunsaturated fatty acid produced by the action of platelet or leukocyte 12-lipoxygenase (12-LO) on arachidonic acid. It can activate leukocyte 5-LO in human blood, thereby synthesizing 5(S)-HETE, leukotriene B4, and 5(S),12(S)-DiHETE. Rat lungs metabolize 12(S)-HpETE into 8,11,12- and 10,11,12-trihydroxyphyllotrienoic acids. 12(S)-HpETE is a mediator of various biological functions, including inducing c-fos and c-jun, activating AP-1, and endothelium-dependent vasoconstriction. It mediates the inhibitory synaptic response of pyramidal sensory neurons to FMRF-amide and is a potent selective inhibitor of Ca2+/calmodulin-dependent protein kinase II in the rat cerebral cortex. It can also inhibit thromboxane synthase and platelet aggregation by activating guanylate cyclase.

Specifications

Synonyms

UNII-54G1W9LPV0 | 12S-hydroperoxy-5Z, 8Z, 10E, 14Z-eicosatetraenoic acid | (5Z, 8Z, 10E, 14Z)-(12S)-12-Hydroperoxyicosa-5, 8, 10, 14-tetraenoate | omega-9 Hpaa | NCGC00161250-01 | 12(S)-Hydroperoxy-5Z, 8Z, 10E, 14Z-eicosatetraenoic acid | 12-Hydroperoxyicosatetraenoa

Specifications & Purity

Moligand™, ≥98%, 100 μg/ml in ethanol

Biochemical and Physiological Mechanisms

12(S)-HPETE is a 12-hydroxyeicosatetraenoic acid. 12(S)-HPETE has the function of regulating vascular tone. 12(S)-HPETE induces the expression of c-Fos and c-Jun protein and increases activating protein 1 (AP-1) activity in vascular smooth muscle cells.12

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR

Mechanism of action

Activator of TRPV1

Purity

≥98%

Product Properties

• Ki Data: Endogenous TRPV1: Ki= 0.35 μM

Names and Identifiers

• Canonical Smiles: CCCCCC=CCC(C=CC=CCC=CCCCC(=O)O)OO
• IUPAC Name: (5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
• InChIKey: ZIOZYRSDNLNNNJ-LQWMCKPYSA-N
• INCHI: 1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
• Isomeric SMILES: CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)OO
• Molecular Weight: 336.47
• Reaxy-Rn: 27577755
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27577755&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Eicosanoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Eicosanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroperoxyeicosatetraenoic acids
• Alternative Parents: Long-chain fatty acids Hydroperoxy fatty acids Unsaturated fatty acids Allylic hydroperoxides Peroxols Monocarboxylic acids and derivatives Carboxylic acids Alkyl hydroperoxides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydroperoxyeicosatetraenoic acid - Long-chain fatty acid - Hydroperoxy fatty acid - Fatty acid - Unsaturated fatty acid - Allylic hydroperoxide - Hydroperoxide - Carboxylic acid derivative - Alkyl hydroperoxide - Carboxylic acid - Peroxol - Monocarboxylic acid or derivatives - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
• External Descriptors: Hydroxy/hydroperoxyeicosatetraenoic acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (1 Activities)

Discover Target: TRPV1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (0.8 mg/ml at 25.0° C), DMSO, DMF, ethanol, pH 7.2 PBS (0.8 mg/ml), 0.1M Na2CO3 (2 mg/ml), and dimethyl formamide.
• Refractive Index: n20D1.51
• Boil Point(°C): 78° C
• Molecular Weight: 336.500 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 336.23 Da
• Monoisotopic Mass: 336.23 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 408.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1