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135304-07-3,MFCD00871540
Catalog No.:AA007ZK2

135304-07-3 | Ac-cys(farnesyl)-oh

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Purity
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1mg
≥98%
in stock  
$46.00   $32.00
- +
5mg
≥98%
in stock  
$112.00   $78.00
- +
10mg
≥98%
in stock  
$199.00   $139.00
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25mg
≥98%
in stock  
$436.00   $305.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA007ZK2
Chemical Name:
Ac-cys(farnesyl)-oh
CAS Number:
135304-07-3
Molecular Formula:
C20H33NO3S
Molecular Weight:
367.5459
MDL Number:
MFCD00871540
SMILES:
CC(=CCSC[C@@H](C(=O)O)NC(=O)C)CCC=C(CCC=C(C)C)C
Properties
Computed Properties
 
Complexity:
517  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
12  
XLogP3:
5  

Downstream Synthesis Route
66-84-2    135304-07-3   
glucosamine(R)-2-amino-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate 

[1]Patent:WO2010/90845,2010,A1.Locationinpatent:Page/Pagecolumn82

Literature

Title: N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells.

Journal: Experimental dermatology 20120901

Title: Evaluation of substrate and inhibitor binding to yeast and human isoprenylcysteine carboxyl methyltransferases (Icmts) using biotinylated benzophenone-containing photoaffinity probes.

Journal: Biochemical and biophysical research communications 20120622

Title: Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization.

Journal: Bioorganic & medicinal chemistry 20120101

Title: N-Acetylfarnesylcysteine is a novel class of peroxisome proliferator-activated receptor γ ligand with partial and full agonist activity in vitro and in vivo.

Journal: The Journal of biological chemistry 20111202

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site.

Journal: The Journal of investigative dermatology 20080301

Title: Drugs affecting prelamin A processing: effects on heterochromatin organization.

Journal: Experimental cell research 20080201

Title: Genetic and pharmacologic analyses of the role of Icmt in Ras membrane association and function.

Journal: Methods in enzymology 20060101

Title: Purification, functional reconstitution, and characterization of the Saccharomyces cerevisiae isoprenylcysteine carboxylmethyltransferase Ste14p.

Journal: The Journal of biological chemistry 20050225

Title: Carboxyl methylation of Ras regulates membrane targeting and effector engagement.

Journal: The Journal of biological chemistry 20040220

Title: Studies on G-protein alpha.betagamma heterotrimer formation reveal a putative S-prenyl-binding site in the alpha subunit.

Journal: The Biochemical journal 20031201

Title: Prenylcysteine carboxymethyltransferase type III activity is decreased in retinoic acid-treated SH-SY5Y neuroblastoma cells.

Journal: The international journal of biochemistry & cell biology 20020501

Title: Role of isoprenylcysteine carboxyl methyltransferase in tumor necrosis factor-alpha stimulation of expression of vascular cell adhesion molecule-1 in endothelial cells.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20020501

Title: Carboxyl-methylation of Rab3D in the rat pancreatic acinar tumor cell line AR42J.

Journal: Biochemical and biophysical research communications 20010720

Title: Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats.

Journal: Pharmacology, biochemistry, and behavior 20000801

Title: Dislodgment and accelerated degradation of Ras.

Journal: Biochemistry 19980203

Title: Gordon JS, et al. Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site.J Invest Dermatol. 2008 Mar;128(3):643-54. Epub 2007 Sep 20.

Title: Adhami K, et al. N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells.Exp Dermatol. 2012 Sep;21(9):700-5.

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