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17-(Allylamino)-17-demethoxygeldanamycin

SIGMA/A8476 - ≥98% (HPLC), solid

Synonym: 17-(Allylamino)geldanamycin; 17-AAG; 17-Demethoxy-17-allylamino geldanamycin; CP 127374; Geldanamycin,17-demethoxy-17-(2-propenylamino)-; NSC 330507; Tanespimycin

CAS Number: 75747-14-7
Empirical Formula (Hill Notation): C31H43N3O8
Molecular Weight: 585.69
MDL Number: MFCD04973892
Linear Formula: C31H43N3O8
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-A8476-500UG 500 µg
 $266.00
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antibiotic activity spectrum neoplastics
assay ≥98% (HPLC)
form solid
InChI 1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChI key AYUNIORJHRXIBJ-TXHRRWQRSA-N
mode of action enzyme | inhibits
Quality Level 200 
shipped in wet ice
SMILES string CO[C@H]1C[C@H](C)CC2=C(NCC=C)C(=O)C=C(NC(=O)C(C)=CC=C[C@H](OC)[C@@H](OC(N)=O)C(C)=C[C@H](C)[C@H]1O)C2=O
solubility DMSO: soluble
  methanol: soluble
storage temp. −20°C
Application: 17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) has been used as a heat shock protein 90 (HSP90) inhibitor:
• to study its effects on hippocampal neurons
• to analyze its effects on yes-associated protein (YAP) phosphorylation in adenocarcinoma human alveolar basal epithelial cells and human breast epithelial cells
• to study its effects on lifespan extension and health in Caenorhabditis elegans
Biochem/physiol Actions: 17-(Allylamino)-17-demethoxygeldanamycin (17-AAG) is a benzoquinone and is an analog of geldanamycin.
Biochem/physiol Actions: Potent inhibitor of heat shock protein 90 (Hsp90). 17-AAG is a less toxic analog than geldanamycin. It induces apoptosis and displays antitumor effects. 17-AAG inhibits the activity of oncogenic proteins such as N-ras, Ki-ras, c-Akt, and p185erB2.
Features and Benefits: This compound is a featured product for Apoptosis research. Click here  to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
General description: Chemical structure: benzenoid
Packaging: 500 μg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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