Geldanamycin

Category	Influenza Virus
CAS	30562-34-6
Description	Geldanamycin is a benzoquinone ansamycin antibiotic that inhibits heat shock protein 90 (HSP90). Geldanamycin has been shown to promote survival of neural stem cells from oxidative stress via inhibition of HSP90. It displays potent antineoplastic properties and inhibits myeloma cell growth.

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Product Information

Synonyms	geldanomycin; NSC 122750; [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
IUPAC Name	[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
Molecular Weight	560.64
Molecular Formula	C29H40N2O9
Canonical SMILES	CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC
InChI	InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
InChIKey	QTQAWLPCGQOSGP-KSRBKZBZSA-N
Boiling Point	627.87°C at 760 mmHg
Melting Point	252-255°C
Flash Point	427.9±32.9 °C
Purity	>98%
Density	1.2443 g/cm3
Solubility	DMSO ≥ 110mg/mL H2O < 1.2mg/mL Ethanol < 1.2mg/mL
Appearance	Solid Powder
Application	Antibiotics, Antineoplastic
Storage	3 years -20°C powder, 6 months -80°C in solvent.
Complexity	1150
Exact Mass	560.27338086
Index Of Refraction	1.559
In Vitro	Geldanamycin significantly delays and reduces viperin expression, indicating that IRF3 is involved in viperin induction in RAW264.7 cells. Geldanamycin (GA), a benzoquinone ansamycin, protected against neuronal injury induced by oxygen-glucose deprivation (OGD)/zVAD treatment in cultured primary neurons. More importantly, Geldanamycin decreases RIP1 protein level in a time and concentration-dependent manner. Geldanamycin also decreases the Hsp90 protein level, which causes instability of RIP1 protein, resulting in decreased RIP1 protein level but not RIP1 mRNA level after Geldanamycin treatment. Geldanamycin (GA) is identified as the first natural product inhibitor of Hsp90 that binds to the N-terminal ATPase domain of Hsp90 to inhibit its chaperone function, and significantly induces tumor cell death via an apoptotic mechanism.
PSA	163.48000
Target	HSP; Bacterial; Influenza Virus; Antibiotic
Vapor Pressure	0.0±6.2 mmHg at 25°C
XLogP3-AA	2