Geldanamycin

CAS: 30562-34-6

Ref. TR-G304500

Product Information

• Name: Geldanamycin
• Synonyms: [(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, (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, (8S,9S,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, 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate, 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, [8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-, 2-Azabicyclo[16.3.1]docosane, geldanamycin deriv., Brn 1633093, NSC 212518, Nsc 122750, U-29135, [8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione

Description

Applications Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines.It binds specifically to the heat shock protein Hsp90 and to its endoplasmic reticulum homologue GP96, and thus interferes with conformational maturation of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.
References Supko, J.G., et al.: Cancer Chemother. Pharmacol., 36, 305 (1995), Chavany, C., et al.: J. Biol. Chem., 271, 4974 (1996), Schneider, C., et al.: Proc. Natl. Acad. Sci., 93, 14536 (1996), Whitesell, L., et al.: Mol. Endocrinol., 10, 705 (1996), Stebbins, C.E., et al.: Cell, 89, 239 (1997),

• Brand: TRC

Chemical properties

• Molecular weight: 560.64
• Formula: C₂₉H₄₀N₂O₉
• Color/Form: Neat
• 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
• InChI key: InChIKey=QTQAWLPCGQOSGP-BMBHCMFXSA-N
• SMILES: COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O