(4E,6Z,8R,9S,10E,12S,13R,14R,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

• ChemBase ID: 169586
• Molecular Formular: C29H40N2O9
• Molecular Mass: 560.6359
• Monoisotopic Mass: 560.27338087
• SMILES: C1(=C2C(=O)C(=CC1=O)NC(=O)/C(=C/C=C\[C@H]([C@H](/C(=C/[C@@H]([C@H]([C@@H](C[C@@H](C2)C)OC)O)C)/C)OC(=O)N)OC)/C)OC
• Canonical SMILES: CO[C@@H]1C[C@H](C)CC2=C(OC)C(=O)C=C(C2=O)NC(=O)/C(=C/C=C\[C@H]([C@H](/C(=C/[C@@H]([C@H]1O)C)/C)OC(=O)N)OC)/C
• 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-NXSHVLOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E,6Z,8R,9S,10E,12S,13R,14R,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
• IUPAC Traditional name: (4E,6Z,8R,9S,10E,12S,13R,14R,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
• Synonyms: 9,13-Dihydroxy-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 9-Carbamate; (+)-Geldanamycin; NSC 122750; NSC 212518; Geldanamycin

Database IDs

• CAS Number: 30562-34-6
• PubChem SID: 162263718
• PubChem CID: 71317043

CALCULATED PROPERTIES

• Acid pKa: 12.766906
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 2.1511946
• LogD (pH = 7.4): 2.151193
• Log P: 2.1511946
• Molar Refractivity: 152.6793 cm^3
• Polarizability: 57.511158 Å^3
• Polar Surface Area: 163.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chlorofom; DMSO
• Apperance: Yellow to Orange Solid
• Melting Point: 276-278°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G304500

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

REFERENCES

• Supko, J.G., et al.: Cancer Chemother. Pharmacol., 36, 305 (1995)
• Chavany, C., et al.: J. Biol. Chem., 271, 4974 (1995)
• Schneider, C., et al.: Proc. Natl. Acad. Sci., 93, 14536 (1995)
• Whitesell, L., et al.: Mol. Endocrinol., 10, 705 (1995)
• Stebbins, C