(4E,6Z,8R,9S,10E,12S,13R,14R,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-[(prop-2-en-1-yl)amino]-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate

• ChemBase ID: 159675
• Molecular Formular: C31H43N3O8
• Molecular Mass: 585.68842
• Monoisotopic Mass: 585.30501535
• 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)NCC=C
• Canonical SMILES: C=CCNC1=C2C[C@@H](C)C[C@@H](OC)[C@H](O)[C@@H](C)/C=C(\C)/[C@@H]([C@@H](/C=C\C=C(\C(=O)NC(=CC1=O)C2=O)/C)OC)OC(=O)N
• InChI: 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
• InChIKey: AYUNIORJHRXIBJ-WHCYGHKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E,6Z,8R,9S,10E,12S,13R,14R,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-[(prop-2-en-1-yl)amino]-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-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-en-1-ylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
• Synonyms: 17-Demethoxy-17-(2-propenylamino-d5)geldanamycin; 17-(Allylamino-d5)-17-demethoxygeldanamycin; 17-(Allylamino-d5)-17-desmethylgeldanamycin; 17-Demethoxy-17-(allylamino-d5)geldanamycin; 17AAG-d5; CP 127374-d5; KOS 953-d5; NSC 330507-d5; Tanespimycin-d5; 17-(Allylamino-d5) Geldanamycin

Database IDs

• PubChem SID: 162253810
• PubChem CID: 71313088

CALCULATED PROPERTIES

• Acid pKa: 12.775146
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.5650165
• LogD (pH = 7.4): 2.565015
• Log P: 2.5650165
• Molar Refractivity: 163.5229 cm^3
• Polarizability: 61.361977 Å^3
• Polar Surface Area: 166.28 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Purple Solid
• Melting Point: 161-163°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A549652

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.

REFERENCES

• Schnur, R.C., et al.: J. Med. Chem., 38, 3806 (1995)
• Nimmanapalli, R., et al.: Cancer Res., 61, 1799 (1995)
• Basso, A.D., et al.: Oncogene, 21, 1159 (1995)