prop-2-en-1-yl 4-[5-(4-fluorophenyl)-5-hydroxy-4-phenyl-2-(phenylcarbamoyl)-1-(propan-2-yl)-3,10-dioxa-6-azatricyclo[4.4.0.02,4]decan-9-yl]-3-hydroxybutanoate

• ChemBase ID: 159674
• Molecular Formular: C36H39FN2O7
• Molecular Mass: 630.7024632
• Monoisotopic Mass: 630.27412982
• SMILES: C12(C(C(N3C1(OC(CC3)CC(CC(=O)OCC=C)O)C(C)C)(c1ccc(cc1)F)O)(O2)c1ccccc1)C(=O)Nc1ccccc1
• Canonical SMILES: C=CCOC(=O)CC(CC1CCN2C(O1)(C(C)C)C1(OC1(C2(O)c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1)O
• InChI: InChI=1S/C36H39FN2O7/c1-4-21-44-31(41)23-29(40)22-30-19-20-39-35(43,26-15-17-27(37)18-16-26)33(25-11-7-5-8-12-25)34(46-33,36(39,45-30)24(2)3)32(42)38-28-13-9-6-10-14-28/h4-18,24,29-30,40,43H,1,19-23H2,2-3H3,(H,38,42)
• InChIKey: NCWKXXNHQXONBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl 4-[5-(4-fluorophenyl)-5-hydroxy-4-phenyl-2-(phenylcarbamoyl)-1-(propan-2-yl)-3,10-dioxa-6-azatricyclo[4.4.0.0^2,^4]decan-9-yl]-3-hydroxybutanoate
• IUPAC Traditional name: prop-2-en-1-yl 4-[5-(4-fluorophenyl)-5-hydroxy-1-isopropyl-4-phenyl-2-(phenylcarbamoyl)-3,10-dioxa-6-azatricyclo[4.4.0.0^2,^4]decan-9-yl]-3-hydroxybutanoate
• Synonyms: 7-(4-Fluorophenyl)hexahydro-β,7-dihydroxy-1b-(1-methylethyl)-7a-phenyl-1a-[(phenylamino)carbonyl]-3H-oxireno[3,4]pyrrolo[2,1-b][1,3]oxazine-3-butanoic Acid Allyl Ester; Allyl-ATV-cycloIP; Allyl Ester of Atorvastatin Cyclic (Isopropyl) Impurity; 17-Demethoxy-17-(2-propenylamino)geldanamycin; 17-(Allylamino)-17-demethoxygeldanamycin; 17-(Allylamino)-17-desmethylgeldanamycin; 17-Demethoxy-17-allylaminogeldanamycin; 17AAG; CP 127374; KOS 953; NSC 330507; Tanespimycin; 17-AAG; 17-(Allylamino) Geldanamycin

Database IDs

• CAS Number: 75747-14-7; 1316295-72-3
• PubChem SID: 162253809
• PubChem CID: 71313087

CALCULATED PROPERTIES

• Acid pKa: 11.187202
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 5.950142
• LogD (pH = 7.4): 6.0571156
• Log P: 6.058739
• Molar Refractivity: 169.1028 cm^3
• Polarizability: 66.01912 Å^3
• Polar Surface Area: 117.56 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Dark Purple Solid
• Melting Point: >194°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A791835

Intermediate in the preparation of Atorvastatin degradation products.

Toronto Research Chemicals - A549650

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)