(4E,6Z,8R,9S,10E,12S,13R,14R,16R)-19-amino-13-hydroxy-8,14-dimethoxy-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: 160099
• Molecular Formular: C28H39N3O8
• Molecular Mass: 545.62456
• Monoisotopic Mass: 545.27371522
• 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)N
• Canonical SMILES: CO[C@@H]1C[C@H](C)CC2=C(N)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/C28H39N3O8/c1-14-10-18-23(29)20(32)13-19(25(18)34)31-27(35)15(2)8-7-9-21(37-5)26(39-28(30)36)17(4)12-16(3)24(33)22(11-14)38-6/h7-9,12-14,16,21-22,24,26,33H,10-11,29H2,1-6H3,(H2,30,36)(H,31,35)/b9-7-,15-8+,17-12+/t14-,16+,21-,22-,24-,26+/m1/s1
• InChIKey: XYFFWTYOFPSZRM-IPQLZRNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E,6Z,8R,9S,10E,12S,13R,14R,16R)-19-amino-13-hydroxy-8,14-dimethoxy-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)-19-amino-13-hydroxy-8,14-dimethoxy-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: 17-Amino-17-demethoxygeldanamycin; 17-Aminogeldanamycin; NSC 255109; 17AG; 17-Amino Geldanamycin

Database IDs

• CAS Number: 64202-81-9
• PubChem SID: 162254234
• PubChem CID: 71313226

CALCULATED PROPERTIES

• Acid pKa: 12.77528
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.4011816
• LogD (pH = 7.4): 1.4011847
• Log P: 1.4011863
• Molar Refractivity: 149.5856 cm^3
• Polarizability: 56.106083 Å^3
• Polar Surface Area: 180.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Dark Purple Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A609700

The active metabolite of 17-(Allylamino)geldanamycin (17AAG).

REFERENCES

• Kamal, A., et al.: Nature, 425, 407 (2003)
• Goetz, M., et al.: J. Clin. Oncol., 23, 1078 (2003)
• Bagatell, R., et al.: Clin. Cancer Res., 13, 1783 (2003)
• Burger, A., et al.: Cancer Lett., 245, 11 (2003)