(4E,6Z,8R,9S,10E,12S,13R,14R,16R)-19-amino-9,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaene-3,20,22-trione

• ChemBase ID: 166153
• Molecular Formular: C27H38N2O7
• Molecular Mass: 502.59982
• Monoisotopic Mass: 502.26790157
• 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)O)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)O)OC)/C
• InChI: InChI=1S/C27H38N2O7/c1-14-10-18-23(28)20(30)13-19(26(18)33)29-27(34)15(2)8-7-9-21(35-5)24(31)16(3)12-17(4)25(32)22(11-14)36-6/h7-9,12-14,17,21-22,24-25,31-32H,10-11,28H2,1-6H3,(H,29,34)/b9-7-,15-8+,16-12+/t14-,17+,21-,22-,24+,25-/m1/s1
• InChIKey: FQHAJOLMHIBHDX-MLYHDKONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E,6Z,8R,9S,10E,12S,13R,14R,16R)-19-amino-9,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaene-3,20,22-trione
• IUPAC Traditional name: (4E,6Z,8R,9S,10E,12S,13R,14R,16R)-19-amino-9,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaene-3,20,22-trione
• Synonyms: 17-Amino-7-O-de(aminocarbonyl)-17-demethoxy-geldanamycin; 17-Amino-7-decarbamoyl Geldanamycin; 7-Descarbamoyl 17-Amino Geldanamycin

Database IDs

• CAS Number: 169564-26-5
• PubChem SID: 162260286
• PubChem CID: 71315585

CALCULATED PROPERTIES

• Acid pKa: 12.710763
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.2936016
• LogD (pH = 7.4): 1.2936045
• Log P: 1.2936065
• Molar Refractivity: 141.7574 cm^3
• Polarizability: 52.94294 Å^3
• Polar Surface Area: 148.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Purple Solid

DETAILS

Toronto Research Chemicals - D288835

An intermediate in the preparation of 17-(Allylamino)geldanamycin (17AAG) metabolites

REFERENCES

• Schnur, R., et al.: J. Med. Chem., 38, 3813 (1995)
• Rastelli, G., et al.: Bioorg. Med. Chem. Lett., 15, 5016 (1995)