(4Z,6Z,8S,9S,10Z,12S,13R,14S,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: 131732
• Molecular Formular: C29H40N2O9
• Molecular Mass: 560.6359
• Monoisotopic Mass: 560.27338087
• SMILES: C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(\[C@@H]([C@H](/C=C\C=C(/C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)\C)OC)OC(=O)N)/C)C)O)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-BMBHCMFXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4Z,6Z,8S,9S,10Z,12S,13R,14S,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: (4Z,6Z,8S,9S,10Z,12S,13R,14S,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: Geldanamycin from Streptomyces hygroscopicus

Database IDs

• CAS Number: 30562-34-6
• MDL Number: MFCD00274570
• PubChem SID: 162226009
• PubChem CID: 24870960

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: DMSO: soluble
• Apperance: yellow to orange powder

Safety Information

• RTECS: LX8920000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - G3381

Biochem/physiol Actions
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 of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.

Sigma Aldrich - G153

Biochem/physiol Actions
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 of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.