Geldanamycin

Molecular Formula

C29H40N2O9

M.W.

560.60

CAS number

30562-34-6

MSDS

Download

Details

Source

Streptomyces Hygroscopicus var Geldanus

Fermentek product Code

GEL-001

Brand/grade

For research

Specifications

Appearance

Yellow solid

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

Single spot on TLC plates, by multiple methods.

Melting point

260°C-268°C

Crystallinity

Amorphous

Solubility test

Clear yellow solution at 10 mg/ml in DMSO ; Clear yellow solution at 5 mg/ml in Dichloromethane

Chemical identification

Names and identifiers

RTECS LX8920000

IUPAC Name : [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate I

Description

Geldanamycin is a benzoquinone ansamycin antibiotic, which binds to Hsp90 (Heat Shock Protein 90) and alters its function. Geldanamycin is a natural product from which several valuable derivates were synthesized. All derivates share its HSP90 inhibition, and vary in overall toxicity and water solubility.

InChl Key

QTQAWLPCGQOSGP-KSRBKZBZSA-N

Canonical SMILES

CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC

Isomeric 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

Further Information

Solubility ( literature )

Geldanamycin is soluble in DMSO, Dichloromethane. Geldanamycin is insoluble in water.

Compound Classification

Benzoquinone ansamycin antibiotic ;

HSP90 inhibitor ;