geldanamycin   Click here for help

GtoPdb Ligand ID: 9829

PDB Ligand
Compound class: Synthetic organic
Comment: Geldanamycin is a benzoquinone antibiotic that inhibits HSP90 and promotes the proteasomal degradation of oncogenic signaling proteins.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 163.48
Molecular weight 560.27
XLogP 1.02
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1CC(C)CC2=C(OC)C(=O)C=C(C2=O)NC(=O)C(=CC=CC(C(C(=CC(C1O)C)C)OC(=O)N)OC)C
Isomeric 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
InChI Key QTQAWLPCGQOSGP-KSRBKZBZSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(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
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Specialist databases
Reactome Drug Reactome logo R-ALL-1217505
Reactome Reaction Reactome logo R-HSA-1218824
Other databases
ChEMBL Ligand CHEMBL278315
GtoPdb PubChem SID 354702300
PubChem CID 5288382
RCSB PDB Ligand GDM
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