alvespimycin   Click here for help

GtoPdb Ligand ID: 9828

Synonyms: 17-DMAG
PDB Ligand
Compound class: Synthetic organic
Comment: Alvespimycin is an analogue of the antineoplastic benzoquinone antibiotic geldanamycin, a heat shock protein (HSP) 90 inhibitor. It has been used in trials studying the treatment of solid tumours in various cancers. It has particularly complex stereochemistry with 45 'same-connectivity' relationships in PubChem.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 169.52
Molecular weight 616.35
XLogP 1.03
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1CC(C)CC2=C(NCCN(C)C)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(NCCN(C)C)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/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1
InChI Key KUFRQPKVAWMTJO-LMZWQJSESA-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)-21-[2-(dimethylamino)ethylamino]-6-hydroxy-5,11-dimethoxy-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
Synonyms Click here for help
17-DMAG
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1217507
Reactome Reaction Reactome logo R-HSA-1218824
Other databases
ChEMBL Ligand CHEMBL383824
GtoPdb PubChem SID 354702299
PubChem CID 5288674
RCSB PDB Ligand KOS, KOS
Search Google for chemical match using the InChIKey KUFRQPKVAWMTJO-LMZWQJSESA-N
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Search UniChem for chemicals with the same backbone KUFRQPKVAWMTJO
SynPHARM 84900 (in complex with heat shock protein 90 alpha family class A member 1)