Alvespimycin
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-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
Molecular Identity
Alvespimycin
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-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
PubChem CID: 5288674
Alvespimycin is a 19-membered macrocyle that is geldanamycin in which the methoxy group attached to the benzoquinone moiety has been replaced by a 2-(N,N-dimethylamino)ethylamino group. It has a role as a Hsp90 inhibitor. It is a member of 1,4-benzoquinones, an ansamycin, a carbamate ester, a secondary amino compound and a tertiary amino compound. It is functionally related to a geldanamycin.
2D Structure
Properties
C32H48N4O8
Molecular Formula
616.70
Molecular Weight
g/mol
616.3472
Exact Mass
Da
2
XLogP
Drug-like (Lipinski: < 5)
170
TPSA
May have limited oral absorption
4
H-Bond Donors
10
H-Bond Acceptors
1230
Complexity
SMILES
Canonical SMILES
SMILES: CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCCN(C)C)C)OC)OC(=O)N)C)C)O)OCIsomeric SMILES
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)NCCN(C)C)/C)OC)OC(=O)N)\C)C)O)OCSynonyms(20)
alvespimycin467214-20-617-DMAGAlvespimycin [INN]alvespimicinaalvespimycineUNII-001L2FE0M3[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate17-dimethylaminoethylamino-17-demethoxygeldanamycinCHEBI:6532417-(dimethylaminoethylamino)-17-demethoxygeldanamycinNSC707545NSC-707545ALVESPIMYCIN [WHO-DD](4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-13-hydroxy-8,14-dimethoxy-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
Data from PubChem (NCBI)
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