Geldanamycin
[(4E,6Z,8S,9S,10E,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
Molecular Identity
Geldanamycin
[(4E,6Z,8S,9S,10E,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
PubChem CID: 5288382
Geldanamycin is an ansamycin consisting of a 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It shows antimicrobial activity against many Gram-positive and some Gram-negative bacteria. It has a role as an antiviral agent, an antimicrobial agent, an antineoplastic agent, a Hsp90 inhibitor and a cysteine protease inhibitor. It is a member of 1,4-benzoquinones, an ansamycin, a carbamate ester and an organic heterobicyclic compound.
2D Structure
Properties
C29H40N2O9
Molecular Formula
560.60
Molecular Weight
g/mol
560.2734
Exact Mass
Da
2
XLogP
Drug-like (Lipinski: < 5)
163
TPSA
May have limited oral absorption
3
H-Bond Donors
9
H-Bond Acceptors
1150
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)OC)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)OC)/C)OC)OC(=O)N)\C)C)O)OCSynonyms(20)
geldanamycin30562-34-6geldanomycinZ3K3VJ16KUNSC-122750CHEBI:5292DTXSID7042691[(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] carbamateAntibiotic U 29135[(4E,6Z,8S,9S,10E,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] carbamateAntibiotic (U-29,135)NSC212518((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((4E,6Z,8S,9S,10E,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) carbamateRefChem:142823
Data from PubChem (NCBI)
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