Aclarubicin
methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
Molecular Identity
Aclarubicin
methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
PubChem CID: 451415
Aclacinomycin A is an anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity. It has a role as an antimicrobial agent, an antineoplastic agent, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an apoptosis inducer and a bacterial metabolite. It is a methyl ester, a polyketide, a member of phenols, an aminoglycoside, an anthracycline, a member of tetracenequinones and a trisaccharide derivative. It is functionally related to an aklavinone. It is a conjugate base of an aclacinomycin A(1+). It is a tautomer of an aclacinomycin A zwitterion.
2D Structure
Properties
C42H53NO15
Molecular Formula
811.90
Molecular Weight
g/mol
811.3415
Exact Mass
Da
3.8
XLogP
Drug-like (Lipinski: < 5)
217
TPSA
May have limited oral absorption
4
H-Bond Donors
16
H-Bond Acceptors
1530
Complexity
SMILES
Canonical SMILES
SMILES: CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)OIsomeric SMILES
SMILES: CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@@H]([C@@H](O6)C)O[C@H]7CCC(=O)[C@@H](O7)C)O)N(C)C)OSynonyms(20)
aclarubicinAclacinomycin A57576-44-0AclarubicineAclarubicinumaclarubicinaNSC-208734MA 144-A174KXF8I502CHEBI:74619methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylateNSC 208734NSC2087341-Naphthacenecarboxylic acid,(2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-Lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1alpha,2beta,4beta))-Antibiotic MA144-A1
Data from PubChem (NCBI)
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