Aclacinomycin N
Basic information
- CAS
64474-88-0- Standard SMILES
CC[C@@]1(O)C[C@H](O[C@H]2C[C@H](N(C)C)[C@H](O[C@H]3C[C@H](O)[C@H](O[C@H]4CC[C@H](O)[C@H](C)O4)[C@H](C)O3)[C@H](C)O2)c2c(cc3c(c2O)C(=O)c2c(O)cccc2C3=O)[C@H]1C(=O)OC- InChIKey
CPUWOKRFRYWIHK-BPPBZOKFSA-N- Molecular formula
- C42H55NO15
- Average molar mass
- 813.9 g/mol
- Monoisotopic mass
- 813.35717005
Overview
Aclacinomycin N is an anthracycline antibiotic that is aclacinomycin A in which the keto group on the trisaccharide fragment has been reduced in a stereospecific manner to the corresponding alcohol. It has a role as a metabolite, an antimicrobial agent and an antineoplastic agent. It is a methyl ester, a polyketide, a tertiary alcohol, 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 N(1+). It is a tautomer of an aclacinomycin N zwitterion.
Names & identifiers
- Preferred name
- Aclacinomycin N
- IUPAC
- methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
Names & synonyms
aclacinomycin NCHEBI:75091RefChem:915043MA 144 N1Antibiotic MA 144N164474-88-0methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylateMA 144N1SCHEMBL30906985DTXSID902147351-Naphthacenecarboxylic acid, 1,2,3,4,6,11-hexahydro-6,11-dioxo-2-ethyl-2,5,7-trihydroxy-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2S-(2-alpha,5-beta,6-beta))tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1-alpha,2-beta,4-beta))-C18637
Show more names
Q27145119Methyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-O-{2,6-dideoxy-4-O-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-alpha-L-lyxo-hexopyranosyl}-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylatemethyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-O-{2,6-dideoxy-4-O-[(2S,5S,6S)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]-alpha-L-lyxo-hexopyranosyl}-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 220 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 10
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 1,480
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
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Compound notes
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