5(8H)-Naphthacenone, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, monohydrochloride, (8S-cis)-
Basic information
- CAS
67324-99-6- Standard SMILES
COc1cccc2c1C(=N)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl- InChIKey
KVTVLWOKIDKIQL-KOFUDPRISA-N- Molecular formula
- C27H31ClN2O9
- Average molar mass
- 563 g/mol
- Monoisotopic mass
- 562.1718083
Names & identifiers
- Preferred name
- 5(8H)-Naphthacenone, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, monohydrochloride, (8S-cis)-
- IUPAC
- (8S,10S)-8-acetyl-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one;hydrochloride
- English name
- 5-Iminodaunorubicin
- Molecular formula
- C27H31ClN2O9
- Molecular weight
- 563
Names & synonyms
67324-99-65-iminodaunorubicin hydrochloride5(8H)-Naphthacenone, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, monohydrochloride, (8S-cis)-RefChem:9128895-Iminodaunorubicin (hydrochloride)(8S,10S)-8-Acetyl-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one;hydrochlorideNSC 2546815-Iminodaunorubicin HClC27H31ClN2O9orb1745118CHEMBL3230539HY-138645A
Show more names
8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-5(8H)-naphthacenoneMS-30216PD157781CS-0159988G17808(8S,10S)-8-Acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-12-imino-1-methoxy-7,9,10,12-tetrahydrotetracen-5(8H)-one hydrochloride(8S,10S)-8-acetyl-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,8,11-trihydroxy-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one;hydrochloride5(8H)-Naphthacenone, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-|A-L-lyxo-hexopyranosyl)oxy]-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, monohydrochloride, (8S-cis)-
Properties
Computed structural properties
- Topological polar surface area
- 193 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 963
Physicochemical properties
- form
- Solid
- color
- Purple to black
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Applications
Uses5-Iminodaunorubicin hydrochloride is a quinone-modified anthracycline that retains antitumor activity[1]. 5-Iminodaunorubicin hydrochloride produces protein-concealed DNA strand breaks in cancer cells[2].
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