5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-
Basic information
- CAS
81382-05-0- Standard SMILES
C[C@@H]1O[C@@H](O[C@H]2C[C@](O)(C(=O)CO)Cc3cc4c(c(O)c32)C(=O)c2c(O)cccc2C4=O)C[C@H](N)[C@@H]1O- InChIKey
ROILTUODAPUWLG-NRFWZUBKSA-N- Molecular formula
- C26H27NO10
- Average molar mass
- 513.5 g/mol
- Monoisotopic mass
- 513.16349606
Overview
1-O-demethyl-6-deoxydoxorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, an aminoglycoside and an anthracycline. It is functionally related to a doxorubicin.
Names & identifiers
- Preferred name
- 5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-
- IUPAC
- (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- 5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-
- Molecular formula
- C26H27NO10
- Molecular weight
- 513.49328
Names & synonyms
RefChem:5275975,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-1-O-DEMETHYL-6-DEOXYDOXORUBICIN(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione(1S,3S)-3,10,12-trihydroxy-3-(hydroxyacetyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosideCHEBI:41919Q271204394-O-demethyl-11-deoxydoxorubicin
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 197 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 929
Physicochemical properties
- Boiling point
- 772.9 · 772.9±60.0 °C(Predicted)
- Density
- 1.62 · 1.62±0.1 g/cm3(Predicted)
- pka
- 6.44 · 6.44±0.60(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-(hydroxyacetyl)-, (8S,10S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Chemistry & industry
Applications
Uses4-O-Demethyl-11-deoxydoxorubicin is an anthracycline antibiotic with antibacterial and antitumor activities. 4-O-Demethyl-11-deoxydoxorubicin is cytotoxic to Hela cells[1].
Additional notes
DefinitionChEBI: 1-O-demethyl-6-deoxydoxorubicin is an aminoglycoside, an anthracycline, a deoxy hexoside, a member of p-quinones, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It is functionally related to a doxorubicin.
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