13-Dihydrodaunorubicin
Basic information
- CAS
28008-55-1- Standard SMILES
COc1cccc2c1C(=O)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- InChIKey
HJEZFVLKJYFNQW-FKKRWUELSA-N- Molecular formula
- C27H31NO10
- Average molar mass
- 529.5 g/mol
- Monoisotopic mass
- 529.19479619
Overview
13-dihydrodaunorubicin is an aminoglycoside antibiotic that is (1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene having a 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl residue attached at position 1 via a glycosidic linkage. It is an aminoglycoside antibiotic, a member of p-quinones, a deoxy hexoside, an anthracycline and a monosaccharide derivative. It is a conjugate base of a 13-dihydrodaunorubicin(1+). It derives from a hydride of a tetracene.
Names & identifiers
- Preferred name
- 13-Dihydrodaunorubicin
- IUPAC
- (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- DAUNOMYCINOL
- Molecular formula
- C27H31NO10
- Molecular weight
- 529.54
Names & synonyms
13-DihydrodaunorubicinCHEBI:31059(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione(7S,9S)-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dioneRefChem:1057466Daunorubicin EP Impurity BDuborimycin(1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosideEpirubicin Hydrochloride EP Impurity ESCHEMBL1136412CHEMBL3544589DTXSID20950699
Show more names
daunorubicinol13-dihydrodaunomycinC12430DAUNOMYCINOLleukaemomycinddihydrodaunomycinantibiotic20-798rpDAUNOMYCINOL USP/EP/BP
LMPK13050004V73O8640X8ID183436Q27114110DAUNORUBICIN HYDROCHLORIDE IMPURITY B [EP IMPURITY](8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-8-((1RS)-1-HYDROXYETHYL)-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE(8S,10S)-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-8-((1rs)-1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 189 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 918
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Anthracyclinones [PK1305]
Physicochemical properties
- Melting point
- 173 °C · >173°C (dec.)
- Boiling point
- 609.35 °C · 609.35°C (rough estimate)
- Density
- 1.3345 · 1.3345 (rough estimate)
- refractive index
- 1.64 · 1.6400 (estimate)
- storage temp.
- -20 °C, · -20°C, Hygroscopic
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 7.54 · 7.54±0.60(Predicted)
- form
- Solid
- color
- Red to Dark Red
- Stability
- Hygroscopic
- FDA UNII
- 8 YIP30L · YDU8YIP30L
- NCI Drug Dictionary
- duborimycin
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS07
- Hazard statements
- H332-H302-H350-H360-H312-H340
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Applications
UsesDaunorubicinol is a metabolite of Daunorubicin (D194500, HCl salt).
Additional notes
DefinitionChEBI: An aminoglycoside antibiotic that is (1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene having a 3-amino-2,3,6-trideoxy-alpha-L-lyxo /stereo>-hexopyranosyl residue attached at position 1 via a glycosidic linkage.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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