Iododoxorubicin
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Basic information
- CAS
83997-75-5- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](I)[C@H](C)O1- InChIKey
PDQGEKGUTOTUNV-TZSSRYMLSA-N- Molecular formula
- C27H28INO10
- Average molar mass
- 653.4 g/mol
- Monoisotopic mass
- 653.07579
Overview
4'-deoxy-4'-iododoxorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone and an organoiodine compound. It is functionally related to a doxorubicin. It is a conjugate base of a 4'-deoxy-4'-iododoxorubicinium.
Names & identifiers
- Preferred name
- Iododoxorubicin
- IUPAC
- (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- 5,12-Naphthacenedione, 10-(2R,4S,5S,6S)-4-aminotetrahydro-5-iodo-6-methyl-2H-pyran-2-yloxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
- Molecular formula
- C27H28INO10
- Molecular weight
- 653.42
Names & synonyms
Iododoxorubicin4'-Iodo-4'-deoxydoxorubicin4'-Deoxy-4'-iododoxorubicin83997-75-54'-deoxy-4'-IDX65JH75I9JXFCE-21954CHEBI:47897(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-iodo-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione5,12-Naphthacenedione, 10-(((2R,4S,5S,6S)-4-aminotetrahydro-5-iodo-6-methyl-2H-pyran-2-yl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-4'-iododoxorubicin4'-iododeoxyrubicin
Show more names
5,12-Naphthacenedione, 10-(2R,4S,5S,6S)-4-aminotetrahydro-5-iodo-6-methyl-2H-pyran-2-yloxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-5,12-Naphthacenedione, 10-[[(2R,4S,5S,6S)-4-aminotetrahydro-5-iodo-6-methyl-2H-pyran-2-yl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-iodo-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dioneRefChem:95964NSC-378901FCE 21954Iodo-DoxPDQGEKGUTOTUNV-TZSSRYMLSA-NDTXSID301004258IDX
Properties
Computed structural propertiesFilling in
- XLogP
- 2.9
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 5
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 982
Experimental & physicochemical properties
LogP1.53
Physicochemical properties
- Boiling point
- 813.2 · 813.2±65.0 °C(Predicted)
- Density
- 1.81 · 1.81±0.1 g/cm3(Predicted)
- pka
- 7.35 · 7.35±0.60(Predicted)
- FDA UNII
- 65 JH75I9JX · 65JH75I9JX
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-(2R,4S,5S,6S)-4-aminotetrahydro-5-iodo-6-methyl-2H-pyran-2-yloxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (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
Additional notes
DefinitionChEBI: 4'-deoxy-4'-iododoxorubicin is an organoiodine compound, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It is functionally related to a doxorubicin. It is a conjugate acid of a 4'-deoxy-4'-iododoxorubicinium.
Related reactions
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Compound notes
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