4'-Amino-3'-hydroxydoxorubicin
Basic information
- CAS
106492-47-1- 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](O)[C@H](N)[C@H](C)O1- InChIKey
DPWXJJCAARDEAI-TZSSRYMLSA-N- Molecular formula
- C27H29NO11
- Average molar mass
- 543.5 g/mol
- Monoisotopic mass
- 543.17406074
Overview
exhibits lower cardiotoxicity in the rat and increased cytotoxicity against human cancer and murine transformed cell lines in comparison with doxorubicin
Names & identifiers
- Preferred name
- 4'-Amino-3'-hydroxydoxorubicin
- IUPAC
- (7S,9S)-7-[(2R,4S,5S,6S)-5-amino-4-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- 4'-amino-3'-hydroxydoxorubicin
- Molecular formula
- C27H29NO11
- Molecular weight
- 543.51926
Names & synonyms
106492-47-14'-Amino-3'-hydroxydoxorubicin4'-Amino-3'-hydroxy-doxorubicinRefChem:95918CHEMBL5396875DTXSID10910020(1S,3S)-3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 4-amino-2,4,6-trideoxy-alpha-L-lyxo-hexopyranoside3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 4-amino-2,4,6-trideoxyhexopyranoside5,12-Naphthacenedione, 10-((4-amino-2,4,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
Database identifiers
- CAS
106492-47-1- PubChem CID
- 159309
- DTXSID
DTXSID10910020- ChEMBL
CHEMBL5396875- Nikkaji
- J439.396A
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 206 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 5
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 977
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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