Molecular Identity
Doxorubicin
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
PubChem CID: 31703
Doxorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, an aminoglycoside, an anthracycline, an anthracycline antibiotic and a member of tetracenequinones. It has a role as an Escherichia coli metabolite. It is functionally related to an Adriamycinone. It is a conjugate base of a doxorubicin(1+). It derives from a hydride of a tetracene.
2D Structure
Properties
C27H29NO11
Molecular Formula
543.50
Molecular Weight
g/mol
543.1741
Exact Mass
Da
1.3
XLogP
Drug-like (Lipinski: < 5)
206
TPSA
May have limited oral absorption
6
H-Bond Donors
12
H-Bond Acceptors
977
Complexity
SMILES
Canonical SMILES
SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OIsomeric SMILES
SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OSynonyms(20)
doxorubicinAdriamycin23214-92-8AdriablastinDoxorubicine14-HydroxydaunomycinDoxorubicinumDoxorubicina14-HydroxydaunorubicineNDC 38242-874NSC 123127(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dioneNSC-123127NSC-75915580168379AG
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Doxorubicin
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