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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31NO11
Molecular Weight 545.5351
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXORUBICINOL

SMILES

COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)[C@@H](O)CO)C(O)=C3C(=O)C2=CC=C1

InChI

InChIKey=NKZRZOVSJNSBFR-FEMMEMONSA-N
InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H31NO11
Molecular Weight 545.5351
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism of doxorubicin to the cardiotoxic metabolite doxorubicinol is increased in a mouse model of chronic glutathione deficiency: A potential role for carbonyl reductase 3.
2015-06-05
Identification of carbonyl reductase 1 as a resveratrol-binding protein by affinity chromatography using 4'-amino-3,5-dihydroxy-trans-stilbene.
2013
Two allelic variants of aldo-keto reductase 1A1 exhibit reduced in vitro metabolism of daunorubicin.
2008-05
Doxorubicin irreversibly inactivates iron regulatory proteins 1 and 2 in cardiomyocytes: evidence for distinct metabolic pathways and implications for iron-mediated cardiotoxicity of antitumor therapy.
2001-12-01
The role of biotransformation in anthracycline-induced cardiotoxicity in mice.
1993-09
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:12:55 GMT 2025
Edited
by admin
on Mon Mar 31 22:12:55 GMT 2025
Record UNII
HUH05KI4CF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RP-27706
Preferred Name English
DOXORUBICINOL
Common Name English
13-DIHYDRODOXORUBICIN
Common Name English
ANTIBIOTIC 27706RP
Common Name English
ADRIAMYCINOL
Common Name English
Code System Code Type Description
FDA UNII
HUH05KI4CF
Created by admin on Mon Mar 31 22:12:55 GMT 2025 , Edited by admin on Mon Mar 31 22:12:55 GMT 2025
PRIMARY
CHEBI
133817
Created by admin on Mon Mar 31 22:12:55 GMT 2025 , Edited by admin on Mon Mar 31 22:12:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID70920620
Created by admin on Mon Mar 31 22:12:55 GMT 2025 , Edited by admin on Mon Mar 31 22:12:55 GMT 2025
PRIMARY
CAS
54193-28-1
Created by admin on Mon Mar 31 22:12:55 GMT 2025 , Edited by admin on Mon Mar 31 22:12:55 GMT 2025
PRIMARY
PUBCHEM
83970
Created by admin on Mon Mar 31 22:12:55 GMT 2025 , Edited by admin on Mon Mar 31 22:12:55 GMT 2025
PRIMARY
Related Record Type Details
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