U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31NO10.ClH
Molecular Weight 565.997
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Daunorubicinol hydrochloride

SMILES

Cl.[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)[C@H](C)O

InChI

InChIKey=LQLMJJJLWJUAMM-VSTLEVLBSA-N
InChI=1S/C27H31NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,11-,14-,16-,17-,22+,27-;/m0./s1

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Two allelic variants of aldo-keto reductase 1A1 exhibit reduced in vitro metabolism of daunorubicin.
2008 May
Cancer biomarker AKR1B10 and carbonyl metabolism.
2009 Mar 16
Daunorubicin metabolism in leukemic cells isolated from patients with acute myeloid leukemia.
2010 Dec
AKR1B10 induces cell resistance to daunorubicin and idarubicin by reducing C13 ketonic group.
2011 Aug 15
Curcumin is a tight-binding inhibitor of the most efficient human daunorubicin reductase--Carbonyl reductase 1.
2015 Jun 5
Patents
Name Type Language
Daunorubicinol hydrochloride
Common Name English
L-lyxo-Hexopyranoside, 1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-, hydrochloride, (1S,3S)- α-
Systematic Name English
13-Dihydrodaunorubicin hydrochloride
Systematic Name English
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-[(1S)-1-hydroxyethyl]-1-methoxy-, hydrochloride (1:1), (8S,10S)-
Systematic Name English
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-, hydrochloride, [8S-[8α,8(R*),10α]]-
Systematic Name English
Dihydrodaunomycin hydrochloride
Common Name English
Code System Code Type Description
CAS
28008-53-9
Created by admin on Sat Dec 16 19:50:13 GMT 2023 , Edited by admin on Sat Dec 16 19:50:13 GMT 2023
PRIMARY
FDA UNII
2JQ6974KH2
Created by admin on Sat Dec 16 19:50:13 GMT 2023 , Edited by admin on Sat Dec 16 19:50:13 GMT 2023
PRIMARY
PUBCHEM
168012705
Created by admin on Sat Dec 16 19:50:13 GMT 2023 , Edited by admin on Sat Dec 16 19:50:13 GMT 2023
PRIMARY