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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31NO10
Molecular Weight 529.5368
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAUNORUBICINOL

SMILES

C[C@@]1([H])[C@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@@]2([H])C[C@@](Cc3c2c(c4c(C(=O)c5cccc(c5C4=O)OC)c3O)O)([C@]([H])(C)O)O)N)O

InChI

InChIKey=HJEZFVLKJYFNQW-PRFXOSGESA-N
InChI=1S/C27H31NO10/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/t10-,11-,14-,16-,17-,22+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H31NO10
Molecular Weight 529.5368
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:56:42 UTC 2021
Edited
by admin
on Sat Jun 26 11:56:42 UTC 2021
Record UNII
YDU8YIP30L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAUNORUBICINOL
Common Name English
LEUKAEMOMYCIN D
Common Name English
13-DIHYDRODAUNOMYCIN
Common Name English
DIHYDRODAUNORUBICIN
Common Name English
DUBORIMYCIN
Common Name English
13-DIHYDRODAUNORUBICIN
Common Name English
5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-((1S)-1-HYDROXYETHYL)-1-METHOXY-, (8S,10S)-
Common Name English
DAUNOMYCINOL
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY, DIHYDRODAUNORUBICIN- [USP]
Common Name English
EPIRUBICIN IMPURITY E
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY E [EP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
Code System Code Type Description
PUBCHEM
443832
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
FDA UNII
YDU8YIP30L
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
DRUG CENTRAL
4719
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
NCI_THESAURUS
C1062
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
MESH
C000847
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
CAS
28008-55-1
Created by admin on Sat Jun 26 11:56:42 UTC 2021 , Edited by admin on Sat Jun 26 11:56:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
MAJOR
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP