Payload Information

General Information of This Payload
Payload ID
PAY0HZXQT
Name
Idarubicin
Synonyms
IDARUBICIN; 58957-92-9; 4-Demethoxydaunorubicin; 4-Demethoxydaunomycin; Idarubicin Hcl; Idarubicina; Idarubicine; Idamycin; Idarubicine [INN-French]; Idarubicinum [INN-Latin]; Idarubicina [INN-Spanish]; Idarubicinum; Idarubicin [INN:BAN]; IMI-30; 4-Desmethoxydaunorubicin; Daunomycin, 4-demethoxy-; Idarubicin (INN); Zavedos (TN); CCRIS 5083; NSC 256439; UNII-ZRP63D75JW; 4-DMD; ZRP63D75JW; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; CHEBI:42068; NSC-256439; demethoxydaunorubicin; 5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-; Idamycin (TN); IDARUBICIN [INN]; Idarubicin Hcl Pfs; I 1656; Idarubicinhydrochloride; (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; DM5; MLS001401448; NSC256439; (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-; NCGC00093976-03; SMR000466355; SR-01000075934; C26-H27-N-O9; DMDR; IDARUBICIN [MI]; IDARUBICIN [VANDF]; D01XDL; SCHEMBL3750; CHEMBL1117; IDARUBICIN [WHO-DD]; Lopac0_000600; KBioSS_002388; Idarubicin hydrochloride, solid; cid_636362; GTPL7083; 4-DEMETHOXY-DAUNORUBICIN; DTXSID7023142; BDBM58490; XDXDZDZNSLXDNA-TZNDIEGXSA-N; BCPP000207; HMS2089D05; HMS3261H22; Tox21_500600; HY-17381A; AKOS015895563; AC-9384; BCP9000773; CCG-204689; DB01177; LP00600; SDCCGSBI-0050582.P002; NCGC00093976-01; NCGC00093976-02; NCGC00093976-04; NCGC00093976-05; NCGC00093976-18; NCGC00261285-01; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; LS-94015; CS-0007534; EU-0100600; D08062; AB00698511-06; AB00698511-08; AB00698511-09; AB00698511-10; AB00698511_11; EN300-7479233; A832088; A935911; Q1063862; SR-01000075934-1; BRD-K69650333-001-01-1; BRD-K69650333-001-02-9; BRD-K69650333-003-14-0; Idarubicin, United States Pharmacopeia (USP) Reference Standard; (1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE; (1s,3s)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-A-l-lyxo-hexopyranoside; (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride; (7S,9S)-9-Acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione; (7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride; (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride; (7S-cis)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione; 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-; 5,12-NAPHTHACENEDIONE, 9-ACETYL-7-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,9,11-TRIHYDROXY-, (7S,9S)-; 5,12-Naphthacenedione, 9-acetyl-7-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-
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Target(s) DNA topoisomerase 2-alpha (TOP2A)
 Target Info 
Structure
Formula
C26H27NO9
Isosmiles
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
PubChem CID
42890
InChI
InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
InChIKey
XDXDZDZNSLXDNA-TZNDIEGXSA-N
IUPAC Name
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
Pharmaceutical Properties
Molecule Weight
497.5
Polar area
177
Complexity
912
xlogp Value
1.9
Heavy Count
36
Rot Bonds
3
Hbond acc
10
Hbond Donor
5
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Inhibitory Concentration (IC50) 12 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[1]
Half Maximal Inhibitory Concentration (IC50) 12300 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 15 nM
HT-29 cells
Colon adenocarcinoma
CVCL_0320 
[3]
Half Maximal Inhibitory Concentration (IC50) 2 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[4]
Half Maximal Inhibitory Concentration (IC50) 2300 nM
DA-3 cells
Mouse lymphoma
CVCL_5419 
[5]
Half Maximal Inhibitory Concentration (IC50) 3200 nM
ES2 cells
Ewing sarcoma
CVCL_AX39 
[5]
Half Maximal Inhibitory Concentration (IC50) >33000 nM
Vero C1008 cells
Normal
CVCL_0574 
[6]
Half Maximal Inhibitory Concentration (IC50) >33000 nM
Vero C1008 cells
Normal
CVCL_0574 
[6]
Half Maximal Inhibitory Concentration (IC50) 4500 nM
SK-OV-3 cells (FZD7 overexpression)
Ovarian serous cystadenocarcinoma
CVCL_0532 
[5]
Half Maximal Inhibitory Concentration (IC50) 6620 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[2]
Half Maximal Inhibitory Concentration (IC50) 7300 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[5]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Curcumin induces high levels of topoisomerase I- and II-DNA complexes in K562 leukemia cells. J Nat Prod. 2007 Dec;70(12):1884-8. doi: 10.1021/np070332i. Epub 2007 Dec 13.
Ref 2 Liver-stage malaria parasites vulnerable to diverse chemical scaffolds. Proc Natl Acad Sci U S A. 2012 May 29;109(22):8511-6. doi: 10.1073/pnas.1118370109. Epub 2012 May 14.
Ref 3 Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site. Bioorg Med Chem. 2007 Jul 1;15(13):4456-69. doi: 10.1016/j.bmc.2007.04.028. Epub 2007 Apr 22.
Ref 4 Solution structure of iron(III)-anthracycline complexes. J Med Chem. 1999 Jul 29;42(15):2844-51. doi: 10.1021/jm981057n.
Ref 5 The structure of anthracycline derivatives determines their subcellular localization and cytotoxic activity. ACS Med Chem Lett. 2013 Feb 4;4(3):323-8. doi: 10.1021/ml3002852. eCollection 2013 Mar 14.
Ref 6 Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort.

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