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(R) -Amrubicin

CAT: 0804-HY-B0067BSize: 1 EachDry Ice: NoHazardous: No
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Description
(R) -Amrubicin ((R) -SM-5887) is an anthracycline that effectively treats lung cancer by intercalating into DNA and inhibiting topoisomerase II activity, which consequently hampers DNA replication as well as RNA and protein synthesis, leading to cell growth inhibition and apoptosis. This compound exhibits superior anti-tumor efficacy compared to traditional anthracycline drugs while lacking the cumulative cardiac toxicity typically associated with this drug class.
CAS Number
92395-36-3
Product Name Alternative
(R) -SM-5887
UNSPSC
12352005
Target
Topoisomerase
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/r-amrubicin.html
Smiles
CC([C@@](C1)(N)C[C@H](O[C@H]2OC[C@@H](O)[C@@H](O)C2)C(C1=C3O)=C(O)C4=C3C(C5=CC=CC=C5C4=O)=O)=O
Molecular Formula
C25H25NO9
Molecular Weight
483.47
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

9-acetyl-9-amino-7-(4,5-dihydroxyoxan-2-yl)oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
CAS Number92395-36-3
PubChem CID21983484
IUPAC Name9-acetyl-9-amino-7-(4,5-dihydroxyoxan-2-yl)oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Molecular FormulaC25H26ClNO9
Molecular Weight519.9
Topological Polar Surface Area177
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Heavy Atom Count36
Formal Charge0
Complexity881
SMILES
CC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)OC5CC(C(CO5)O)O)N.Cl
InChI
InChI=1S/C25H25NO9.ClH/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31;/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3;1H
InChIKey
BHMLHEQFWVQAJS-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 9-acetyl-9-amino-7-(4,5-dihydroxyoxan-2-yl)oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
CAS: 92395-36-3
CID: 21983484
Formula: C25H26ClNO9
MW: 519.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight519.9
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Exact Mass519.1296091
Monoisotopic Mass519.1296091
Topological Polar Surface Area177 Ų
Heavy Atom Count36
Formal Charge0
Complexity881
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count5
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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