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Nemorubicin

CAT: 0804-HY-15794-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-15794-01Size:5 mg
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Description
Nemorubicin (Methoxymorpholinyl doxorubicin) is a Doxorubicin derivative with potent antitumor activity. Nemorubicin is highly cytotoxic to a variety of tumor cell lines presenting a multidrug-resistant phenotype. Nemorubicin not only intercalate into the duplex DNA, but also result in significant ligands for G-quadruplex DNA segments, stabilizing their structure. Nemorubicin requirs an intact nucleotide excision repair (NER) system to exert its activity[1][2][3][4].
CAS Number
108852-90-0
Product Name Alternative
Methoxymorpholinyl doxorubicin; FCE 23762; PNU 152243
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
G-quadruplex
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Nemorubicin.html
Purity
97.80
Solubility
DMSO : 65 mg/mL (ultrasonic)
Smiles
COC1=C2C(C(C3=C(O)C(C[C@](C(CO)=O)(O)C[C@]4([H])O[C@H]5C[C@H](N6CCO[C@H](OC)C6)[C@H](O)[C@H](C)O5)=C4C(O)=C3C2=O)=O)=CC=C1
Molecular Formula
C32H37NO13
Molecular Weight
643.64
Precautions
H302, H315, H319, H335
References & Citations
[1]Quintieri L, et al. Formation and antitumor activity of PNU-159682, a major metabolite of nemorubicin in human liver microsomes. Clin Cancer Res. 2005 Feb 15;11 (4) :1608-17.|[2]Quintieri L, et al. In vitro hepatic conversion of the anticancer agent nemorubicin to its active metabolite PNU-159682 in mice, rats and dogs: a comparison with human liver microsomes. Biochem Pharmacol. 2008 Sep 15;76 (6) :784-95.|[3]Sabatino MA, et al. Down-regulation of the nucleotide excision repair gene XPG as a new mechanism of drug resistance in human and murine cancer cells. Mol Cancer. 2010 Sep 24;9:259.|[4]Lu H, et al. Potentiation of methoxymorpholinyl doxorubicin antitumor activity by P450 3A4 gene transfer. Cancer Gene Ther. 2009 May;16 (5) :393-404.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Nemorubicin

Nemorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of morpholines and an anthracycline antibiotic. It is functionally related to a doxorubicin.

CAS Number108852-90-0
PubChem CID65907
IUPAC Name(7S,9S)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2R,4S,5S,6S)-5-hydroxy-4-[(2S)-2-methoxymorpholin-4-yl]-6-methyloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Molecular FormulaC32H37NO13
Molecular Weight643.6
XLogP1.7
Topological Polar Surface Area202
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Heavy Atom Count46
Formal Charge0
Complexity1160
SMILES
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N6CCO[C@@H](C6)OC)O
InChI
InChI=1S/C32H37NO13/c1-14-27(36)17(33-7-8-44-22(12-33)43-3)9-21(45-14)46-19-11-32(41,20(35)13-34)10-16-24(19)31(40)26-25(29(16)38)28(37)15-5-4-6-18(42-2)23(15)30(26)39/h4-6,14,17,19,21-22,27,34,36,38,40-41H,7-13H2,1-3H3/t14-,17-,19-,21-,22-,27+,32-/m0/s1
InChIKey
CTMCWCONSULRHO-UHQPFXKFSA-N
Chemical Structure
2D Structure
2D structure of Nemorubicin
CAS: 108852-90-0
CID: 65907
Formula: C32H37NO13
MW: 643.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight643.6
XLogP31.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Exact Mass643.22649023
Monoisotopic Mass643.22649023
Topological Polar Surface Area202 Ų
Heavy Atom Count46
Formal Charge0
Complexity1160
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
T4469-01Nemorubicin
A14363-100Nemorubicin 100mg
A14363-1Nemorubicin 1mg
T71467-01Nemorubicin HCL
A14363-10Nemorubicin 10mg
A14363-50Nemorubicin 50mg
A14363-25Nemorubicin 25mg
A14363-5Nemorubicin 5mg

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