Annamycin

CAT: 0931-T68326-02Size: 25 mgDry Ice: NoHazardous: No

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CAT#:0931-T68326-02Size:25 mg

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CAS Number

92689-49-1

Target

Others, Antibiotic

Related Pathways

Others, Microbiology/Virology

Bioactivity

Annamycin is a semi-synthetic doxorubicin analogue annamycin with antineoplastic activity. Annamycin intercalates into DNA and inhibits topoisomerase II, resulting in the inhibition of DNA replication and repair and RNA and protein synthesis. This agent circumvents multidrug-resistance (MDR) transporters, including P-glycoprotein (P-gp) .

Smiles

OC=1C2=C([C@@H](O[C@H]3[C@H](I)[C@H](O)[C@@H](O)[C@H](C)O3)C[C@@](C(CO)=O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=O)=CC=CC5

Molecular Formula

C26H25IO11

Molecular Weight

640.37

Shipping Conditions

Ice Packs

Storage Temperature

-20°C

Chemical Information

Annamycin

Naxtarubicin is a lipophilic, anthracycline antineoplastic antibiotic.Naxtarubicin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and repair as well as inhibiting RNA and protein synthesis. This agent appears to not be a substrate for the p-glycoprotein associated multidrug-resistance (MDR) transporter; therefore, overcoming the resistance pattern seen with other anthracycline compounds.

CAS Number	92689-49-1
PubChem CID	115212
IUPAC Name	(7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
Molecular Formula	C26H25IO11
Molecular Weight	640.4
XLogP	2.2
Topological Polar Surface Area	191
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Heavy Atom Count	38
Formal Charge	0
Complexity	961

SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O

InChI

InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1

InChIKey

CIDNKDMVSINJCG-GKXONYSUSA-N

Chemical Structure

2D Structure

CAS: 92689-49-1

CID: 115212

Formula: C26H25IO11

MW: 640.4

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	640.4
XLogP3	2.2
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	640.04416
Monoisotopic Mass	640.04416
Topological Polar Surface Area	191 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	961
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
GTR19211550-01	Annamycin
AR-A06645-01	Annamycin-d3

Annamycin

Chemical Information

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