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Entecavir

CAT: 1299-RM-E032200-02Size: 25 mgDry Ice: NoHazardous: No
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CAT#:1299-RM-E032200-02Size:25 mg
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CAS Number
142217-69-4
Molecular Formula
C12H15N5O3
Molecular Weight
277.28
Product Name Synonym
2-amino-9- ((1S,3R,4S) -4-hydroxy-3- (hydroxymethyl) -2-methylenecyclopentyl) -1H-purin-6 (9H) -one

Chemical Information

Entecavir

Entecavir (anhydrous) is guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B. It has a role as an antiviral drug and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is a primary alcohol, a member of 2-aminopurines, an oxopurine and a secondary alcohol.

CAS Number142217-69-4
PubChem CID135398508
IUPAC Name2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
Molecular FormulaC12H15N5O3
Molecular Weight277.28
XLogP-1.3
Topological Polar Surface Area126
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count20
Formal Charge0
Complexity480
SMILES
C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2N=C(NC3=O)N
InChI
InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1
InChIKey
QDGZDCVAUDNJFG-FXQIFTODSA-N
Chemical Structure
2D Structure
2D structure of Entecavir
CAS: 142217-69-4
CID: 135398508
Formula: C12H15N5O3
MW: 277.28
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight277.28
XLogP3-1.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass277.11748936
Monoisotopic Mass277.11748936
Topological Polar Surface Area126 Ų
Heavy Atom Count20
Formal Charge0
Complexity480
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA1816-100Entecavir

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