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5'-N-Ethylcarboxamidoadenosine (NECA)

CAT: 1568-C11826-5mgSize: 5 mgDry Ice: NoHazardous: No
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CAT#:1568-C11826-5mgSize:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
35920-39-9
Synonyms
5'- (N-Ethylcarboxamido) adenosine, Adenosine-5'N-ethylcarboxamide, 5'-Ethylcarboxamidoadenosine
Target
Adenosine Receptor
Applications
GPCR & G Protein
Smiles
CCNC (=O) C1OC (C (O) C1O) [N]2C=NC3=C (N) N=CN=C23
Molecular Formula
C12H16N6O4
Additionnal Information
5'-N-Ethylcarboxamidoadenosine (NECA, 5'- (N-Ethylcarboxamido) adenosine, Adenosine-5'N-ethylcarboxamide, 5'-Ethylcarboxamidoadenosine) is a stable, nonselective adenosine receptor agonist. 5'-N-Ethylcarboxamidoadenosine acts via multiple mechanisms including: reducing diabetes-induced oxidative stress, inhibiting gene expression of IL-18, TNF-α and ICAM-1 (intercellular adhesion molecule 1 (CD54) ), and blocking activation of the JNK-MAPK pathway.
Storage Conditions
3 years -20°C powder

Chemical Information

Neca

N-ethyl-5'-carboxamidoadenosine is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group. It has a role as an antineoplastic agent, a vasodilator agent, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine A1 receptor agonist and an adenosine A2A receptor agonist. It is a member of adenosines and a monocarboxylic acid amide. It is functionally related to an adenosine.

CAS Number35920-39-9
PubChem CID448222
IUPAC Name(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
Molecular FormulaC12H16N6O4
Molecular Weight308.29
XLogP-0.7
Topological Polar Surface Area148
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Heavy Atom Count22
Formal Charge0
Complexity426
SMILES
CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI
InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1
InChIKey
JADDQZYHOWSFJD-FLNNQWSLSA-N
Chemical Structure
2D Structure
2D structure of Neca
CAS: 35920-39-9
CID: 448222
Formula: C12H16N6O4
MW: 308.29
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight308.29
XLogP3-0.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass308.12330301
Monoisotopic Mass308.12330301
Topological Polar Surface Area148 Ų
Heavy Atom Count22
Formal Charge0
Complexity426
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
S6347-015'-N-Ethylcarboxamidoadenosine (NECA)
S6347-25mg5´-N-Ethylcarboxamidoadenosine (NECA)
MBS6049190-012-Iodo-5'-ethylcarboxamidoadenosine (2-Iodo-NECA)
I8447-382-Iodo-5’-ethylcarboxamidoadenosine (2-Iodo-NECA)
B1077-97XN6-Benzyl-5’-Ethylcarboxamidoadenosine (N6-Benzyl-NECA)
MBS6052825-01N6-Benzyl-5'-Ethylcarboxamidoadenosine (N6-Benzyl-NECA)
E8604-655’-Ethylcarboxamidoadenosine (NECA, 1- (6-Amino-9H-purin-9-yl) -1-deoxy-N-ethyl-ß-D-ribofuranuronamide)
MBS6070614-015'-Ethylcarboxamidoadenosine (NECA, 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamide)
217157Adenosine Receptor Agonist, NECA ((2S,3S,4R,5R) -5- (6-amino-9H-purin-9-yl) -N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide)
HY-103173-015'-N-Ethylcarboxamidoadenosine

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