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EHNA (hydrochloride)

CAT: 0804-HY-103160A-01Size: 2 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-103160A-01Size:2 mg
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Description
EHNA hydrochloride is a potent and selective dual inhibitor of cyclic nucleotide phosphodiesterase 2 (PDE2) (IC50=4 μM) and adenosine deaminase (ADA) . EHNA hydrochloride exerts a concentration inhibition of the cGMP-stimulated PDE II (cGs-PDE) (IC50:0.8 μM (human), 2 μM (porcine myocardium) ), but has smaller inhibitory effect on the unstimulated PDE2 activity. EHNA hydrochloride play roles in mediating diverse pharmacological responses, including antiviral, antitumour and antiarrhythmic effects[1][2].
CAS Number
58337-38-5
UNSPSC
12352005
Target
Adenosine Deaminase; Influenza Virus; Phosphodiesterase (PDE)
Type
Reference compound
Related Pathways
Anti-infection; Metabolic Enzyme/Protease
Applications
COVID-19-anti-virus
Field of Research
Cancer; Infection; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/ehna-hydrochloride.html
Purity
99.67
Solubility
DMSO : 83.33 mg/mL (ultrasonic; warming; heat to 60°C) |H2O : 100 mg/mL (ultrasonic)
Smiles
CCCCCC[C@@](N1C2=C(C(N)=NC=N2)N=C1)([H])[C@H](O)C.Cl
Molecular Formula
C14H24ClN5O
Molecular Weight
313.83
References & Citations
[1]Podzuweit T, et al. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9- (2-hydroxy-3-nonyl) adenine.Cell Signal. 1995 Sep;7 (7) :733-8.|[2]Michie AM, et al. Rapid regulation of PDE-2 and PDE-4 cyclic AMP phosphodiesterase activity following ligation of the T cell antigen receptor on thymocytes: analysis using the selective inhibitors erythro-9- (2-hydroxy-3-nonyl) -adenine (EHNA) and rolipram.Cell Signal. 1996 Feb;8 (2) :97-110.|[3]Blázquez-Bermejo C, et al. Increased dNTP pools rescue mtDNA depletion in human POLG-deficient fibroblasts. FASEB J. 2019 Jun;33 (6) :7168-7179.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
PDE2

Chemical Information

Erythro-9-(2-hydroxy-3-nonyl)adenine monohydrochloride

(2R,3S)-EHNA hydrochloride is a hydrochloride salt obtained by reaction of (2R,3S)-EHNA with one equivalent of hydrochloric acid. Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase. It has a role as an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor and an EC 3.5.4.4 (adenosine deaminase) inhibitor. It contains a (2R,3S)-EHNA(1+).

CAS Number58337-38-5
PubChem CID11957547
IUPAC Name(2R,3S)-3-(6-aminopurin-9-yl)nonan-2-ol;hydrochloride
Molecular FormulaC14H24ClN5O
Molecular Weight313.82
Topological Polar Surface Area89.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Heavy Atom Count21
Formal Charge0
Complexity291
SMILES
CCCCCC[C@@H]([C@@H](C)O)N1C=NC2=C(N=CN=C21)N.Cl
InChI
InChI=1S/C14H23N5O.ClH/c1-3-4-5-6-7-11(10(2)20)19-9-18-12-13(15)16-8-17-14(12)19;/h8-11,20H,3-7H2,1-2H3,(H2,15,16,17);1H/t10-,11+;/m1./s1
InChIKey
VVDXNJRUNJMYOZ-DHXVBOOMSA-N
Chemical Structure
2D Structure
2D structure of Erythro-9-(2-hydroxy-3-nonyl)adenine monohydrochloride
CAS: 58337-38-5
CID: 11957547
Formula: C14H24ClN5O
MW: 313.82
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight313.82
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Exact Mass313.1669381
Monoisotopic Mass313.1669381
Topological Polar Surface Area89.9 Ų
Heavy Atom Count21
Formal Charge0
Complexity291
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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