(2R,3R)-4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid

• ChemBase ID: 168164
• Molecular Formular: C9H11N5O4
• Molecular Mass: 253.21474
• Monoisotopic Mass: 253.08110386
• SMILES: n1cnc2c(c1N)ncn2C[C@H]([C@@H](O)C(=O)O)O
• Canonical SMILES: O[C@@H]([C@H](C(=O)O)O)Cn1cnc2c1ncnc2N
• InChI: InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1
• InChIKey: LIEMBEWXEZJEEZ-INEUFUBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid
• IUPAC Traditional name: (2R,3R)-4-(6-aminopurin-9-yl)-2,3-dihydroxybutanoic acid
• Synonyms: (αR,βR)-6-Amino-α,β-dihydroxy-9H-purine-9-butanoic Acid; 4-(6-Amino-9H-purin-9-yl)-4-deoxy-D-erythronic Acid; 4-(6-Aminopurin-9-yl)-4-deoxy-D-erythronic Acid; Lentinacin; Lentysine; 4-(9-Adenyl)-D-erythro-2,3-dihydroxybutyric Acid; D-Eritadenine; Eritadenine

Database IDs

• CAS Number: 23918-98-1
• PubChem SID: 162262296
• PubChem CID: 159961

CALCULATED PROPERTIES

• Acid pKa: 3.261468
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.1504397
• LogD (pH = 7.4): -5.336264
• Log P: -3.7004676
• Molar Refractivity: 59.5807 cm^3
• Polarizability: 22.665798 Å^3
• Polar Surface Area: 147.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Sparingly soluble in DMSO and Water
• Apperance: Pale Yellow Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E600100

Hypocholesterolemic isolated from shiitake mushrooms, effecting phospholipid and linoleic acid metabolisms. Specifically, Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.

REFERENCES

• Fukada, S., et al.: J. Nut., 136, 2797 (2006)
• Vilar, S., et al.: J. Med. Chem., 49, 1118 (2006)
• Yamada, T., et al.: Biochem. Pharmacol., 73, 981 (2006)
• Enman, J., et al.; J. Agric. Food Chem., 56, 2609 (2006)