2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide

• ChemBase ID: 179834
• Molecular Formular: C22H29N7O5
• Molecular Mass: 471.50956
• Monoisotopic Mass: 471.22301706
• SMILES: n1([C@H]2[C@@H]([C@H](NC(=O)C(Cc3ccc(cc3)OC)N)[C@H](O2)CO)O)c2c(nc1)c(ncn2)N(C)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1NC(=O)C(Cc1ccc(cc1)OC)N)O)n1cnc2c1ncnc2N(C)C
• InChI: InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14?,15-,16-,18-,22-/m1/s1
• InChIKey: RXWNCPJZOCPEPQ-ZRKVXJNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• IUPAC Traditional name: 2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• Synonyms: Achromycin; Stillomycin; Stylomycin; Antibiotic CL 13900; Antibiotic 3123L; Antibiotic P 638; Bacterenomycin; Puromycin

Database IDs

• CAS Number: 53-79-2
• PubChem SID: 164235744
• PubChem CID: 2724365

CALCULATED PROPERTIES

• Acid pKa: 12.349177
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.7910688
• LogD (pH = 7.4): -1.0220252
• Log P: -0.29873976
• Molar Refractivity: 122.9609 cm^3
• Polarizability: 47.873817 Å^3
• Polar Surface Area: 160.88 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Protein synthesis inhibitor

Product Information

• Biological Source: Isol. from Streptomyces alboniger
• Application(s): Antibiotic; Cytostatic

REFERENCES

• Porter, J.N. et al., Antibiot. Chemother. (Washington, D.C.), 1952, 2, 409, (isol)
• Waller, C.W. et al., J.A.C.S., 1953, 75, 2025, (ir, uv, struct)
• Baker, B.R. et al., J.A.C.S., 1954, 76, 4044, (synth)
• Johnson, L.F. et al., J.A.C.S., 1963, 85, 3700, (nmr, struct)
• Eggers, S.H. et al., Tet. Lett., 1966, 3271, (ms, struct)
• Nathans, D., Antibiotics (N.Y.), 1967, 1, 259, (rev)
• Hawtrey, A.O. et al., Tet. Lett., 1967, 1693, (uv)
• Daluge, S. et al., J. Med. Chem., 1972, 15, 171, (pharmacol)
• de Leeuw, H.P.M. et al., Eur. J. Biochem., 1977, 76, 209, (pmr, conformn)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 143
• Narula, S.S. et al., Indian J. Biochem. Biophys., 1985, 22, 1; 1986, 23, 187, (cmr, pmr, conformn)
• Robins, M.J. et al., J.O.C., 2001, 66, 8204-8210, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEI000; POK300