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

• ChemBase ID: 102200
• Molecular Formular: C22H29N7O5
• Molecular Mass: 471.50956
• Monoisotopic Mass: 471.22301706
• SMILES: COc1ccc(CC(N)C(=O)NC2C(O)C(OC2CO)n2cnc3c2ncnc3N(C)C)cc1
• Canonical SMILES: OCC1OC(C(C1NC(=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)
• InChIKey: RXWNCPJZOCPEPQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-{5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl}-3-(4-methoxyphenyl)propanamide
• IUPAC Traditional name: puromycin
• Synonyms: Stylomycin; 6-dimethylamino-9-(3'-deoxy-3'-(p-methoxy-L-phenylalanyamino)-B-D-ribofuranosyl)-purine; PUROMYCIN DIHYDROCHLORIDE

Database IDs

• CAS Number: 58-58-2
• EC Number: 200-387-8
• PubChem SID: 162089977
• PubChem CID: 4984

CALCULATED PROPERTIES

• Acid pKa: 12.349177
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.8206933
• LogD (pH = 7.4): -1.0225005
• 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

Safety Information

• Storage Condition: 0°C
• RTECS: AU7355000

DETAILS

MP Biomedicals - 02100552

Dihydrochloride Crystalline Antimicrobial Causes premature chain termination in protein synthesis, and is an inhibitor of aminopeptidase and enkephalinase.

REFERENCES

• Reboud, A.M., et al., Biochemistry, 20 : 5281 (1981).
• Pekarek, J., et al., Immunology, 31: 773 (1976).