methyl (1s,4s)-4-(3-{6-amino-9-[(2R,3R,4S,5S)-5-[(2H5)ethylcarbamoyl]-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}prop-2-yn-1-yl)cyclohexane-1-carboxylate

• ChemBase ID: 160748
• Molecular Formular: C23H30N6O6
• Molecular Mass: 486.5209
• Monoisotopic Mass: 486.22268271
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)C#CC[C@H]1CC[C@H](CC1)C(=O)OC
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(C#CC[C@@H]1CC[C@@H](CC1)C(=O)OC)nc2N
• InChI: InChI=1S/C23H30N6O6/c1-3-25-21(32)18-16(30)17(31)22(35-18)29-11-26-15-19(24)27-14(28-20(15)29)6-4-5-12-7-9-13(10-8-12)23(33)34-2/h11-13,16-18,22,30-31H,3,5,7-10H2,1-2H3,(H,25,32)(H2,24,27,28)/t12-,13+,16-,17+,18-,22+/m0/s1
• InChIKey: FLEVIENZILQUKB-NZORNTTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1s,4s)-4-(3-{6-amino-9-[(2R,3R,4S,5S)-5-[(^2H₅)ethylcarbamoyl]-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}prop-2-yn-1-yl)cyclohexane-1-carboxylate
• IUPAC Traditional name: methyl (1s,4s)-4-(3-{6-amino-9-[(2R,3R,4S,5S)-5-[(^2H₅)ethylcarbamoyl]-3,4-dihydroxyoxolan-2-yl]purin-2-yl}prop-2-yn-1-yl)cyclohexane-1-carboxylate
• Synonyms: 2-[[7-(Trifluoromethyl)-4-quinolinyl]amino]benzoic Acid [4-[3-(Trifluoromethyl)phenyl]-1-piperazinyl-d8]ethyl Ester Hydrochloride; SL 73-033-d8; Stakane-d8 Hydrochloride; Antrafenine-d8 Dihydrochloride

Database IDs

• PubChem SID: 162254883
• PubChem CID: 71313459

CALCULATED PROPERTIES

• Acid pKa: 12.39107
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.8871219
• LogD (pH = 7.4): 0.8871325
• Log P: 0.8871372
• Molar Refractivity: 121.6249 cm^3
• Polarizability: 47.972412 Å^3
• Polar Surface Area: 174.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A697802

Labelled Antrafenone (A697800). A new analgesic.

REFERENCES

• de Julian-Ortiz, J., et al.: J. Med. Chem., 42, 3308 (1999)
• Roy, K., et al.: Bioorg. Med. Chem., 12, 745 (1999)
• Garcia-Garcia, A., et al.: J. Antimicrob. Chemother., 53, 65 (1999)