2-{[(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl]oxy}ethyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 171409
• Molecular Formular: C58H95N2O17P
• Molecular Mass: 1123.351861
• Monoisotopic Mass: 1122.63683622
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@@H](C[C@H]1C[C@H]([C@@H](CC1)OCCOP(=O)(OCC[N+](C)(C)C)[O-])OC)C)CC(=O)[C@@H](/C=C(/[C@H]([C@H](C(=O)[C@@H](C[C@@H](/C=C/C=C/C=C(/[C@@H](C[C@@H]1CC[C@H]([C@](C(=O)C2=O)(O1)O)C)OC)\C)C)C)OC)O)\C)C
• Canonical SMILES: CO[C@@H]1C[C@@H](CC[C@H]1OCCOP(=O)(OCC[N+](C)(C)C)[O-])C[C@H]([C@@H]1CC(=O)[C@H](C)/C=C(\C)/[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C(/[C@@H](C[C@H]2O[C@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)(O)[C@H](C)CC2)OC)\C)C
• InChI: InChI=1S/C58H95N2O17P/c1-37-19-15-14-16-20-38(2)49(70-11)35-45-24-22-43(7)58(67,77-45)55(64)56(65)59-26-18-17-21-46(59)57(66)76-50(36-47(61)39(3)32-42(6)53(63)54(72-13)52(62)41(5)31-37)40(4)33-44-23-25-48(51(34-44)71-12)73-29-30-75-78(68,69)74-28-27-60(8,9)10/h14-16,19-20,32,37,39-41,43-46,48-51,53-54,63,67H,17-18,21-31,33-36H2,1-13H3/b16-14+,19-15+,38-20+,42-32+/t37-,39-,40-,41-,43-,44+,45?,46+,48-,49-,50+,51-,53-,54+,58-/m1/s1
• InChIKey: XBFREHBEJFQNTO-LVHPSTRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl]oxy}ethyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: 2-{[(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl]oxy}ethyl 2-(trimethylammonio)ethyl phosphate
• Synonyms: ATG 181; 42-O-[2-[[Hydroxy[2-(trimethylammonio)ethoxy]phosphinyl]oxy]ethyl] Rapamycin Inner Salt >75%

Database IDs

• CAS Number: 1062645-51-5
• PubChem SID: 164227319
• PubChem CID: 71749395

CALCULATED PROPERTIES

• Acid pKa: 1.8587986
• H Acceptors: 14
• H Donor: 2
• LogD (pH = 5.5): 5.538055
• LogD (pH = 7.4): 5.5369835
• Log P: 3.514567
• Molar Refractivity: 309.8729 cm^3
• Polarizability: 117.16383 Å^3
• Polar Surface Area: 243.02 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 135-140°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H972100

A phosphocholine ester metabolite of the immunosuppressant macrolide SDZ RAD (also known as Everolimus E945400) which is an analog of the parent drug Rapamycin (R124000).

REFERENCES

• Zollinger, M. et al.: Drug. Metab. Disp., 36, 1457 (2008)
• Kovarik, J. M., et al.: Clin. Pharmacol. Ther., 69, 48 (2008)