(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 dimethylphosphinate

• ChemBase ID: 177535
• Molecular Formular: C53H84NO14P
• Molecular Mass: 990.206121
• Monoisotopic Mass: 989.562943
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@@H](C[C@H]1C[C@H]([C@@H](CC1)OP(=O)(C)C)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]1OP(=O)(C)C)C[C@H]([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H](CC[C@H]2C)C[C@@H](OC)/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C1)C)/C)O)OC)C)C)/C)C
• InChI: InChI=1S/C53H84NO14P/c1-32-18-14-13-15-19-33(2)44(63-8)30-40-23-21-38(7)53(61,67-40)50(58)51(59)54-25-17-16-20-41(54)52(60)66-45(35(4)28-39-22-24-43(46(29-39)64-9)68-69(11,12)62)31-42(55)34(3)27-37(6)48(57)49(65-10)47(56)36(5)26-32/h13-15,18-19,27,32,34-36,38-41,43-46,48-49,57,61H,16-17,20-26,28-31H2,1-12H3/b15-13+,18-14+,33-19+,37-27+/t32-,34-,35-,36-,38-,39+,40?,41+,43-,44-,45+,46-,48-,49+,53-/m1/s1
• InChIKey: BUROJSBIWGDYCN-CJEVDZHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 dimethylphosphinate
• IUPAC Traditional name: (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 dimethylphosphinate
• Synonyms: Rapamycin 42-(Dimethylphosphinate); Deforolimus; AP 23573; MK 8669; Ridaforolimus, >80%

Database IDs

• CAS Number: 572924-54-0
• PubChem SID: 164233445
• PubChem CID: 71752077

CALCULATED PROPERTIES

• Acid pKa: 9.963753
• H Acceptors: 12
• H Donor: 2
• LogD (pH = 5.5): 7.386385
• LogD (pH = 7.4): 7.3852167
• Log P: 7.3864
• Molar Refractivity: 267.9831 cm^3
• Polarizability: 104.7151 Å^3
• Polar Surface Area: 201.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 95-98°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R495850

An immunosupressant and is currently being investigated for use in cancer treatments. Ridaforolimus may act as a regulator of protein synthesis, cell proliferation, cell cycle progression and cell survival. Ridaforolimus, was formerly known as Deforolimus

REFERENCES

• Gadducci, A., et al.: Gynecol. Endocrinol., 24, 239 (2008)
• Gridelli, C., et al.: Oncol., 13, 139 (2008)
• Mita, M., et al.: J. Clin. Oncol., 26, 361 (2008)
• Hartford, C., et al.: Clin. Canc. Res., 15, 1428 (2008)