(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 3-hydroxy-2-[hydroxy(13C,2H2)methyl]-2-(13C,2H3)methyl(3-13C,2H2)propanoate

• ChemBase ID: 178140
• Molecular Formular: C56H87NO16
• Molecular Mass: 1033.26504451
• Monoisotopic Mass: 1032.61255022
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@H](C)C[C@H]1C[C@H]([C@@H](CC1)OC(=O)C([13CH2]O)([13CH2]O)[13CH3])OC)CC(=O)[C@@H](/C=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
• Canonical SMILES: CO[C@@H]1C[C@@H](CC[C@H]1OC(=O)C([13CH2]O)([13CH2]O)[13CH3])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/C56H87NO16/c1-33-17-13-12-14-18-34(2)45(68-9)29-41-22-20-39(7)56(67,73-41)51(63)52(64)57-24-16-15-19-42(57)53(65)71-46(30-43(60)35(3)26-38(6)49(62)50(70-11)48(61)37(5)25-33)36(4)27-40-21-23-44(47(28-40)69-10)72-54(66)55(8,31-58)32-59/h12-14,17-18,26,33,35-37,39-42,44-47,49-50,58-59,62,67H,15-16,19-25,27-32H2,1-11H3/b14-12+,17-13+,34-18+,38-26+/t33-,35-,36-,37-,39-,40+,41?,42+,44-,45-,46+,47-,49-,50+,56-/m1/s1/i8+1,31+1,32+1
• InChIKey: CBPNZQVSJQDFBE-VPCAMRPHSA-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 3-hydroxy-2-[hydroxy(^1^3C,^2H₂)methyl]-2-(^1^3C,^2H₃)methyl(3-^1^3C,^2H₂)propanoate
• 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 3-hydroxy-2-[hydroxy(^1^3C,^2H₂)methyl]-2-(^1^3C,^2H₃)methyl(3-^1^3C,^2H₂)propanoate
• Synonyms: Rapamycin 42-[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoate-13C3,d7; CCL-779-13C3,d7; Temsirolimus-13C3,d7

Database IDs

• PubChem SID: 164234050
• PubChem CID: 71752352

CALCULATED PROPERTIES

• Acid pKa: 9.96374
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 7.1299443
• LogD (pH = 7.4): 7.128776
• Log P: 7.1299596
• Molar Refractivity: 277.0665 cm^3
• Polarizability: 108.30001 Å^3
• Polar Surface Area: 241.96 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T017963

Labelled ester analog of Rapamycin.

REFERENCES

• Raymond, E., et al.: J. Clin. Oncol., 22, 2336 (2004)
• Galanis, E., et al.: J. Clin. Oncol., 23, 5294 (2005)