(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 2,2,5-trimethyl-1,3-dioxane-5-carboxylate

• ChemBase ID: 178141
• Molecular Formular: C59H91NO16
• Molecular Mass: 1070.35094
• Monoisotopic Mass: 1069.63378584
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@@H](C[C@H]1C[C@H]([C@@H](CC1)OC(=O)C1(COC(OC1)(C)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]1OC(=O)C1(C)COC(OC1)(C)C)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/C59H91NO16/c1-35-19-15-14-16-20-36(2)47(69-11)31-43-24-22-41(7)59(68,76-43)53(64)54(65)60-26-18-17-21-44(60)55(66)74-48(32-45(61)37(3)28-40(6)51(63)52(71-13)50(62)39(5)27-35)38(4)29-42-23-25-46(49(30-42)70-12)75-56(67)58(10)33-72-57(8,9)73-34-58/h14-16,19-20,28,35,37-39,41-44,46-49,51-52,63,68H,17-18,21-27,29-34H2,1-13H3/b16-14+,19-15+,36-20+,40-28+/t35-,37-,38-,39-,41-,42+,43?,44+,46-,47-,48+,49-,51-,52+,59-/m1/s1
• InChIKey: YGGRYGCDSJUKRW-FNOGGREOSA-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 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• 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 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• Synonyms: Rapamycin 42-(2,2,5-Trimethyl-1,3-dioxane-5-carboxylate); Temsirolimus Acetonide

Database IDs

• CAS Number: 162635-03-2
• PubChem SID: 164234051
• PubChem CID: 71752353

CALCULATED PROPERTIES

• Polar Surface Area: 219.96 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 9.963753
• H Acceptors: 14
• H Donor: 2
• LogD (pH = 5.5): 8.832369
• LogD (pH = 7.4): 8.831201
• Log P: 8.832384
• Molar Refractivity: 289.2735 cm^3
• Polarizability: 113.22627 Å^3

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 89-91°C

Safety Information

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

DETAILS

Toronto Research Chemicals - T017970

Rapamycin 42-ester derivative.

REFERENCES

• Singh, K., et al.: J. Antibiot., 32, 630 (1979)
• Sehgal, S., et al.: Clin. Biochem., 31, 335 (1979)
• Abraham, R., et al.: Cell, 111, 9 (1979)