(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-[2-hydroxy(2H4)ethoxy]-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

• ChemBase ID: 168834
• Molecular Formular: C53H83NO14
• Molecular Mass: 958.22442
• Monoisotopic Mass: 957.58135634
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@H](C)C[C@H]1C[C@H]([C@@H](CC1)OCCO)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: OCCO[C@@H]1CC[C@H](C[C@H]1OC)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/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40?,41+,43-,44-,45+,46-,48-,49+,53-/m1/s1
• InChIKey: HKVAMNSJSFKALM-SEZGQZKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-[2-hydroxy(^2H₄)ethoxy]-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• IUPAC Traditional name: (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-[2-hydroxy(^2H₄)ethoxy]-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• Synonyms: 40-O-(2-Hydroxyethyl-d4)rapamycin; 42-O-(2-Hydroxy)ethyl-d4 Rapamycin; Afinitor-d4; Certican-d4; RAD-d4; RAD 001-d4; SDZ-RAD-d4; XIENCE V-d4; Everolimus-d4

Database IDs

• PubChem SID: 162262966
• PubChem CID: 71316701

CALCULATED PROPERTIES

• Acid pKa: 9.96375
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 7.4038496
• LogD (pH = 7.4): 7.4026814
• Log P: 7.4038644
• Molar Refractivity: 261.7067 cm^3
• Polarizability: 102.04239 Å^3
• Polar Surface Area: 204.66 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 79-96°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - E945402

Macrolide immunosuppressant; derivative of Rapamycin. Inhibits cytokine-mediated lymphocyte proliferation.

REFERENCES

• Dumont, F.J., et al.: Curr. Opin. Invest. Drugs, 2, 1220 (2001)
• Kovarik, J. M., et al.: Clin. Pharmacol. Ther., 69, 48 (2001)
• Nashan, B., et al.: Ther. Drug Monit., 24, 53 (2001)