(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30R,32S,35R)-1,18-dihydroxy-30-(2H3)methoxy-19-methoxy-12-[(2R)-1-[(1S,3R,4R)-3-methoxy-4-(1H-1,2,3,4-tetrazol-1-yl)cyclohexyl]propan-2-yl]-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: 179680
• Molecular Formular: C52H79N5O12
• Molecular Mass: 966.20996
• Monoisotopic Mass: 965.57252299
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@H](C)C[C@H]1C[C@H]([C@@H](CC1)n1nnnc1)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]1n1cnnn1)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/C52H79N5O12/c1-31-16-12-11-13-17-32(2)43(65-8)28-39-21-19-37(7)52(64,69-39)49(61)50(62)56-23-15-14-18-41(56)51(63)68-44(34(4)26-38-20-22-40(45(27-38)66-9)57-30-53-54-55-57)29-42(58)33(3)25-36(6)47(60)48(67-10)46(59)35(5)24-31/h11-13,16-17,25,30-31,33-35,37-41,43-45,47-48,60,64H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,32-17+,36-25+/t31-,33-,34-,35-,37-,38+,39?,40-,41+,43-,44+,45-,47-,48+,52-/m1/s1
• InChIKey: CGTADGCBEXYWNE-QQHXNUEISA-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-30-(^2H₃)methoxy-19-methoxy-12-[(2R)-1-[(1S,3R,4R)-3-methoxy-4-(1H-1,2,3,4-tetrazol-1-yl)cyclohexyl]propan-2-yl]-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-30-(^2H₃)methoxy-19-methoxy-12-[(2R)-1-[(1S,3R,4R)-3-methoxy-4-(1,2,3,4-tetrazol-1-yl)cyclohexyl]propan-2-yl]-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: (42S)-42-Deoxy-42-(1H-tetrazol-1-yl)rapamycin-d3; 42-(1-Tetrazolyl)rapamycin-d3; A 179578-d3; ABT 578-d3; Zotarolimus-d3

Database IDs

• PubChem SID: 164235590
• PubChem CID: 71753036

CALCULATED PROPERTIES

• Acid pKa: 9.963753
• H Acceptors: 14
• H Donor: 2
• LogD (pH = 5.5): 7.3221135
• LogD (pH = 7.4): 7.3209457
• Log P: 7.322129
• Molar Refractivity: 275.9365 cm^3
• Polarizability: 101.64848 Å^3
• Polar Surface Area: 218.8 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Z700802

Labelled Zotarolimus. A tetrazole-containing Rapamycin analog as immunomodulator and useful in the treatment of restenosis and immune and autoimmune diseases.

REFERENCES

• Moses, J., et al.: N. Engl. J. Med., 349, 1315 (2003)
• Ako, J., et al.: J. Am. Coll. Cardiol., 46, 1002 (2003)
• Wagner, et al.: Bioorg. Med. Chem. Lett., 15, 5340 (2003)
• Hong, M., et al.: Circulation, 113, 414 (2003)