(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-hydroxy-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: 177372
• Molecular Formular: C51H79NO13
• Molecular Mass: 914.17186
• Monoisotopic Mass: 913.55514159
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@H]([C@@H](C[C@H]1C[C@H]([C@@H](CC1)O)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]1O)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/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38?,39+,40-,42-,43+,44-,46-,47+,51-/m1/s1
• InChIKey: QFJCIRLUMZQUOT-KUYJZQLGSA-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-hydroxy-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-hydroxy-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: (-)-Rapamycin; AY 22989; Antibiotic AY 22989; Cypher; NSC 226080; RAPA; RPM; Rapammune; Rapamune; SIIA 9268A; Sirolimus; Wy 090217; Rapamycin

Database IDs

• CAS Number: 53123-88-9
• PubChem SID: 164233282
• PubChem CID: 9962928

CALCULATED PROPERTIES

• Acid pKa: 9.963728
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 7.4508247
• LogD (pH = 7.4): 7.4496565
• Log P: 7.45084
• Molar Refractivity: 250.6632 cm^3
• Polarizability: 97.655174 Å^3
• Polar Surface Area: 195.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R124000

A triene macrolide antibiotic isolated from Streptomyces hygroscopicus. Name derived from the native word for Easter Island, Rapa’Nui. Used as an immunosuppressant; antirestenotic. Sirolimus (INN/USAN), also known as rapamycin, is an immunosuppressant dru

REFERENCES

• Martel, P.R., et al.: Can. J. Physiol. Pharmacol., 55, 48 (1977)
• Carlson, R.P., et al.: J. Pharmacol. Exp. Ther., 266, 1125 (1977)
• Kahan, B.D., et al.: Lancet, 356, 194 (1977)
• Holmes, D.R., et al.: Circulation, 109, 634 (1977)