(1R,9S,12S,15S,16E,18R,19R,21S,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

• ChemBase ID: 755
• Molecular Formular: C51H79NO13
• Molecular Mass: 914.17186
• Monoisotopic Mass: 913.55514159
• SMILES: C1[C@@H]2N(CCC1)C(=O)C(=O)[C@@]1(O[C@@H](CC[C@H]1C)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)C[C@H](OC2=O)[C@@H](C[C@@H]1CC[C@H]([C@@H](C1)OC)O)C)C)/C)O)OC)C)C)/C)O
• 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-MQWRTCEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,15S,16E,18R,19R,21S,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,15S,16E,18R,19R,21S,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
• Brand Name: Rapamune; Rapamycin
• Synonyms: Antibiotic AY 22989; sirolimus; rapamycin; Sirolimus

Database IDs

• CAS Number: 53123-88-9
• PubChem SID: 160964218
• PubChem CID: 70789198

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 4.85
• LOG S: -5.72
• Solubility (Water): 1.73e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.3

DETAILS

DrugBank - DB00877

• Drug Groups: approved; investigational
• Description: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to immunophilins. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties. [PubChem]
• Indication: For the prophylaxis of organ rejection in patients receiving renal transplants.
• Pharmacology: Sirolimus, a macrocyclic lactone produced by Streptomyces hygroscopicus, is an immunosuppressive agent indicated for the prophylaxis of organ rejection in patients receiving renal transplants. It is recommended that sirolimus be used in a regimen with cyclosporine and corticosteroids.
• Affected Organisms: Humans and other mammals
• Half Life: 57-63 hours
• Protein Binding: 92%
• References: Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. [Pubmed] ; Shuchman M: Trading restenosis for thrombosis? New questions about drug-eluting stents. N Engl J Med. 2006 Nov 9;355(19):1949-52. [Pubmed] ; Sun SY, Rosenberg LM, Wang X, Zhou Z, Yue P, Fu H, Khuri FR: Activation of Akt and eIF4E survival pathways by rapamycin-mediated mammalian target of rapamycin inhibition. Cancer Res. 2005 Aug 15;65(16):7052-8. [Pubmed] ; Chan S: Targeting the mammalian target of rapamycin (mTOR): a new approach to treating cancer. Br J Cancer. 2004 Oct 18;91(8):1420-4. [Pubmed] ; Graziani EI: Recent advances in the chemistry, biosynthesis and pharmacology of rapamycin analogs. Nat Prod Rep. 2009 May;26(5):602-9. Epub 2009 Mar 5. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Graziani EI: Recent advances in the chemistry, biosynthesis and pharmacology of rapamycin analogs. Nat Prod Rep. 2009 May;26(5):602-9. Epub 2009 Mar 5. Pubmed
• Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. Pubmed
• Shuchman M: Trading restenosis for thrombosis? New questions about drug-eluting stents. N Engl J Med. 2006 Nov 9;355(19):1949-52. Pubmed
• Sun SY, Rosenberg LM, Wang X, Zhou Z, Yue P, Fu H, Khuri FR: Activation of Akt and eIF4E survival pathways by rapamycin-mediated mammalian target of rapamycin inhibition. Cancer Res. 2005 Aug 15;65(16):7052-8. Pubmed
• Chan S: Targeting the mammalian target of rapamycin (mTOR): a new approach to treating cancer. Br J Cancer. 2004 Oct 18;91(8):1420-4. Pubmed