CAS 53123-88-9|sirolimus|Rapamycin|(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,...

General Information

Structure

Molecular Formula

C₅₁H₇₉NO₁₃

Molecular Mass

914.17186

Exact Mass

913.55514159

Charge

0

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

Canonic 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

Isomeric 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

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

Polarizability

97.655174

Polar Surface Area

195.43

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

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

sirolimusrapamycinAntibiotic AY 22989Sirolimus

Brand Name

RapamycinRapamune

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

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

Names and Identifiers

Registration numbers

PubChem SID

160964218

PubChem CID

70789198

CAS Number

53123-88-9

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

4.3

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. 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

• 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

• Shuchman M: Trading restenosis for thrombosis? New questions about drug-eluting stents. N Engl J Med. 2006 Nov 9;355(19):1949-52. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:755