(1S,9R,15R,16E,18R,19R,21S,23R,24E,26E,28E,30S,32R,35S)-1,18-dihydroxy-12-[(2S)-1-[(1S,3R,4R)-4-(2-hydroxyethoxy)-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: 1368
• Molecular Formular: C53H83NO14
• Molecular Mass: 958.22442
• Monoisotopic Mass: 957.58135634
• SMILES: C1(=O)[C@@H]2N(C(=O)C(=O)[C@]3(O[C@H](CC[C@@H]3C)C[C@@H](/C(=C/C=C/C=C/[C@@H](C[C@@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)CC(O1)[C@@H](C)C[C@H]1C[C@H]([C@@H](CC1)OCCO)OC)C)/C)O)OC)C)C)/C)OC)O)CCCC2
• Canonical SMILES: OCCO[C@@H]1CC[C@H](C[C@H]1OC)C[C@@H](C1OC(=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-/m0/s1
• InChIKey: HKVAMNSJSFKALM-CYUZEOOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,15R,16E,18R,19R,21S,23R,24E,26E,28E,30S,32R,35S)-1,18-dihydroxy-12-[(2S)-1-[(1S,3R,4R)-4-(2-hydroxyethoxy)-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: (1S,9R,15R,16E,18R,19R,21S,23R,24E,26E,28E,30S,32R,35S)-1,18-dihydroxy-12-[(2S)-1-[(1S,3R,4R)-4-(2-hydroxyethoxy)-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: Certican
• Synonyms: everolimus; Everolimus

Database IDs

• CAS Number: 159351-69-6
• PubChem SID: 160964828
• PubChem CID: 70789204

CALCULATED PROPERTIES

JChem

• Polar Surface Area: 204.66 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• 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

ALOGPS 2.1

• Solubility (Water): 1.63e-03 g/l
• Log P: 5.01
• LOG S: -5.77

DETAILS

DrugBank - DB01590

• Drug Groups: approved; investigational
• Description: Everolimus is a derivative of Rapamycin (sirolimus), and works similarly to Rapamycin as an mTOR (mammalian target of rapamycin) inhibitor. It is currently used as an immunosuppressant to prevent rejection of organ transplants. In a similar fashion to other mTOR inhibitors Everolimus' effect is solely on the mTORC1 protein and not on the mTORC2 protein.
• Indication: Investigated for use/treatment in transplant (rejection) and renal cell carcinoma.
• Elimination: After a single dose of radiolabeled everolimus was given to transplant patients receiving cyclosporine, the majority (80%) of radioactivity was recovered from the feces and only a minor amount (5%) was excreted in urine.
• References: Kuhn B, Jacobsen W, Christians U, Benet LZ, Kollman PA: Metabolism of sirolimus and its derivative everolimus by cytochrome P450 3A4: insights from docking, molecular dynamics, and quantum chemical calculations. J Med Chem. 2001 Jun 7;44(12):2027-34. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Kuhn B, Jacobsen W, Christians U, Benet LZ, Kollman PA: Metabolism of sirolimus and its derivative everolimus by cytochrome P450 3A4: insights from docking, molecular dynamics, and quantum chemical calculations. J Med Chem. 2001 Jun 7;44(12):2027-34. Pubmed