(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编号: 1368
• 分子式: C53H83NO14
• 平均质量: 958.22442
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 商标名: Certican
• 别名: everolimus; Everolimus

登记号

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

理论计算性质

JChem

• 极化表面积: 204.66 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false
• Acid pKa: 9.96375
• 质子受体: 13
• 质子供体: 3
• LogD (pH = 5.5): 7.4038496
• LogD (pH = 7.4): 7.4026814
• Log P: 7.4038644
• 摩尔折射率: 261.7067 cm^3
• 极化性: 102.04239 Å^3

ALOGPS 2.1

• 溶解度: 1.63e-03 g/l
• Log P: 5.01
• LOG S: -5.77

详细说明

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

参考文献

• 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