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3371-85-5 分子结构
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methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

ChemBase编号:4393
分子式:C43H52N4O5
平均质量:704.89678
单一同位素质量:704.39377078
SMILES和InChIs

SMILES:
O(C(=O)[C@]12[C@H]3N(C[C@H](C1)C[C@@H]3CC)CCc1c2[nH]c2c1cc(OC)c(c2)[C@H]1C[C@@H]2C([C@H](N(C/C/2=C/C)C)Cc2c1[nH]c1c2cccc1)C(=O)OC)C
Canonical SMILES:
COC(=O)C1[C@H]2C[C@H](c3cc4[nH]c5c(c4cc3OC)CCN3[C@@H]4[C@]5(C[C@H](C[C@@H]4CC)C3)C(=O)OC)c3c(C[C@H]1N(C/C/2=C/C)C)c1ccccc1[nH]3
InChI:
InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28-,31+,35+,37?,40-,43+/m0/s1
InChIKey:
VCMIRXRRQJNZJT-XRMSBCOFSA-N

引用这个纪录

CBID:4393 http://www.chembase.cn/molecule-4393.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
IUPAC传统名
methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
商标名
MMH
别名
Vocamine
Voacanginine
MMH
voacamine
Voacamine
CAS号
3371-85-5
PubChem SID
160967825
99443228
PubChem CID
11953931

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB04877 external link
PubChem 11953931 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 15.555076  质子受体
质子供体 LogD (pH = 5.5) 1.2435583 
LogD (pH = 7.4) 4.679502  Log P 6.2061973 
摩尔折射率 203.6844 cm3 极化性 81.28505 Å3
极化表面积 99.89 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 6.26  LOG S -5.34 
溶解度 3.23e-03 g/l 

分子性质

分子性质

生物活性(PubChem)

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB04877 external link
Item Information
Drug Groups approved; investigational
Description Voacamine is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. It is an antimalarial drug approved for use in several African countries. Voacamine is also under investigation for use in modulating multidrug-resistance in tumor cells.
Indication For the treatment of malaria. Also under investigation for the modulation of multidrug resistance in cancer cells.
Pharmacology Voacamine is an anti-malarial extracted from the Brazilian tree Peschiera fuchsiaefolia. In one study (PMID: 11180519), the in vivo antiplasmodial activity of voacamine was assessed in a 4-day test. It was shown to exhibit in vivo activity with 25.4% and 43.4% inhibition of parasitaemia with 2.5 and 10 mg/kg, respectively. In synchronized cultures, it was found to act on trophozoite and schizont stages of Plasmodium falciparum.
Voacamine is a bisindolic alkaloid under investigation for modulation of multidrug resistance to enhance anticancer drugs such as doxorubicin.
Affected Organisms
Plasmodium
References
Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. [Pubmed]
Meschini S, Condello M, Marra M, Formisano G, Federici E, Arancia G: Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. Epub 2006 Sep 16. [Pubmed]
Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. [Pubmed]

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Meschini S, Condello M, Marra M, Formisano G, Federici E, Arancia G: Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. Epub 2006 Sep 16. Pubmed
  • Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. Pubmed
  • Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. Pubmed
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专利

专利

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