化合物信息

ID:72606

基本信息

化学结构

分子式

C₁₅H₂₂O₅

分子量

282.33218

精确质量

282.1467238

电荷

InChI

InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14+,15-/m1/s1

InChIKey

BLUAFEHZUWYNDE-DKGJTOOQSA-N

Canonic Smiles

O=C1O[C@@H]2O[C@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3

Isomeric Smiles

[C@]12(O[C@@H]3[C@]4([C@@H](CC1)[C@@H](CC[C@H]4[C@H](C(=O)O3)C)C)OO2)C

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

3.114058

LogD (pH = 7.4)

3.114058

Log P

3.114058

摩尔折射率

68.6817

极化性

28.359936

极化表面积

53.99

可自由旋转的化学键

里宾斯基五规则

true

数据来源

产品目录

学术数据

数据来源

名称和标识

别名

CoartemArtemisinin(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12H)-oneQing Hau SauQinghaosuArteannuinArtemisinin

IUPAC标准名

(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-one (1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one

IUPAC传统名

名称和标识

数据登录号

CAS号

63968-64-9

PubChem SID

162037531

PubChem CID

9838675

数据登录号

化合物性质

产品相关信息

成盐信息

Free Base

生物来源

Constit. of Artemisia annua (Qinghaosu)

应用领域

Antimalarial agent

Shows advantages for use against drug-resistant malarial strains

纯度

98.5

安全信息

-20°C

药理学性质

Inhibitor of PfATP6, a SERCA-type enzyme

Reactive oxygen radicals producer

理化性质

Cryst.

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

Selleck Chemicals

S1282

Research Area: Infection
Biological Activity:
Artemisinin is a drug used to treat multi-drug resistant strains of falciparum malaria (as well as increasingly vivax malaria). The compound is isolated from the plant Artemisia annua, a herb described in Chinese traditional medicine, though it is usually chemically modified and combined with other medications. The drug is also being studied as a treatment for cancer. [1]

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Artemisinin

• El-Feraly, F.S. et al., Phytochemistry, 1986, 25, 2777, (biosynth)

• Akhila, A. et al., Phytochemistry, 1987, 26, 1927, (biosynth)

• Nowak, D.M. et al., Tetrahedron, 1998, 54, 319-336, (synth)

• Wu, Y. et al., Acc. Chem. Res., 2002, 35, 255-259, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1163B, (nmr)

• Zhou, W.-S., Pure Appl. Chem., 1986, 58, 817, (synth)

• Gu, H. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 657, (rev, pharmacol)

• Zaman, S.S. et al., Heterocycles, 1991, 32, 1593, (rev)

• Butler, A.R. et al., Chem. Soc. Rev., 1992, 21, 85, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 396

• Avery, M.A. et al., J.A.C.S., 1992, 114, 974, (synth)

• Hien, T.T. et al., Lancet, 1993, 341, 603, (rev)

• Sangwan, R.S. et al., Phytochemistry, 1993, 34, 1301, (biosynth)

• Constantino, M.G. et al., Synth. Commun., 1996, 26, 321, (synth, ir, pmr, cmr, ms)

• Zhou, W.-S. et al., Acc. Chem. Res., 1994, 27, 211, (rev, synth)

• Zhongshan, W. et al., Can. J. Chem., 1985, 63, 3070, (pmr, cmr)

• Klayman, D.L., Science (Washington, D.C.), 1985, 228, 1049, (rev, pharmacol)

• Xing-Xiang, X. et al., Tetrahedron, 1986, 42, 819, (synth)

• Ye, B. et al., Chem. Comm., 1990, 726, (synth)

• Nair, M.S.R. et al., J. Nat. Prod., 1993, 56, 1559, (biosynth)

• Chew, S.Y. et al., Tet. Lett., 1993, 34, 4435, (synth)

• Vandenberghe, D.R. et al., J. Nat. Prod., 1995, 58, 798, (isol)

• Ziffer, H. et al., Prog. Chem. Org. Nat. Prod., 1997, 72, 121-214, (rev)

• Blasko, G. et al., J. Nat. Prod., 1988, 51, 1273, (pmr, cmr)

• Roth, R.J. et al., J. Nat. Prod., 1989, 52, 1183, (synth)

• Ranasinghe, A. et al., J. Nat. Prod., 1993, 56, 552, (ms)

• Haynes, R.K. et al., Acc. Chem. Res., 1997, 30, 73-79, (rev)

• Robert, A. et al., Chem. Soc. Rev., 1998, 27, 273-279, (rev)

• Dayan, F.E. et al., Phytochemistry, 1999, 50, 607, (activity)

• Luo, X.D. et al., Med. Res. Rev., 1987, 7, 29, (rev, synth, struct, pharmacol)

• Lansbury, P.T. et al., Tet. Lett., 1992, 33, 1029, (synth)

• Wallaart, T.E. et al., J.O.C., 1999, 62, 430-433, (biosynth)

• Zhou, W.-S. et al., Huaxue Xuebao, 2000, 58, 135-143; CA, 2000, 132, 265303, (rev, synth)

• Schmid, G. et al., J.A.C.S., 1983, 105, 624, (synth)

• Ravindranathan, T. et al., Tet. Lett., 1990, 31, 755, (synth)

• Chan, K.L. et al., Phytochemistry, 1997, 46, 1209-1214, (cryst struct)

• Bharel, S. et al., J. Nat. Prod., 1998, 61, 633-636, (synth)

• Bouwmeester, H.J. et al., Phytochemistry, 1999, 52, 843-854, (biosynth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ARL375; ARL425

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

数据来源

• 产品目录

• 学术数据

名称和标识

• 别名

• IUPAC标准名

• IUPAC传统名

数据登录号

• CAS号

• PubChem SID

• PubChem CID

化合物性质

• 产品相关信息

• 安全信息

• 药理学性质

• 理化性质

• Selleck Chemicals

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

学术数据

PubChem

9838675

别名

CoartemArtemisinin(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12H)-oneQing Hau SauQinghaosuArteannuinArtemisinin

IUPAC标准名

IUPAC传统名

PubChem SID

162037531

Selleck Chemicals

S1282

数据源提供

• http://en.wikipedia.org/wiki/Artemisinin

• El-Feraly, F.S. et al., Phytochemistry, 1986, 25, 2777, (biosynth)

• Akhila, A. et al., Phytochemistry, 1987, 26, 1927, (biosynth)

• Nowak, D.M. et al., Tetrahedron, 1998, 54, 319-336, (synth)

• Wu, Y. et al., Acc. Chem. Res., 2002, 35, 255-259, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1163B, (nmr)

• Zhou, W.-S., Pure Appl. Chem., 1986, 58, 817, (synth)

• Gu, H. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 657, (rev, pharmacol)

• Zaman, S.S. et al., Heterocycles, 1991, 32, 1593, (rev)

• Butler, A.R. et al., Chem. Soc. Rev., 1992, 21, 85, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 396

• Avery, M.A. et al., J.A.C.S., 1992, 114, 974, (synth)

• Hien, T.T. et al., Lancet, 1993, 341, 603, (rev)

• Sangwan, R.S. et al., Phytochemistry, 1993, 34, 1301, (biosynth)

• Constantino, M.G. et al., Synth. Commun., 1996, 26, 321, (synth, ir, pmr, cmr, ms)

• Zhou, W.-S. et al., Acc. Chem. Res., 1994, 27, 211, (rev, synth)

• Zhongshan, W. et al., Can. J. Chem., 1985, 63, 3070, (pmr, cmr)

• Klayman, D.L., Science (Washington, D.C.), 1985, 228, 1049, (rev, pharmacol)

• Xing-Xiang, X. et al., Tetrahedron, 1986, 42, 819, (synth)

• Ye, B. et al., Chem. Comm., 1990, 726, (synth)

• Nair, M.S.R. et al., J. Nat. Prod., 1993, 56, 1559, (biosynth)

• Chew, S.Y. et al., Tet. Lett., 1993, 34, 4435, (synth)

• Vandenberghe, D.R. et al., J. Nat. Prod., 1995, 58, 798, (isol)

• Ziffer, H. et al., Prog. Chem. Org. Nat. Prod., 1997, 72, 121-214, (rev)

• Blasko, G. et al., J. Nat. Prod., 1988, 51, 1273, (pmr, cmr)

• Roth, R.J. et al., J. Nat. Prod., 1989, 52, 1183, (synth)

• Ranasinghe, A. et al., J. Nat. Prod., 1993, 56, 552, (ms)

• Haynes, R.K. et al., Acc. Chem. Res., 1997, 30, 73-79, (rev)

• Robert, A. et al., Chem. Soc. Rev., 1998, 27, 273-279, (rev)

• Dayan, F.E. et al., Phytochemistry, 1999, 50, 607, (activity)

• Luo, X.D. et al., Med. Res. Rev., 1987, 7, 29, (rev, synth, struct, pharmacol)

• Lansbury, P.T. et al., Tet. Lett., 1992, 33, 1029, (synth)

• Wallaart, T.E. et al., J.O.C., 1999, 62, 430-433, (biosynth)

• Zhou, W.-S. et al., Huaxue Xuebao, 2000, 58, 135-143; CA, 2000, 132, 265303, (rev, synth)

• Schmid, G. et al., J.A.C.S., 1983, 105, 624, (synth)

• Ravindranathan, T. et al., Tet. Lett., 1990, 31, 755, (synth)

• Chan, K.L. et al., Phytochemistry, 1997, 46, 1209-1214, (cryst struct)

• Bharel, S. et al., J. Nat. Prod., 1998, 61, 633-636, (synth)

• Bouwmeester, H.J. et al., Phytochemistry, 1999, 52, 843-854, (biosynth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ARL375; ARL425

产品相关信息

成盐信息

Free Base

生物来源

Constit. of Artemisia annua (Qinghaosu)

应用领域

Antimalarial agent

Shows advantages for use against drug-resistant malarial strains

纯度

98.5

安全信息

-20°C

药理学性质

Inhibitor of PfATP6, a SERCA-type enzyme

Reactive oxygen radicals producer

理化性质

Cryst.