CAS 475-81-0|(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene|glaucine|GLAUCINE|(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetra...

基本信息

化学结构

分子式

C₂₁H₂₅NO₄

分子量

355.4275

精确质量

355.17835829

电荷

InChI

InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1

InChIKey

RUZIUYOSRDWYQF-HNNXBMFYSA-N

Canonic Smiles

COc1cc2-c3c(OC)c(OC)cc4c3[C@H](Cc2cc1OC)N(C)CC4

Isomeric Smiles

CN1CCc2cc(c(c3c2[C@@H]1Cc1c3cc(c(c1)OC)OC)OC)OC

计算属性

JChem

LogD (pH = 7.4)

2.92

LogD (pH = 5.5)

1.55

Log P

3.07

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

7.01

极化表面积

40.16

极化性

40.05

摩尔折射率

101.88

LOG S

-3.49

数据来源

名称和标识

IUPAC标准名

(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene

IUPAC传统名

glaucine (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene

别名

GLAUCINE(S)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolineGlaucine1,2,9,10-TetramethoxyaporphineS-(+)-Glaucine1,2,9,10-Tetramethoxy-6a-alpha-aporphineBoldine dimethyl etherGlaucined-Glaucine(S)-glaucine

名称和标识

数据登录号

EC号

CAS号

PubChem SID

PubChem CID

BRENDA数据库

2.1.1.3377.6.2.22.4.2.4

PubMed文献链接

2629714027399666269751102431742927397763239884888099963275589752567001625709212248971062527728125272947231945029600725256377622697758523303745

KEGG ID

BKMS React数据库

BRENDA Ligand数据库

CHEBI ID

KNApSAcK数据库

Reaxys Registry

CompTox数据库

ACToR数据库

SureChEMBL数据库

CHEMBL

KEGG DRUG Database

数据登录号

化合物性质

产品相关信息

质检报告

下载链接

应用领域

Antifungal agent

Shows antithrombotic, analgesic and antiinflammatory activity

Antitussive agent with similar potency to Codeine.

生物来源

Alkaloid from a wide variety of genera in the Annonaceae ( Alphonsea, Annona, Polyalthia, Schefferomitra, Uvaria ), Berberidaceae ( Berberis, Mahonia ), Euphorbiaceae ( Croton ), Fumariaceae ( Corydalis, Dicentra ), Lauraceae ( Beilschmiedia, Ocotea, Litsea ), Magnoliaceae ( Liriodendron, Magnolia ), Menispermaceae ( Chasmanthera ), Papaveraceae ( Glaucium, Papaver ), Ranunculaceae ( Thalictrum, Aconitum ), Rhamnaceae ( Colubrina ) and Monimiaceae ( Hedycaria )

纯度

98.5

理化性质

熔点

118°C

外观

Powder

药理学性质

生物活性机理

PDE4 inhibitor

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

MP Biomedicals

05223708

MP Biomedicals Rare Chemical collection

GNC

An aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups.

描述信息

参考文献

PubChem文献

数据源提供

• Guinaudeau, H. et al., J. Nat. Prod., 1975, 38, 275; 290; 1979, 42, 325; 329, (cmr, uv, rev)

• Ricca, G. et al., Gazz. Chim. Ital., 1979, 109, 1, (cmr)

• Aleshinskaya, E.E., Khim.-Farm. Zh., 1976, 10, 144, (pharmacol)

• Davis, P.J. et al., J.C.S. Perkin 1, 1977, 1, (synth, ms)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 747

• Estvez, J.C. et al., Tetrahedron, 1994, 50, 2107, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TDI475

• Baarschers, W.H. et al., J.C.S., 1964, 4478, (pmr, ms)

• Czarnocki, Z. et al., Can. J. Chem., 1987, 65, 2356, (synth)

• Ozaki, Y. et al., Chem. Pharm. Bull., 1993, 41, 481, (synth)

• Jackson, A.H. et al., J.C.S.(C), 1966, 2061, (synth, pmr, uv)

• Gottlieb, L. et al., J.O.C., 1990, 55, 5659, (synth)

• Ivorra, M.D. et al., Br. J. Pharmacol., 1992, 106, 387, (pharmacol)

• Oralla, F. et al., Br. J. Pharmacol., 1993, 110, 943; 1995, 114, 1419, (pharmacol)

• Kametani, T. et al., Tetrahedron, 1969, 25, 3667, (synth, ir, uv)

• Gupta, S. et al., Synth. Commun., 1989, 19, 393, (synth)

• Kase, Y. et al., Arzneim.-Forsch., 1983, 33, 936; 947, (pharmacol)

• Hartenstein, J. et al., Angew. Chem., 1977, 89, 739, (synth)

• Go, J., Yakugaku Zasshi, 1930, 50, 933, (isol)

• Kerr, K.M. et al., J. Nat. Prod., 1986, 49, 576, (pmr)

• Premila, M.S. et al., Indian J. Chem., Sect. B, 1976, 14, 134, (synth)

• Corrodi, H. et al., Helv. Chim. Acta, 1956, 39, 889, (abs config)

• Shamma, M. et al., J. Pharm. Sci., 1968, 57, 262, (isol, ir)

• Comins, D.L. et al., Tetrahedron, 1997, 48, 16327-16340, (synth)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

IUPAC传统名

别名

数据登录号

EC号

CAS号

PubChem SID

PubChem CID

BRENDA数据库

2.1.1.3377.6.2.22.4.2.4

PubMed文献链接

2629714027399666269751102431742927397763239884888099963275589752567001625709212248971062527728125272947231945029600725256377622697758523303745

KEGG ID

BKMS React数据库

BRENDA Ligand数据库

CHEBI ID

KNApSAcK数据库

Reaxys Registry

CompTox数据库

ACToR数据库

SureChEMBL数据库

CHEMBL

KEGG DRUG Database

描述信息

MP Biomedicals Rare Chemical collection

GNC

An aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups.

参考文献

PubChem文献

数据源提供

• Guinaudeau, H. et al., J. Nat. Prod., 1975, 38, 275; 290; 1979, 42, 325; 329, (cmr, uv, rev)

• Ricca, G. et al., Gazz. Chim. Ital., 1979, 109, 1, (cmr)

• Aleshinskaya, E.E., Khim.-Farm. Zh., 1976, 10, 144, (pharmacol)

• Davis, P.J. et al., J.C.S. Perkin 1, 1977, 1, (synth, ms)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 747

• Estvez, J.C. et al., Tetrahedron, 1994, 50, 2107, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TDI475

• Baarschers, W.H. et al., J.C.S., 1964, 4478, (pmr, ms)

• Czarnocki, Z. et al., Can. J. Chem., 1987, 65, 2356, (synth)

• Ozaki, Y. et al., Chem. Pharm. Bull., 1993, 41, 481, (synth)

• Jackson, A.H. et al., J.C.S.(C), 1966, 2061, (synth, pmr, uv)

• Gottlieb, L. et al., J.O.C., 1990, 55, 5659, (synth)

• Ivorra, M.D. et al., Br. J. Pharmacol., 1992, 106, 387, (pharmacol)

• Oralla, F. et al., Br. J. Pharmacol., 1993, 110, 943; 1995, 114, 1419, (pharmacol)

• Kametani, T. et al., Tetrahedron, 1969, 25, 3667, (synth, ir, uv)

• Gupta, S. et al., Synth. Commun., 1989, 19, 393, (synth)

• Kase, Y. et al., Arzneim.-Forsch., 1983, 33, 936; 947, (pharmacol)

• Hartenstein, J. et al., Angew. Chem., 1977, 89, 739, (synth)

• Go, J., Yakugaku Zasshi, 1930, 50, 933, (isol)

• Kerr, K.M. et al., J. Nat. Prod., 1986, 49, 576, (pmr)

• Premila, M.S. et al., Indian J. Chem., Sect. B, 1976, 14, 134, (synth)

• Corrodi, H. et al., Helv. Chim. Acta, 1956, 39, 889, (abs config)

• Shamma, M. et al., J. Pharm. Sci., 1968, 57, 262, (isol, ir)

• Comins, D.L. et al., Tetrahedron, 1997, 48, 16327-16340, (synth)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

质检报告

下载链接

应用领域

Antifungal agent

Shows antithrombotic, analgesic and antiinflammatory activity

Antitussive agent with similar potency to Codeine.

生物来源

纯度

98.5

理化性质

熔点

118°C

外观

Powder

药理学性质

生物活性机理

PDE4 inhibitor

化合物信息

ID:112389