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|(S)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetra...

General Information

Structure

Molecular Formula

C₂₁H₂₅NO₄

Molecular Mass

355.4275

Exact Mass

355.17835829

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

2.92

LogD (pH = 5.5)

1.55

Log P

3.07

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.01

Polar Surface Area

40.16

Polarizability

40.05

Molar Refractivity

101.88

LOG S

-3.49

Data Source

Names and Identifiers

IUPAC name

(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 Traditional name

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

Synonyms

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

Names and Identifiers

Registration numbers

EC Number

CAS Number

PubChem SID

PubChem CID

BRENDA Ligand Database

218019206959

PubMed Citation Links

2755897523988488269775852431742927397763231945022489710623303745256377622570921226297140252729472567001625277281960072527399666269751108099963

CHEBI ID

BKMS React Database

KEGG ID

Reaxys Registry

BRENDA Database

2.1.1.3372.4.2.47.6.2.2

KEGG DRUG Database

SureChEMBL Database

CHEMBL

KNApSAcK Database

CompTox Database

ACToR Database

Registration numbers

Properties

Physical Property

Melting Point

118°C

Apperance

Powder

Safety Information

Risk Statements

R:22

European Hazard Symbols

Harmful (Xn)

MSDS Link

Download link

RTECS

CE0925000

Safety Statements

S:36/37/39

Product Information

Certificate of Analysis

Download link

Biological Source

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 )

Application(s)

Antifungal agent

Antitussive agent with similar potency to Codeine.

Shows antithrombotic, analgesic and antiinflammatory activity

98.5

Pharmacology Properties

Mechanism of Action

PDE4 inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

IUPAC Traditional name

Synonyms

Registration numbers

EC Number

CAS Number

PubChem SID

PubChem CID

BRENDA Ligand Database

218019206959

PubMed Citation Links

2755897523988488269775852431742927397763231945022489710623303745256377622570921226297140252729472567001625277281960072527399666269751108099963

CHEBI ID

BKMS React Database

KEGG ID

Reaxys Registry

BRENDA Database

2.1.1.3372.4.2.47.6.2.2

KEGG DRUG Database

SureChEMBL Database

CHEMBL

KNApSAcK Database

CompTox Database

ACToR Database

Molecule Details

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.

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Bioactivity

PubChem BioAssay

Properties

Physical Property

Melting Point

118°C

Apperance

Powder

Safety Information

Risk Statements

R:22

European Hazard Symbols

Harmful (Xn)

MSDS Link

Download link

RTECS

CE0925000

Safety Statements

S:36/37/39

Product Information

Certificate of Analysis

Download link

Biological Source

Application(s)

Antifungal agent

Antitussive agent with similar potency to Codeine.

Shows antithrombotic, analgesic and antiinflammatory activity

98.5

Pharmacology Properties

Mechanism of Action

PDE4 inhibitor

Molecule

ID:112389