(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one

• ChemBase ID: 72957
• Molecular Formular: C15H24N2O
• Molecular Mass: 248.36386
• Monoisotopic Mass: 248.1888634
• SMILES: C1CCN2[C@H]3[C@@H]1CN1[C@@H]([C@H]3CCC2)CCCC1=O
• Canonical SMILES: O=C1CCC[C@H]2N1C[C@@H]1CCCN3[C@@H]1[C@@H]2CCC3
• InChI: InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-/m0/s1
• InChIKey: ZSBXGIUJOOQZMP-JLNYLFASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one; (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadecan-6-one
• IUPAC Traditional name: matrine; (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadecan-6-one
• Synonyms: (+)-Matrine; Matrine; Matridin-15-one; Sophocarpidine; Matrine; Matridin-15-one. Lupanidine; Lupanidine

Database IDs

• CAS Number: 519-02-8
• MDL Number: MFCD00210527
• PubChem SID: 162037877
• PubChem CID: 91466
• CHEMBL: 204860
• Chemspider ID: 553788
• Wikipedia Title: Matrine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.3545308
• LogD (pH = 7.4): -1.248441
• Log P: 1.0759273
• Molar Refractivity: 71.4485 cm^3
• Polarizability: 28.175423 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C
• RTECS: OQ1754000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Legal Status: Unscheduled
• Mechanism of Action: Cholinergic; Sodium and calcium channel blocker

Product Information

• Salt Data: Free Base
• Biological Source: Alkaloid from roots of Sophora flavescens (Leguminosae)
• Application(s): Antibacterial; Antineoplastic; Antiulcer
• Empirical Formula (Hill Notation): C15H24N2O

DETAILS

Selleck Chemicals - S2322

Research Area: Cardiovascular Disease , Neurological Disease
Biological Activity:
Matrine((+)-Matrine) is an alkaloid found in plants from the Sophora family. It has a variety of pharmacological effects, including anti-cancer effects, and action as a kappa opioid receptor agonist. [1]

Sigma Aldrich - M5319

Biochem/physiol Actions
Matrine is an alkaloid that is one of the major components in the root of the saphoro plant. Matrine has been studied for possible antiviral efficacy against hepatitis B and C, as well as impact against some skin diseases and forms of cancer.

REFERENCES

• http://en.wikipedia.org/wiki/Matrine
• Bohlmann, F. et al., Chem. Ber., 1958, 91, 2176; 2189; 1975, 108, 1043, (ir, struct, config, cmr)
• Schtte, H.R. et al., Annalen, 1965, 685, 194, (biosynth)
• Mandell, L. et al., J.A.C.S., 1965, 87, 5234, (synth)
• Kojima, R. et al., Chem. Pharm. Bull., 1970, 18, 2555, (pharmacol)
• Vul'fson, N.S. et al., Khim. Geterotsikl. Soedin., 1974, 251; CA, 81, 13678z, (ms)
• Ueno, A. et al., Chem. Pharm. Bull., (footnote), 1975, 23, 2560, (abs config)
• Morinaga, K. et al., Chem. Pharm. Bull., 1978, 26, 2483, (pmr)
• Ibragimov, B.T. et al., Khim. Prir. Soedin., 1979, 15, 416; Chem. Nat. Compd. (Engl. Transl.), 1979, 15, 368, (cryst struct)
• Leeper, F.J. et al., Can. J. Chem., 1981, 59, 106, (biosynth)
• Ibragimov, B.T. et al., Khim. Prir. Soedin., 1982, 18, 71; Chem. Nat. Compd. (Engl. Transl.), 1982, 18, 66, (rev, stereochem)
• Abdusalamov, B.A., Khim. Prir. Soedin., 1984, 20, 3; Chem. Nat. Compd. (Engl. Transl.), 1984, 20, 1, (biosynth)
• Sakamoto, T. et al., Chem. Pharm. Bull., 1986, 34, 2018, (synth)
• Gonnella, N.C. et al., Magn. Reson. Chem., 1988, 26, 185, (pmr, cmr)