CAS 16837-52-8|Matrine N-oxide|Oxymatrine|oxymatrine|(1R,2R,9S,17S)-7,13$l^{5}-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,13-dione|Matrine 1beta-oxide|Matrine oxide|(1R,2R,9S,17S)-6-oxo-7...

General Information

Structure

Molecular Formula

C₁₅H₂₄N₂O₂

Molecular Mass

264.36326

Exact Mass

264.18377802

Charge

InChI

InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1

InChIKey

XVPBINOPNYFXID-LHDUFFHYSA-N

Canonic Smiles

O=C1CCC[C@H]2N1C[C@@H]1CCC[N+]3([C@@H]1[C@@H]2CCC3)[O-]

Isomeric Smiles

C1CC[N+]2([C@H]3[C@@H]1CN1[C@@H]([C@H]3CCC2)CCCC1=O)[O-]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.04851039

LogD (pH = 7.4)

-0.04844866

Log P

-0.04844787

Molar Refractivity

73.4934

Polarizability

28.323685

Polar Surface Area

47.19

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Matrine N-oxideOxymatrineMatrine 1beta-oxideMatrine oxide(4(1)S,7aS,13aR,13bR)-10-oxohexadecahydrodipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine 4-oxideAmmothamnineOxymatrineMatrine N -oxidePachycarpidine

IUPAC Traditional name

oxymatrine (1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-13-ium-13-olate

IUPAC name

(1R,2R,9S,17S)-7,13$l^{5}-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,13-dione (1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-13-ium-13-olate (1R,2R,9S,17S)-7,13λ⁵-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecane-6,13-dione

Names and Identifiers

Registration numbers

CAS Number

16837-52-8

PubChem CID

114850

PubChem SID

162037887

Registration numbers

Properties

Product Information

Salt Data

Free Base

Biological Source

Alkaloid from Sophora flavescens, Sophora macrocarpa, Ammothamnus lehmannii, Euchresta horsfeldii and other plants (Leguminosae)

Application(s)

Antiulcer

Have effects on liver fibrosis

Safety Information

Storage Condition

-20°C

Physical Property

Powder

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2338

Research Area: Immunology
Biological Activity:
Oxymatrine(Matrine N-oxide) is one of components of the root of Sophora flavescens. Sophora flavescens is a species of plant in the genus Sophora. Ku shen (the root) or kushenin (a flavonoid compound) is a typical traditional Chinese medicinethat is found in this plant. It is commonly used for the treatment of viral hepatitis, cancer, viral myocarditis, gastrointestinal hemorrhage and skin diseases (such as colpitis, psoriasis and eczema). Its roots contain quinolizidine alkaloids, includying matrine and its oxide, that interfere TNF-alpha and IL-6, suggesting that oxymatrine may inhibit the expression of the above pro-inflammatory cytokines. Matrine also inhibited expression of Substance P and NK-1R in a human model of skin inflammation, as well as acting as an agonist at mu and kappa opioid receptors. [1]

Molecule Details

References

PubChem Literature

From Data Sources

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

• Ibragimov, B.T. et al., Khim. Prir. Soedin., 1979, 15, 416; Chem. Nat. Compd. (Engl. Transl.), 1979, 15, 368, (cryst struct)

• Aslanov, A. et al., CA, 1967, 67, 71108, (oxide)

• Schtte, H.R. et al., Annalen, 1965, 685, 194, (biosynth)

• Sakamoto, T. et al., Chem. Pharm. Bull., 1986, 34, 2018, (synth)

• Kojima, R. et al., Chem. Pharm. Bull., 1970, 18, 2555, (pharmacol)

• Mandell, L. et al., J.A.C.S., 1965, 87, 5234, (synth)

• Abdusalamov, B.A., Khim. Prir. Soedin., 1984, 20, 3; Chem. Nat. Compd. (Engl. Transl.), 1984, 20, 1, (biosynth)