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(1R,2R,9S,17S)-7,13$l^{5}-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,13-dione
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ChemBase ID:
72967
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Molecular Formular:
C15H24N2O2
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Molecular Mass:
264.36326
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Monoisotopic Mass:
264.18377802
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SMILES and InChIs
SMILES:
C1CC[N+]2([C@H]3[C@@H]1CN1[C@@H]([C@H]3CCC2)CCCC1=O)[O-]
Canonical SMILES:
O=C1CCC[C@H]2N1C[C@@H]1CCC[N+]3([C@@H]1[C@@H]2CCC3)[O-]
InChI:
InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1
InChIKey:
XVPBINOPNYFXID-LHDUFFHYSA-N
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Cite this record
CBID:72967 http://www.chembase.cn/molecule-72967.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(1R,2R,9S,17S)-7,13$l^{5}-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,13-dione
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(1R,2R,9S,17S)-7,13λ5-diazatetracyclo[7.7.1.02,7.013,17]heptadecane-6,13-dione
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(1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-13-ium-13-olate
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IUPAC Traditional name
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oxymatrine
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(1R,2R,9S,17S)-6-oxo-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-13-ium-13-olate
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Synonyms
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Matrine N-oxide
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Matrine oxide
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Matrine 1beta-oxide
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Oxymatrine
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Matrine N -oxide
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Ammothamnine
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Pachycarpidine
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Oxymatrine
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(4(1)S,7aS,13aR,13bR)-10-oxohexadecahydrodipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine 4-oxide
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
H Acceptors
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2
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H Donor
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0
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LogD (pH = 5.5)
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-0.04851039
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LogD (pH = 7.4)
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-0.04844866
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Log P
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-0.04844787
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Molar Refractivity
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73.4934 cm3
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Polarizability
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28.323685 Å3
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Polar Surface Area
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47.19 Å2
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Rotatable Bonds
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0
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Selleck Chemicals
Selleck Chemicals -
S2338
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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] |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • http://en.wikipedia.org/wiki/Sophora_flavescens
- • 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)
- • Aslanov, A. et al., CA, 1967, 67, 71108, (oxide)
- • 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)
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PATENTS
PATENTS
PubChem Patent
Google Patent