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16837-52-8 molecular structure
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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

ChemBase ID: 72967
Molecular Formular: C15H24N2O2
Molecular Mass: 264.36326
Monoisotopic Mass: 264.18377802
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

Cite this record

CBID:72967 http://www.chembase.cn/molecule-72967.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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)-7,13λ5-diazatetracyclo[7.7.1.02,7.013,17]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
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
Synonyms
Matrine N-oxide
Matrine oxide
Matrine 1beta-oxide
Oxymatrine
Matrine N -oxide
Ammothamnine
Pachycarpidine
Oxymatrine
(4(1)S,7aS,13aR,13bR)-10-oxohexadecahydrodipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine 4-oxide
CAS Number
16837-52-8
PubChem SID
162037887
PubChem CID
114850

CALCULATED PROPERTIES

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 cm3
Polarizability 28.323685 Å3 Polar Surface Area 47.19 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Alkaloid from Sophora flavescens, Sophora macrocarpa, Ammothamnus lehmannii, Euchresta horsfeldii and other plants (Leguminosae) expand Show data source
Application(s)
Antiulcer expand Show data source
Have effects on liver fibrosis expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2338 external link
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 IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle 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

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INTERNET

INTERNET

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