Home > Compound List > Compound details
5610-40-2 molecular structure
click picture or here to close

(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one

ChemBase ID: 155034
Molecular Formular: C13H15NO2
Molecular Mass: 217.2637
Monoisotopic Mass: 217.11027873
SMILES and InChIs

SMILES:
C1CCN2[C@H](C1)[C@]13C[C@@H]2C=CC1=CC(=O)O3
Canonical SMILES:
O=C1C=C2[C@@]3(O1)C[C@H](C=C2)N1[C@@H]3CCCC1
InChI:
InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1
InChIKey:
SWZMSZQQJRKFBP-WZRBSPASSA-N

Cite this record

CBID:155034 http://www.chembase.cn/molecule-155034.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one
IUPAC Traditional name
(-)-securinine
Synonyms
Securinine
CAS Number
5610-40-2
MDL Number
MFCD00078775
PubChem SID
162249172
PubChem CID
442872

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 442872 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -1.9773666  LogD (pH = 7.4) -0.68543625 
Log P 1.4055138  Molar Refractivity 61.3191 cm3
Polarizability 23.567463 Å3 Polar Surface Area 29.54 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: ≥25 mg/mL expand Show data source
Apperance
yellow powder expand Show data source
Optical Rotation
[α]/D -980 to -1015 ( C=1, MeOH) expand Show data source
RTECS
VS4115000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C13H15NO2 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - SML0055 external link
Biochem/physiol Actions
Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
    No data available
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle