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72741-87-8 molecular structure
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(1S,2R,8R)-octahydroindolizine-1,2,8-triol

ChemBase ID: 131045
Molecular Formular: C8H15NO3
Molecular Mass: 173.2096
Monoisotopic Mass: 173.10519335
SMILES and InChIs

SMILES:
C1C[C@H](C2[C@@H]([C@@H](CN2C1)O)O)O
Canonical SMILES:
O[C@@H]1CN2C([C@@H]1O)[C@H](O)CCC2
InChI:
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7?,8-/m1/s1
InChIKey:
FXUAIOOAOAVCGD-DCDLSZRSSA-N

Cite this record

CBID:131045 http://www.chembase.cn/molecule-131045.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,8R)-octahydroindolizine-1,2,8-triol
IUPAC Traditional name
(1S,2R,8R)-octahydroindolizine-1,2,8-triol
Synonyms
(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
Swainsonine
CAS Number
72741-87-8
MDL Number
MFCD00017554
Beilstein Number
4175740
PubChem SID
24899832
162225323
24899779
PubChem CID
16219982

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16219982 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.284674  H Acceptors
H Donor LogD (pH = 5.5) -4.78174 
LogD (pH = 7.4) -3.4669168  Log P -1.4067957 
Molar Refractivity 43.1178 cm3 Polarizability 17.444298 Å3
Polar Surface Area 63.93 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
lyophilized powder expand Show data source
RTECS
NM2408666 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
≥98% (TLC) expand Show data source
Biological Source
from locoweed expand Show data source
from Metarrhizium anisopliae expand Show data source
from Rhizoctonia leguminicola expand Show data source
from synthetic expand Show data source
Empirical Formula (Hill Notation)
C8H15NO3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - S6640 external link
Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3
Sigma Aldrich - S8195 external link
Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.3 It inhibits glycoprotein processing4 and also acts as immune modulator.3,5
Swainsonine is an indolizidine alkaloid from the plant Metarrhizium anisopliae that is used as a potent α-mannosidase inhibitor1. Product S8195 has been used in chemical inhibition assays of CHO Lec2 cells to inhibit glycosylation 2.
Biochem/physiol Actions
Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity 1. It also inhibits glycoprotein processing.
Physical properties
Soluble in water, methanol, DMSO
Sigma Aldrich - S9263 external link
Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3
Sigma Aldrich - 86204 external link
Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II.1 It inhibits glycoprotein processing2 and also acts as immune modulator.1,3
Other Notes
Inhibitor of Golgi mannosidase II and hence glycoprotein biosynthesis4,5

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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