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Barlerin (Standard)

CAT: 0804-HY-N0758RSize: 1 EachDry Ice: NoHazardous: No
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Description
Barlerin (Standard) is the analytical standard of Barlerin. This product is intended for research and analytical applications. Barlerin (8-O-Acetyl shanzhiside methyl ester) is an iridoid glucoside isolated from the leaves of Lamiophlomis rotata Kudo, a Chinese folk medicinal plant in Xi-zang. Barlerin (8-O-Acetyl shanzhiside methyl ester) could inhibt NF-κB.
CAS Number
57420-46-9
Product Name Alternative
8-O-Acetyl shanzhiside methyl ester (Standard)
UNSPSC
12352005
Target
Caspase; NF-κB; Reference Standards
Type
Reference Standards
Related Pathways
Apoptosis; NF-κB; Others
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/barlerin-standard.html
Smiles
O[C@H]([C@@H](O)[C@@H]1O)[C@](O[C@@H]1CO)([H])O[C@H]2[C@@]([C@@]3(C)OC(C)=O)([H])[C@@]([C@H](O)C3)([H])C(C(OC)=O)=CO2
Molecular Formula
C19H28O12
Molecular Weight
448.42
References & Citations
[1]Zhang L, et al. 8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti-inflammatory mechanism in diabetic rats. Basic Clin Pharmacol Toxicol. 2014 Dec;115 (6) :481-7.|[2]Kang ZC, et al. Cardioprotection with 8-O-acetyl shanzhiside methylester on experimental myocardial ischemia injury. Eur J Pharm Sci. 2012 Aug 30;47 (1) :124-30.|[3]Jiang WL, et al. Effect of 8-O-acetyl shanzhiside methylester increases angiogenesis and improves functional recovery after stroke. Basic Clin Pharmacol Toxicol. 2011 Jan;108 (1) :21-7.|[4]Fan PC, et al. A new anti-fibrinolytic hemostatic compound 8-O-acetyl shanzhiside methylester extracted from Lamiophlomis rotata. J Ethnopharmacol. 2016 Jul 1;187:232-8.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Barlerin

8-O-Acetylshanzhiside methyl ester has been reported in Barleria lupulina, Lamium garganicum, and other organisms with data available.

CAS Number57420-46-9
PubChem CID162823
IUPAC Namemethyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Molecular FormulaC19H28O12
Molecular Weight448.4
XLogP-2
Topological Polar Surface Area181
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Heavy Atom Count31
Formal Charge0
Complexity725
SMILES
CC(=O)O[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C
InChI
InChI=1S/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1
InChIKey
ARFRZOLTIRQFCI-NGQYDJQZSA-N
Chemical Structure
2D Structure
2D structure of Barlerin
CAS: 57420-46-9
CID: 162823
Formula: C19H28O12
MW: 448.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight448.4
XLogP3-2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass448.15807632
Monoisotopic Mass448.15807632
Topological Polar Surface Area181 Ų
Heavy Atom Count31
Formal Charge0
Complexity725
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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