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Asperuloside

CAT: 0804-HY-N1382-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N1382-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Asperuloside is an iridoid isolated from Hedyotis diffusa, with anti-inflammatory activity. Asperuloside inhibits inducible nitric oxide synthase (iNOS), suppresses NF-κB and MAPK signaling pathways[1].
CAS Number
14259-45-1
UNSPSC
12352005
Hazard Statement
H302
Target
NO Synthase
Type
Natural Products
Related Pathways
Immunology/Inflammation
Applications
COVID-19-immunoregulation
Field of Research
Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/asperuloside.html
Purity
99.69
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : 25 mg/mL (ultrasonic)
Smiles
O=C1O[C@]2([H])[C@@]3([H])[C@](C(COC(C)=O)=C2)([H])[C@H](O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)OC=C13
Molecular Formula
C18H22O11
Molecular Weight
414.36
Precautions
H302
References & Citations
[1]He J, et al. Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages. Int J Mol Sci. 2018 Jul 12;19 (7) .|[2]Ishaq M, et al. Asperuloside Enhances Taste Perception and Prevents Weight Gain in High-Fat Fed Mice. Front Endocrinol (Lausanne) . 2021 Apr 13;12:615446.|[3]Rong C, et al. Asperuloside exhibits a novel anti-leukemic activity by triggering ER stress-regulated apoptosis via targeting GRP78. Biomed Pharmacother. 2020 May;125:109819.|[4]Qiu J, et al. Pretreatment with the compound asperuloside decreases acute lung injury via inhibiting MAPK and NF-κB signaling in a murine model. Int Immunopharmacol. 2016 Feb;31:109-15.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
INOS

Chemical Information

Asperuloside

Asperuloside is a iridoid monoterpenoid glycoside isolated from Galium verum. It has a role as a metabolite. It is a beta-D-glucoside, a gamma-lactone, an acetate ester, an iridoid monoterpenoid and a monosaccharide derivative.

CAS Number14259-45-1
PubChem CID84298
IUPAC Name[(4S,7S,8S,11S)-2-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-6-yl]methyl acetate
Molecular FormulaC18H22O11
Molecular Weight414.4
XLogP-2.4
Topological Polar Surface Area161
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count6
Heavy Atom Count29
Formal Charge0
Complexity746
SMILES
CC(=O)OCC1=C[C@H]2[C@H]3[C@@H]1[C@@H](OC=C3C(=O)O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChI
InChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1
InChIKey
IBIPGYWNOBGEMH-DILZHRMZSA-N
Chemical Structure
2D Structure
2D structure of Asperuloside
CAS: 14259-45-1
CID: 84298
Formula: C18H22O11
MW: 414.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight414.4
XLogP3-2.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count6
Exact Mass414.11621151
Monoisotopic Mass414.11621151
Topological Polar Surface Area161 Ų
Heavy Atom Count29
Formal Charge0
Complexity746
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
HY-N6246-01Asperulosidic Acid
HY-N6246RAsperulosidic Acid (Standard)

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CatalogName
BA6093-10Asperuloside
299959Asperuloside (Rubichloric acid)

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