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Isoacteoside

CAT: 0804-HY-N0022-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0022-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products. Isoacteoside regulates the AKT/PI3K/m-TOR/NF-κB signaling pathway, induces apoptosis in OVCAR-3 cell. Isoacteoside exhibits antitumor, anti-inflammatory, anti-obesity and neuroprotective activities[1][2][3][4][5].
CAS Number
61303-13-7
Product Name Alternative
Isoverbascoside
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Akt; Amyloid-β; Apoptosis; COX; mTOR; NO Synthase; p38 MAPK; PI3K; Reactive Oxygen Species (ROS) ; Toll-like Receptor (TLR)
Type
Natural Products
Related Pathways
Apoptosis; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB; PI3K/Akt/mTOR
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Metabolic Disease; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Isoacteoside.html
Concentration
10mM
Purity
99.73
Solubility
DMSO : 175 mg/mL (ultrasonic) |H2O : ≥ 100 mg/mL
Smiles
OC1=CC(/C=C/C(OC[C@@H]2[C@@H](O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](OCCC4=CC=C(O)C(O)=C4)O2)=O)=CC=C1O
Molecular Formula
C29H36O15
Molecular Weight
624.59
Precautions
H302, H315, H319, H335
References & Citations
[1]Yu SY, et al. Caffeoylated phenylpropanoid glycosides from Brandisia hancei inhibit advanced glycation end product formation and aldose reductase in vitro and vessel dilation in larval zebrafish in vivo. Planta Med. 2013 Dec;79 (18) :1705-9.|[2]Gao H, Cui Y, Kang N, et al. Isoacteoside, a dihydroxyphenylethyl glycoside, exhibits anti-inflammatory effects through blocking toll-like receptor 4 dimerization. Br J Pharmacol. 2017;174 (17) :2880-2896. |[3]Yang X, Guo F, Peng Q, Liu Y, Yang B. Suppression of in vitro and in vivo human ovarian cancer growth by isoacteoside is mediated via sub-G1 cell cycle arrest, ROS generation, and modulation of AKT/PI3K/m-TOR signalling pathway. J BUON. 2019;24 (1) :285-290.|[4]Choi C G, et al. Anti-obesity effects of isoacteoside on 3T3-L1 adipocytes[J]. Applied Biological Chemistry, 2022, 65 (1) : 33.|[5]Shiao YJ, et al., Acteoside and Isoacteoside Protect Amyloid β Peptide Induced Cytotoxicity, Cognitive Deficit and Neurochemical Disturbances In Vitro and In Vivo. Int J Mol Sci. 2017 Apr 24;18 (4) :895.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Isoacteoside

Isoacteoside is a hydroxycinnamic acid.

CAS Number61303-13-7
PubChem CID6476333
IUPAC Name[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular FormulaC29H36O15
Molecular Weight624.6
XLogP-0.5
Topological Polar Surface Area245
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count15
Rotatable Bond Count11
Heavy Atom Count44
Formal Charge0
Complexity936
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O
InChI
InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
InChIKey
FNMHEHXNBNCPCI-QEOJJFGVSA-N
Chemical Structure
2D Structure
2D structure of Isoacteoside
CAS: 61303-13-7
CID: 6476333
Formula: C29H36O15
MW: 624.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight624.6
XLogP3-0.5
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count15
Rotatable Bond Count11
Exact Mass624.20542044
Monoisotopic Mass624.20542044
Topological Polar Surface Area245 Ų
Heavy Atom Count44
Formal Charge0
Complexity936
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BUP06480-01Isoacteoside
A12071-25Isoacteoside 25mg
A12071-5Isoacteoside 5mg
CS-T-103707Isoacteoside-13C3
AR-V05978-01Isoacteoside (Isoverbascoside)
A12071-100Isoacteoside 100mg
A12071-50Isoacteoside 50mg
A12071-10Isoacteoside 10mg

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