Acteoside

Acteoside
Compound Structure:
Synonyms: Acteoside;Verbascoside;Kusaginin;acetoside; 2R,3R,4R,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
Compound ID: NMPC-555
PubChem ID:

5281800

Molecular Formula: C29H36O15
Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
InChIKey: FBSKJMQYURKNSU-ZLSOWSIRSA-N
About the compound:

Verbascoside and acteoside are both phenylethanoid glycosides present in a variety of plants. Here are some key characteristics of each compound:

Verbascoside:

It is categorized as a caffeoyl phenylethanoid glycoside.

The structure of verbascoside comprises caffeic acid, a phenylpropanoid, forming an ester bond, and hydroxytyrosol, a phenylethanoid, forming an ether bond to the rhamnose portion of a disaccharide.

The disaccharide portion of verbascoside is β-(3',4'-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

It functions as a plant metabolite.

Acteoside:

Acteoside is a glycoside of hydroxytyrosol.

It is composed of alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol.

The hydroxy group at position 4 of the glucopyranosyl moiety undergoes esterification through formal condensation with trans-caffeic acid.

Acteoside serves various roles, including as a neuroprotective agent, antileishmanial agent, anti-inflammatory agent, and antibacterial agent.

It is classified as a cinnamate ester, a disaccharide derivative, and a member of catechols and polyphenols.

Clinical Trial:

Acteoside is currently being investigated in clinical trial NCT02662283, which focuses on evaluating the efficacy and safety of reh-acteoside therapy for patients with IgA nephropathy.


Properties:

Chemical and Physical Properties

Computed Properties

Property Name

Property Value

Molecular Weight

624.6 g/mol

XLogP3-AA

-0.5

Hydrogen Bond Donor Count

9

Hydrogen Bond Acceptor Count

15

Rotatable Bond Count

11

Exact Mass

624.20542044 g/mol

Monoisotopic Mass

624.20542044 g/mol

Topological Polar Surface Area

245Ų

Heavy Atom Count

44

Formal Charge

0

Complexity

936

Isotope Atom Count

0

Defined Atom Stereocenter Count

10

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem

Source Species: Landolphia owariensis
Macaranga barteri
Download SDF