SCS-C006323

acteoside

Pathway: Shikimates and Phenylpropanoids Superclass: Phenylethanoids (C6-C2) | Phenylpropanoids (C6-C3) Class: Cinnamic acids and derivatives | Phenylethanoids Glycoside

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Chemical Structure

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

Source Information

Avicennia marina (mangrove fruit)

Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Lamiales Family Acanthaceae Genus Avicennia Species Avicennia marina

South China Sea

DOI: 10.1007/s13659-018-0167-9 · Natural Products and Bioprospecting

Drug-likeness (Lipinski Ro5)

Molecular Weight

624.6 Da

Threshold ≤ 500

ALogP

-1.02

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C29H36O15

Molecular Weight:

624.5920 Da

SMILES:

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H](O)[C@H](O)[C@H]1O

InChIKey:

                        FBSKJMQYURKNSU-ZLSOWSIRSA-N
                        
                    

InChI:

InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1

Calculated Properties

ALogP:

-1.016 lipophilicity

TPSA:

245.29 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (2 aromatic)

Chiral Centers:

Fsp³:

0.4828 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006323

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Phenylethanoids (C6-C2) Phenylpropanoids (C6-C3)

NPClassifier Class:

Cinnamic acids and derivatives Phenylethanoids

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.

Activity	Assay	Target / model	Result	Reference
Antioxidant	DPPH free radical scavenging	DPPH free radical	compounds 4, 5, 8, 18–23, 27, 28 showed potent scavenging activities with IC50 values from 0.36 to 13.07 μg/mL	10.1007/s13659-018-0167-9 Natural Products and Bioprospecting

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