SCS-C006324
calceolarioside A
Pathway: Shikimates and Phenylpropanoids
Superclass: Phenylethanoids (C6-C2) | Phenylpropanoids (C6-C3)
Class: Cinnamic acids and derivatives | Phenylethanoids
Glycoside
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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
478.4 Da
Threshold ≤ 500
ALogP
0.13
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
2 violations (HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C23H26O11
Molecular Weight:
478.4500 Da
SMILES:
O=C(/C=C/c1ccc(O)c(O)c1)O[C@H]1[C@H](O)[C@@H](O)[C@H](OCCc2ccc(O)c(O)c2)O[C@@H]1CO
InChIKey:
UHIGZYLCYRQESL-VJWFJHQPSA-N
InChI:
InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1
Calculated Properties
ALogP:
0.132 lipophilicity
TPSA:
186.37 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
11
Rotatable Bonds:
8
Ring Count:
3
(2 aromatic)
Chiral Centers:
5
Fsp³:
0.3478 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006324
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
Natural product databases
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 | — Structured numeric value is not available in this record; see the primary reference. | 10.1007/s13659-018-0167-9 Natural Products and Bioprospecting |