SCS-C005843
ent-3,4-seco-17-oxo-kaur-4(19),15(16)-dien-3-oic acid
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Secokaurane diterpenoids
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
Excoecaria agallocha
(mangrove plant)
Original source name: Excoecaria agallocha L.
Kingdom
Viridiplantae
Phylum
Streptophyta
Class
Magnoliopsida
Order
Malpighiales
Family
Euphorbiaceae
Genus
Excoecaria
Species
Excoecaria agallocha
Wenchang
DOI:
10.6023/cjoc202404024
· Chinese Journal of Organic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
316.4 Da
Threshold ≤ 500
ALogP
4.39
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H28O3
Molecular Weight:
316.4410 Da
SMILES:
C=C(C)[C@H]1CC[C@]23C=C(C=O)[C@H](CC[C@H]2[C@]1(C)CCC(=O)O)C3
InChIKey:
AVMDINWQUHLKEA-YTYFBAJQSA-N
InChI:
InChI=1S/C20H28O3/c1-13(2)16-6-9-20-10-14(15(11-20)12-21)4-5-17(20)19(16,3)8-7-18(22)23/h11-12,14,16-17H,1,4-10H2,2-3H3,(H,22,23)/t14-,16-,17+,19-,20+/m1/s1
Calculated Properties
ALogP:
4.385 lipophilicity
TPSA:
54.37 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
5
Ring Count:
3
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.7000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005843
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Secokaurane diterpenoids
Glycoside:
No
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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | NO production in LPS-induced BV-2 microglial cells | IC50 = (14.32±1.99) μmol/L | 10.6023/cjoc202404024 Chinese Journal of Organic Chemistry |