SCS-C008298
Sinuscalide A
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Cembrane diterpenoids
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.
Source Information
Sinularia scabra
(soft coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Sinulariidae
Genus
Sinularia
Species
Sinularia scabra
South China Sea
· 15 m
DOI:
10.1021/acs.joc.2c00784
· The Journal of Organic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
330.4 Da
Threshold ≤ 500
ALogP
2.15
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C19H22O5
Molecular Weight:
330.3800 Da
SMILES:
C=C(C)[C@@H]1C/C=C2/C(=O)O[C@H]3C[C@]4(C)CC(=O)[C@@H](O4)[C@@H](C(=O)C1)[C@@H]23
InChIKey:
UHWISWHSNQXZNO-DCFXEATLSA-N
InChI:
InChI=1S/C19H22O5/c1-9(2)10-4-5-11-15-14(23-18(11)22)8-19(3)7-13(21)17(24-19)16(15)12(20)6-10/h5,10,14-17H,1,4,6-8H2,2-3H3/b11-5+/t10-,14+,15+,16+,17-,19+/m1/s1
Calculated Properties
ALogP:
2.146 lipophilicity
TPSA:
69.67 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
5
Rotatable Bonds:
1
Ring Count:
4
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.6316 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008298
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Cembrane 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 |
|---|---|---|---|---|
| Antiviral | IC50 | human enterovirus EV71 | 5.0 μM | 10.1021/acs.joc.2c00784 The Journal of Organic Chemistry |
| Bone metabolism / Osteoclast | inhibition rate | RANKL-induced osteoclastogenesis | 52.3 % | 10.1021/acs.joc.2c00784 The Journal of Organic Chemistry |
| Bone metabolism / Osteoclast | IC50 | RANKL-induced osteoclastogenesis | 9.7 μM | 10.1021/acs.joc.2c00784 The Journal of Organic Chemistry |