SCS-C000055
Gemmacolide N
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Briarane 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
Dichotella gemmacea
(gorgonian)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Scleralcyonacea
Family
Ellisellidae
Genus
Dichotella
Species
Dichotella gemmacea
Beihai
DOI:
10.3390/md9081403
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
594.6 Da
Threshold ≤ 500
ALogP
0.94
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
13
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C29H38O13
Molecular Weight:
594.6000 Da
SMILES:
COCC1=C/[C@@H]2OC(=O)[C@H](C)[C@@]2(O)[C@@H](OC(C)=O)[C@H]2[C@@]3(CO3)[C@H](OC(C)=O)C[C@H](OC(C)=O)[C@]2(C)[C@@H](OC(C)=O)/C=C\1
InChIKey:
ZVQHPUKDVWXVOI-VDPAHHKISA-N
InChI:
InChI=1S/C29H38O13/c1-14-26(34)42-23-10-19(12-36-7)8-9-20(38-15(2)30)27(6)21(39-16(3)31)11-22(40-17(4)32)28(13-37-28)24(27)25(29(14,23)35)41-18(5)33/h8-10,14,20-25,35H,11-13H2,1-7H3/b9-8-,19-10+/t14-,20-,21-,22+,23-,24+,25-,27-,28+,29-/m0/s1
Calculated Properties
ALogP:
0.944 lipophilicity
TPSA:
173.49 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
13
Rotatable Bonds:
6
Ring Count:
4
(0 aromatic)
Chiral Centers:
10
Fsp³:
0.6897 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000055
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Briarane 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 |
|---|---|---|---|---|
| Antitumor | — | A549 | > 50.5 μM | 10.3390/md9081403 Marine Drugs |
| Antitumor | — | MG63 | > 50.5 μM | 10.3390/md9081403 Marine Drugs |
| Antifungal | — | Septoria tritici | 7.5 mm | 10.3390/md9081403 Marine Drugs |
| Antibacterial | — | Escherichia coli | 12.5 mm | 10.3390/md9081403 Marine Drugs |