SCS-C008004
hippolide A
Pathway: Terpenoids
Superclass: Sesterterpenoids
Class: Linear sesterterpenoids
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
Hippospongia lachne
(NA)
Original source name: H. lachne
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Dictyoceratida
Family
Spongiidae
Genus
Hippospongia
Species
Hippospongia lachne
South China Sea
DOI:
10.1021/np200227s
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
415.6 Da
Threshold ≤ 500
ALogP
4.88
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C25H37NO4
Molecular Weight:
415.5740 Da
SMILES:
CC(C)=CCC/C(C)=C/CC/C(C)=C/CCC1=CC[C@H]([C@@H]2CC(=O)NC2=O)O[C@@H]1O
InChIKey:
DHMXAXCAWHUFET-HVFQXGRFSA-N
InChI:
InChI=1S/C25H37NO4/c1-17(2)8-5-9-18(3)10-6-11-19(4)12-7-13-20-14-15-22(30-25(20)29)21-16-23(27)26-24(21)28/h8,10,12,14,21-22,25,29H,5-7,9,11,13,15-16H2,1-4H3,(H,26,27,28)/b18-10+,19-12+/t21-,22+,25-/m0/s1
Calculated Properties
ALogP:
4.882 lipophilicity
TPSA:
75.63 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
10
Ring Count:
2
(0 aromatic)
Chiral Centers:
3
Fsp³:
0.6000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008004
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Linear sesterterpenoids
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 |
|---|---|---|---|---|
| Antitumor | IC50 | A549 human lung epithelial cell line | 0.0522 μM | 10.1021/np200227s Journal of Natural Products |
| Antitumor | IC50 | HeLa human cervical carcinoma cell line | 0.048 μM | 10.1021/np200227s Journal of Natural Products |
| Antitumor | IC50 | HCT-116 human colon cancer cell line | 9.78 μM | 10.1021/np200227s Journal of Natural Products |
| Enzyme inhibition | IC50 | protein tyrosine phosphatase 1B (PTP1B) | 23.81 μM | 10.1021/np200227s Journal of Natural Products |
| Anti-inflammatory | IC50 | protein kinase C γ (PKCγ) | 61.97 μM | 10.1021/np200227s Journal of Natural Products |