SCS-C008005
hippolide B
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
429.6 Da
Threshold ≤ 500
ALogP
5.54
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C26H39NO4
Molecular Weight:
429.6010 Da
SMILES:
CO[C@H]1O[C@@H]([C@@H]2CC(=O)NC2=O)CC=C1CC/C=C(\C)CC/C=C(\C)CCC=C(C)C
InChIKey:
JCZZVHJOSFEULF-UTNVMCOPSA-N
InChI:
InChI=1S/C26H39NO4/c1-18(2)9-6-10-19(3)11-7-12-20(4)13-8-14-21-15-16-23(31-26(21)30-5)22-17-24(28)27-25(22)29/h9,11,13,15,22-23,26H,6-8,10,12,14,16-17H2,1-5H3,(H,27,28,29)/b19-11+,20-13+/t22-,23+,26-/m0/s1
Calculated Properties
ALogP:
5.536 lipophilicity
TPSA:
64.63 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
11
Ring Count:
2
(0 aromatic)
Chiral Centers:
3
Fsp³:
0.6154 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008005
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 | HCT-116 human colon cancer cell line | 35.13 μM | 10.1021/np200227s Journal of Natural Products |
| Enzyme inhibition | IC50 | protein tyrosine phosphatase 1B (PTP1B) | 39.67 μM | 10.1021/np200227s Journal of Natural Products |