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  3. (1S,5R)-8-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-9-oxa-2-azabicyclo[3.3.1]nona-3,7-diene-4-carbaldehyde

SCS-C005960

(1S,5R)-8-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-9-oxa-2-azabicyclo[3.3.1]nona-3,7-diene-4-carbaldehyde

Pathway: Terpenoids Superclass: Sesterterpenoids
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Chemical Structure

Structure of (1S,5R)-8-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-9-oxa-2-azabicyclo[3.3.1]nona-3,7-diene-4-carbaldehyde
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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.
Download: SDF SMILES

Source Information

Hippospongia lachne (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Spongiidae Genus Hippospongia Species Hippospongia lachne
South China Sea
DOI: 10.3390/md12074096  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
369.5 Da
Threshold ≤ 500
ALogP
5.91
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C24H35NO2
Molecular Weight:
369.5490 Da
SMILES:
CC(C)=CCC/C(C)=C/CC/C(C)=C/CCC1=CC[C@H]2O[C@@H]1NC=C2C=O
InChIKey:
NBDXDCAGBMWVRR-XZGCBMSOSA-N
InChI:
InChI=1S/C24H35NO2/c1-18(2)8-5-9-19(3)10-6-11-20(4)12-7-13-21-14-15-23-22(17-26)16-25-24(21)27-23/h8,10,12,14,16-17,23-25H,5-7,9,11,13,15H2,1-4H3/b19-10+,20-12+/t23-,24+/m1/s1
Calculated Properties
ALogP:
5.913 lipophilicity
TPSA:
38.33 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
10
Ring Count:
2 (0 aromatic)
Chiral Centers:
2
Fsp³:
0.5417 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005960
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
N/A
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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
Enzyme inhibition IC50 PTP1B 5.2 μM 10.3390/md12074096 Marine Drugs
Antitumor IC50 HCT-116 cancer cell line 11.6 μM 10.3390/md12074096 Marine Drugs
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Structure enlarged