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  3. (3aR,4R,7aS)-4-hydroxy-2-oxo-7-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4,5,7a-tetrahydro-1H-indole-3a-carboxylic acid

SCS-C005962

(3aR,4R,7aS)-4-hydroxy-2-oxo-7-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4,5,7a-tetrahydro-1H-indole-3a-carboxylic acid

Pathway: Terpenoids Superclass: Sesterterpenoids Class: Linear sesterterpenoids
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Chemical Structure

Structure of (3aR,4R,7aS)-4-hydroxy-2-oxo-7-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4,5,7a-tetrahydro-1H-indole-3a-carboxylic acid
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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
415.6 Da
Threshold ≤ 500
ALogP
4.84
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
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](O)[C@@]2(C(=O)O)CC(=O)N[C@@H]12
InChIKey:
VHNPWMQYDSVFFH-NRPNEHDJSA-N
InChI:
InChI=1S/C25H37NO4/c1-17(2)8-5-9-18(3)10-6-11-19(4)12-7-13-20-14-15-21(27)25(24(29)30)16-22(28)26-23(20)25/h8,10,12,14,21,23,27H,5-7,9,11,13,15-16H2,1-4H3,(H,26,28)(H,29,30)/b18-10+,19-12+/t21-,23+,25+/m1/s1
Calculated Properties
ALogP:
4.836 lipophilicity
TPSA:
86.63 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
10
Ring Count:
2 (0 aromatic)
Chiral Centers:
3
Fsp³:
0.6000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005962
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Linear sesterterpenoids
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 33.0 μM 10.3390/md12074096 Marine Drugs
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Structure enlarged