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  3. 2-[2-hydroxy-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]phenyl]acetic acid

SCS-C005963

2-[2-hydroxy-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]phenyl]acetic acid

Pathway: Terpenoids Superclass: Meroterpenoids Class: Merosesquiterpenoids
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Chemical Structure

Structure of 2-[2-hydroxy-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]phenyl]acetic 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
370.5 Da
Threshold ≤ 500
ALogP
6.37
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C24H34O3
Molecular Weight:
370.5330 Da
SMILES:
CC(C)=CCC/C(C)=C/CC/C(C)=C/CCc1ccc(O)c(CC(=O)O)c1
InChIKey:
NJKADXLXQQMKCK-FIOGTWENSA-N
InChI:
InChI=1S/C24H34O3/c1-18(2)8-5-9-19(3)10-6-11-20(4)12-7-13-21-14-15-23(25)22(16-21)17-24(26)27/h8,10,12,14-16,25H,5-7,9,11,13,17H2,1-4H3,(H,26,27)/b19-10+,20-12+
Calculated Properties
ALogP:
6.371 lipophilicity
TPSA:
57.53 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
2
Rotatable Bonds:
11
Ring Count:
1 (1 aromatic)
Chiral Centers:
0
Fsp³:
0.4583 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005963
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Merosesquiterpenoids
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 14.0 μM 10.3390/md12074096 Marine Drugs
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Structure enlarged