SCS-C006161

(±)-phenylbutyrolactone IIa

Pathway: Shikimates and Phenylpropanoids Superclass: Diazotetronic acids and derivatives Class: Pulvinones

Chemical Structure

Structure of (±)-phenylbutyrolactone IIa

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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

Aspergillus spelaeus (NA)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus spelaeus

South China Sea · 21.573° N, 109.767° E

DOI: 10.3390/md23060251 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

310.3 Da

Threshold ≤ 500

ALogP

2.58

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C18H14O5

Molecular Weight:

310.3050 Da

SMILES:

O=C1OC(Cc2ccccc2)(C(=O)O)C(c2ccccc2)=C1O

InChIKey:

                        UQPIVTIDGLWPHY-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C18H14O5/c19-15-14(13-9-5-2-6-10-13)18(17(21)22,23-16(15)20)11-12-7-3-1-4-8-12/h1-10,19H,11H2,(H,21,22)

Calculated Properties

ALogP:

2.579 lipophilicity

TPSA:

83.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.1111 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006161

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Diazotetronic acids and derivatives

NPClassifier Class:

Pulvinones

Glycoside:

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	inhibition rate	phosphodiesterase 4 (PDE4)	compounds 2, 3, 5, 8, 9, 11–14, and 16 exhibited weak PDE4 inhibitory activity at a concentration of 10 μM	10.3390/md23060251 Marine Drugs

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