SCS-C000499

butyrolactone I

Pathway: Shikimates and Phenylpropanoids Superclass: Lignans Class: Neolignans

Chemical Structure

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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 terreus (mangrove endophytic fungus)

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

South China Sea

DOI: 10.1039/c8ra01840e · RSC Advances

Drug-likeness (Lipinski Ro5)

Molecular Weight

424.4 Da

Threshold ≤ 500

ALogP

3.59

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H24O7

Molecular Weight:

424.4000 Da

SMILES:

COC(=O)[C@@]1(Cc2ccc(O)c(CC=C(C)C)c2)OC(=O)C(O)=C1c1ccc(O)cc1

InChIKey:

                        NGOLMNWQNHWEKU-DEOSSOPVSA-N
                        
                    

InChI:

InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m0/s1

Calculated Properties

ALogP:

3.587 lipophilicity

TPSA:

113.29 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.2500 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000499

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Lignans

NPClassifier Class:

Neolignans

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
Antitumor	inhibition_percent	HL-60	25.3 %	10.1039/c8ra01840e RSC Advances
Antitumor	IC50	HL-60	13.22 μM	10.1039/c8ra01840e RSC Advances

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