SCS-C007164

eupenicisirenin B

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Cyclobisabolane sesquiterpenoids

Chemical Structure

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Source Information

Penicillium sp. SCSIO 41410 (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea

DOI: 10.1016/j.ejmech.2023.116068 · European Journal of Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

196.2 Da

Threshold ≤ 500

ALogP

1.13

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C10H12O4

Molecular Weight:

196.2020 Da

SMILES:

CC1(C(=O)O)C2C=C(C(=O)O)CCC21

InChIKey:

                        KAEHGURFOWYTCN-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C10H12O4/c1-10(9(13)14)6-3-2-5(8(11)12)4-7(6)10/h4,6-7H,2-3H2,1H3,(H,11,12)(H,13,14)

Calculated Properties

ALogP:

1.128 lipophilicity

TPSA:

74.60 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (0 aromatic)

Chiral Centers:

Fsp³:

0.6000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007164

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesquiterpenoids

NPClassifier Class:

Cyclobisabolane sesquiterpenoids

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
Anti-inflammatory	—	LPS-induced NF-κB activation	Compounds 1, 6 and 14 were revealed with obvious NF-κB inhibitory activities at 20 μM.	10.1016/j.ejmech.2023.116068 European Journal of Medicinal Chemistry

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