SCS-C007595

guignardianone A

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

Chemical Structure

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Source Information

Penicillium sp. NBUF154 (soft coral-derived fungus)

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

South China Sea · 60 m

DOI: 10.1002/cbdv.202200475 · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight

366.4 Da

Threshold ≤ 500

ALogP

3.74

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H22O5

Molecular Weight:

366.4130 Da

SMILES:

CC(C)[C@@]1(C(=O)OCCc2ccccc2)OC(=O)/C(=C/c2ccccc2)O1

InChIKey:

                        JMCOITWCCHSPBR-ZHFOUCBBSA-N
                        
                    

InChI:

InChI=1S/C22H22O5/c1-16(2)22(21(24)25-14-13-17-9-5-3-6-10-17)26-19(20(23)27-22)15-18-11-7-4-8-12-18/h3-12,15-16H,13-14H2,1-2H3/b19-15-/t22-/m0/s1

Calculated Properties

ALogP:

3.739 lipophilicity

TPSA:

61.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.2727 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007595

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
Antiviral	inhibition	human enterovirus 71 (EV71)	while other the compounds were inactive even at the highest concentrations tested (20.0 μM).	10.1002/cbdv.202200475 Chemistry & Biodiversity
Antibacterial	inhibition	ten Vibrio strains (including V. parahaemolyticus NBUV004, P. damselae NBUV007, etc.)	Compounds 1–8 were found to display no inhibition against these pathogens.	10.1002/cbdv.202200475 Chemistry & Biodiversity

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