SCS-C007590

guignardone Z

Pathway: Terpenoids Superclass: Meroterpenoids Class: Miscellaneous meroterpenoids | Prenyl quinone meroterpenoids

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

358.5 Da

Threshold ≤ 500

ALogP

3.85

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H30O4

Molecular Weight:

358.4780 Da

SMILES:

CC(C)=CC/C=C(/C)[C@@H]1CC[C@@]2(C)OC3=C(C[C@@H]12)C(=O)[C@]1(O)CO[C@H]3C1

InChIKey:

                        JZNUQSGAGXCOFE-TZPAZIFNSA-N
                        
                    

InChI:

InChI=1S/C22H30O4/c1-13(2)6-5-7-14(3)15-8-9-21(4)17(15)10-16-19(26-21)18-11-22(24,12-25-18)20(16)23/h6-7,15,17-18,24H,5,8-12H2,1-4H3/b14-7-/t15-,17-,18-,21+,22+/m0/s1

Calculated Properties

ALogP:

3.851 lipophilicity

TPSA:

55.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.6818 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007590

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Miscellaneous meroterpenoids Prenyl quinone meroterpenoids

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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