SCS-C000566

penicillide

Pathway: Polyketides Superclass: Aromatic polyketides Class: Depsidones

Chemical Structure

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Source Information

Penicillium pinophilum (NA)

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

South China Sea

DOI: 10.1021/acs.jnatprod.5b00575 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

372.4 Da

Threshold ≤ 500

ALogP

4.25

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C21H24O6

Molecular Weight:

372.4000 Da

SMILES:

COc1c([C@@H](O)CC(C)C)ccc2c1C(=O)OCc1cc(C)cc(O)c1O2

InChIKey:

                        UOWGLBYIKHMCIS-HNNXBMFYSA-N
                        
                    

InChI:

InChI=1S/C21H24O6/c1-11(2)7-15(22)14-5-6-17-18(20(14)25-4)21(24)26-10-13-8-12(3)9-16(23)19(13)27-17/h5-6,8-9,11,15,22-23H,7,10H2,1-4H3/t15-/m0/s1

Calculated Properties

ALogP:

4.251 lipophilicity

TPSA:

85.22 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.3810 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000566

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Aromatic polyketides

NPClassifier Class:

Depsidones

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
Antifouling	EC50	Balanus amphitrite settlement	2.6 μg/mL	10.1021/acs.jnatprod.5b00575 Journal of Natural Products
Enzyme inhibition	IC50	calcium-activated papain-like protease	7.1 μM	10.1021/acs.jnatprod.5b00575 Journal of Natural Products

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