SCS-C005816

penilarane C

Pathway: Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids

Chemical Structure

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Download: SDF SMILES

Source Information

Penicillium sp. F0836 (soft coral-derived fungus)

Original source name: Penicillium sp. (strain F0836)

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

South China Sea · -670m · 115.1896°E, 20.0887°N

DOI: 10.1021/acs.jmedchem.5c03055 · Journal of Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

478.9 Da

Threshold ≤ 500

ALogP

1.73

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H27ClO8

Molecular Weight:

478.9250 Da

SMILES:

C[C@H]1O[C@@H]2OC(=O)[C@]3(CO)C[C@@H]4[C@@]5(C)C(=C1O[C@H]5C=C1C(=CC(=O)OC1(C)C)[C@@]4(O)CCl)[C@H]23

InChIKey:

                        YLPYFVVOEBMUKY-AWVAJRJJSA-N
                        
                    

InChI:

InChI=1S/C24H27ClO8/c1-10-18-16-17-19(30-10)32-20(28)23(17,9-26)7-13-22(16,4)14(31-18)5-11-12(24(13,29)8-25)6-15(27)33-21(11,2)3/h5-6,10,13-14,17,19,26,29H,7-9H2,1-4H3/t10-,13-,14+,17-,19-,22-,23+,24+/m1/s1

Calculated Properties

ALogP:

1.734 lipophilicity

TPSA:

111.52 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005816

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Tetraketide 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
Receptor / Signaling modulation	inhibition	TGF-β1/Smad signaling	10.0 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry
Antifibrotic / Organ protection	IC50	HSF1/AMPK metabolic axis	1.5 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry

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