SCS-C005822

penilarane I

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

494.6 Da

Threshold ≤ 500

ALogP

2.72

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H38O9

Molecular Weight:

494.5810 Da

SMILES:

COC(=O)[C@@]1(C)O[C@H]2OC(=O)[C@@H]3[C@H]2[C@@](C)(C[C@@H]2[C@]3(C)CC[C@H](C(C)(C)O)[C@@]2(C)CCC(=O)O)C1=O

InChIKey:

                        PMNXJDYEPGXIGV-AGIHTEQFSA-N
                        
                    

InChI:

InChI=1S/C26H38O9/c1-22(2,32)13-8-10-24(4)14(23(13,3)11-9-15(27)28)12-25(5)17-16(24)18(29)34-19(17)35-26(6,20(25)30)21(31)33-7/h13-14,16-17,19,32H,8-12H2,1-7H3,(H,27,28)/t13-,14+,16+,17-,19-,23-,24+,25-,26+/m1/s1

Calculated Properties

ALogP:

2.717 lipophilicity

TPSA:

136.43 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.8462 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005822

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; HSF1/AMPK metabolic axis	10.0 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry

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