SCS-C005821

penilarane H

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

414.5 Da

Threshold ≤ 500

ALogP

3.49

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H30O6

Molecular Weight:

414.4980 Da

SMILES:

CC1=C2CC(=O)OC(C)(C)C2=CC[C@]2(C)[C@@H]3C(=O)O[C@@H]4O[C@@H](C)C(=O)[C@](C)(C[C@@H]12)[C@@H]43

InChIKey:

                        LPEVQTYMXSHUOV-DCIKXNMPSA-N
                        
                    

InChI:

InChI=1S/C24H30O6/c1-11-13-9-16(25)30-22(3,4)14(13)7-8-23(5)15(11)10-24(6)18-17(23)20(27)29-21(18)28-12(2)19(24)26/h7,12,15,17-18,21H,8-10H2,1-6H3/t12-,15-,17-,18+,21-,23-,24+/m0/s1

Calculated Properties

ALogP:

3.494 lipophilicity

TPSA:

78.90 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.7083 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005821

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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