SCS-C005830

peniciacetal H

Pathway: Polyketides | 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

472.5 Da

Threshold ≤ 500

ALogP

3.18

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H32O8

Molecular Weight:

472.5340 Da

SMILES:

COC(=O)[C@]12C(=O)[C@@H](C)O[C@@H]3OC(=O)[C@](C)(CC4=C(C)C5=C(CC[C@@]41C)C(C)(C)OC(=O)C5)[C@@H]32

InChIKey:

                        UCGHGXVMMGERHZ-NDGCROJMSA-N
                        
                    

InChI:

InChI=1S/C26H32O8/c1-12-14-10-17(27)34-23(3,4)15(14)8-9-25(6)16(12)11-24(5)18-20(33-21(24)29)32-13(2)19(28)26(18,25)22(30)31-7/h13,18,20H,8-11H2,1-7H3/t13-,18-,20-,24-,25+,26+/m1/s1

Calculated Properties

ALogP:

3.181 lipophilicity

TPSA:

105.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.6923 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005830

NPClassifier Pathway:

Polyketides 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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