SCS-C005835

peniciacetal E

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

488.6 Da

Threshold ≤ 500

ALogP

3.53

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H36O8

Molecular Weight:

488.5770 Da

SMILES:

C=C(C)C1=CC[C@]2(C)[C@@H]3C(=O)O[C@@H]4O[C@](C)(C(=O)OC)C(=O)[C@](C)(C[C@H]2[C@]1(C)CCC(=O)OC)[C@@H]43

InChIKey:

                        ZCEOJSYLSCJWMR-DJNBASMJSA-N
                        
                    

InChI:

InChI=1S/C27H36O8/c1-14(2)15-9-11-25(4)16(24(15,3)12-10-17(28)32-7)13-26(5)19-18(25)20(29)34-21(19)35-27(6,22(26)30)23(31)33-8/h9,16,18-19,21H,1,10-13H2,2-8H3/t16-,18-,19+,21+,24+,25-,26+,27-/m0/s1

Calculated Properties

ALogP:

3.531 lipophilicity

TPSA:

105.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.7037 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005835

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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