SCS-C005838

chrysogenolide G

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

440.5 Da

Threshold ≤ 500

ALogP

2.82

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C25H28O7

Molecular Weight:

440.4920 Da

SMILES:

CC1=C2CC(=O)OC(C)(C)C2=CC[C@@]2(C)[C@H]1C[C@@]1(C)C(=O)[C@]3(C)O[C@H]4OC(=O)[C@@]2(C3=O)[C@H]41

InChIKey:

                        WMJMZLGVIAIFFR-BMSBYHRTSA-N
                        
                    

InChI:

InChI=1S/C25H28O7/c1-11-12-9-15(26)31-21(2,3)13(12)7-8-23(5)14(11)10-22(4)16-17-30-20(29)25(16,23)19(28)24(6,32-17)18(22)27/h7,14,16-17H,8-10H2,1-6H3/t14-,16+,17+,22+,23-,24-,25-/m0/s1

Calculated Properties

ALogP:

2.817 lipophilicity

TPSA:

95.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.6800 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005838

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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