SCS-C005827

chrysogenolide C

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids

Chemical Structure

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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

488.5 Da

Threshold ≤ 500

ALogP

2.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H32O9

Molecular Weight:

488.5330 Da

SMILES:

COC(=O)[C@]12C(=O)[C@@H](C)O[C@@H]3OC(=O)[C@](C)(C[C@@H]4[C@]1(C)CC=C1C(=CC(=O)OC1(C)C)[C@@]4(C)O)[C@@H]32

InChIKey:

                        AVSVGIXGBAHHHO-POPOOAMJSA-N
                        
                    

InChI:

InChI=1S/C26H32O9/c1-12-18(28)26(21(30)32-7)17-19(33-12)34-20(29)23(17,4)11-15-24(26,5)9-8-13-14(25(15,6)31)10-16(27)35-22(13,2)3/h8,10,12,15,17,19,31H,9,11H2,1-7H3/t12-,15-,17-,19-,23-,24+,25-,26+/m1/s1

Calculated Properties

ALogP:

2.008 lipophilicity

TPSA:

125.43 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-C005827

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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