SCS-C005829

chrysogenolide B

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

502.5 Da

Threshold ≤ 500

ALogP

1.24

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C26H30O10

Molecular Weight:

502.5160 Da

SMILES:

COC(=O)[C@]12C(=O)[C@@H](C)O[C@@H]3OC(=O)[C@](C)(C[C@H]4[C@]5(CO5)C5=CC(=O)OC(C)(C)[C@]56O[C@@H]6C[C@@]41C)[C@@H]32

InChIKey:

                        KXRODMCMGHNDAX-NMXLUNLASA-N
                        
                    

InChI:

InChI=1S/C26H30O10/c1-11-17(28)25(20(30)31-6)16-18(33-11)34-19(29)22(16,4)8-13-23(25,5)9-14-26(35-14)12(24(13)10-32-24)7-15(27)36-21(26,2)3/h7,11,13-14,16,18H,8-10H2,1-6H3/t11-,13-,14-,16-,18-,22-,23+,24+,25+,26+/m1/s1

Calculated Properties

ALogP:

1.237 lipophilicity

TPSA:

130.26 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.7692 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005829

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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