SCS-C005840

chrysogenolide H

Pathway: Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids

Chemical Structure

Loading 3D structure...

3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

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

3.04

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@]1(C)O[C@H]2OC(=O)[C@@H]3[C@H]2[C@@](C)(C[C@H]2C(C)=C4CC(=O)OC(C)(C)C4=CC[C@]32C)C1=O

InChIKey:

                        ZZHZJRNCLIOQGM-LWDXKWSNSA-N
                        
                    

InChI:

InChI=1S/C26H32O8/c1-12-13-10-16(27)33-23(2,3)14(13)8-9-24(4)15(12)11-25(5)18-17(24)19(28)32-20(18)34-26(6,21(25)29)22(30)31-7/h8,15,17-18,20H,9-11H2,1-7H3/t15-,17-,18+,20+,24-,25+,26+/m0/s1

Calculated Properties

ALogP:

3.037 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-C005840

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

Back to Compounds