SCS-C001309

chermesinone B

Pathway: Polyketides | Shikimates and Phenylpropanoids Superclass: Chromanes | Lignans | Flavonoids Class: Azaphilones | Flavonolignans

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Chemical Structure

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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. SCSIO 41030 (soft coral-derived fungus)

Original source name: Penicillium sp. SCSIO41030

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea · -1509m

DOI: 10.1039/d4ob00586d · Organic & Biomolecular Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

316.3 Da

Threshold ≤ 500

ALogP

2.48

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C18H20O5

Molecular Weight:

316.3000 Da

SMILES:

CC[C@H](C)C(=O)[C@H]1C(=O)O[C@@]2(C)C(=O)C=C3C=C(C)OC=C3[C@H]12

InChIKey:

                        MZMGICPQNSXAGE-SRSSHDMCSA-N
                        
                    

InChI:

InChI=1S/C18H20O5/c1-5-9(2)16(20)14-15-12-8-22-10(3)6-11(12)7-13(19)18(15,4)23-17(14)21/h6-9,14-15H,5H2,1-4H3/t9-,14-,15+,18-/m0/s1

Calculated Properties

ALogP:

2.477 lipophilicity

TPSA:

69.67 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001309

NPClassifier Pathway:

Polyketides Shikimates and Phenylpropanoids

NPClassifier Superclass:

Chromanes Lignans Flavonoids

NPClassifier Class:

Azaphilones Flavonolignans

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
Neuroprotective / Neuromodulatory	—	Primary cultured cortical neurons	10.0 μM	10.1039/d4ob00593d Organic & Biomolecular Chemistry
Neuroprotective / Neuromodulatory	—	Aβ25-35-induced neurotoxicity	1.0 μM	10.1039/d4ob00593d Organic & Biomolecular Chemistry

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