SCS-C001685

2'-acetoxy-7-chlorocitreorosein

Pathway: Polyketides Superclass: Polycyclic aromatic polyketides Class: Anthraquinones and anthrones

Chemical Structure

Structure of 2'-acetoxy-7-chlorocitreorosein

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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 citrinum HL-5126 (NA)

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

South China Sea

DOI: 10.1038/ja.2017.52 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

376.7 Da

Threshold ≤ 500

ALogP

2.60

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C18H13ClO7

Molecular Weight:

376.7000 Da

SMILES:

COc1c(Cl)c(O)cc2c1C(=O)c1c(O)cc(COC(C)=O)cc1C2=O

InChIKey:

                        OWTNKMFURYLDCW-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C18H13ClO7/c1-7(20)26-6-8-3-9-13(11(21)4-8)17(24)14-10(16(9)23)5-12(22)15(19)18(14)25-2/h3-5,21-22H,6H2,1-2H3

Calculated Properties

ALogP:

2.598 lipophilicity

TPSA:

110.13 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.1667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001685

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Polycyclic aromatic polyketides

NPClassifier Class:

Anthraquinones and anthrones

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
Antibacterial	MIC	Vibrio parahaemolyticus	10.0 μM	10.1038/ja.2017.52 The Journal of Antibiotics
Antibacterial	MIC	Staphylococcus aureus	22.8 μM	10.1038/ja.2017.52 The Journal of Antibiotics

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