SCS-C001586

Asterriquinone B4

Pathway: Alkaloids Superclass: Tryptophan alkaloids Class: Carbazole alkaloids

Chemical Structure

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Download: SDF SMILES

Source Information

Aspergillus terreus LM.5.2 (mangrove endophytic fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus terreus

Khanh Hoa Province

DOI: 10.3390/md18120608 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

534.7 Da

Threshold ≤ 500

ALogP

7.14

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C34H34N2O4

Molecular Weight:

534.6560 Da

SMILES:

C=CC(C)(C)c1[nH]c2ccccc2c1C1=C(OC)C(=O)C(c2c(C(C)(C)C=C)[nH]c3ccccc23)=C(OC)C1=O

InChIKey:

                        WPGTVFRLUUSKCP-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C34H34N2O4/c1-9-33(3,4)31-23(19-15-11-13-17-21(19)35-31)25-27(37)30(40-8)26(28(38)29(25)39-7)24-20-16-12-14-18-22(20)36-32(24)34(5,6)10-2/h9-18,35-36H,1-2H2,3-8H3

Calculated Properties

ALogP:

7.143 lipophilicity

TPSA:

84.18 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (4 aromatic)

Chiral Centers:

Fsp³:

0.2353 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001586

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Carbazole alkaloids

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	—	Neuro-2a cells	91.45 μM	10.3390/md18120608 Marine Drugs
Neuroprotective / Neuromodulatory	—	reactive oxygen species (ROS)	36.3 %	10.3390/md18120608 Marine Drugs

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