SCS-C000854

terrequinone A

Pathway: Alkaloids Superclass: Tryptophan alkaloids Class: Carbazole alkaloids

Chemical Structure

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Source Information

Aspergillus nidulans SD-531 (deep-sea fungus)

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

South China Sea

DOI: 10.1007/s00343-020-0052-3 · Journal of Oceanology and Limnology

Drug-likeness (Lipinski Ro5)

Molecular Weight

490.6 Da

Threshold ≤ 500

ALogP

7.34

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C32H30N2O3

Molecular Weight:

490.6000 Da

SMILES:

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

InChIKey:

                        NBSHFMWBYVHWNG-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C32H30N2O3/c1-6-32(4,5)31-26(20-12-8-10-14-24(20)34-31)27-28(35)21(16-15-18(2)3)25(29(36)30(27)37)22-17-33-23-13-9-7-11-19(22)23/h6-15,17,33-35H,1,16H2,2-5H3

Calculated Properties

ALogP:

7.344 lipophilicity

TPSA:

85.95 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (4 aromatic)

Chiral Centers:

Fsp³:

0.1875 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000854

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
Antitumor	IC50	NCI-H460; MCF-7; SF-268	5.4–13.9 μM	10.1007/s00343-020-0052-3 Journal of Oceanology and Limnology

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