SCS-C008242

lupinacidin B

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

Chemical Structure

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Source Information

Micromonospora sp. SCSIO 07396 (NA)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Micromonosporales Family Micromonosporaceae Genus Micromonospora Species NA

South China Sea

DOI: 10.1021/acs.jnatprod.6c00037 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

326.3 Da

Threshold ≤ 500

ALogP

3.23

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C19H18O5

Molecular Weight:

326.3480 Da

SMILES:

CCCCc1c(O)c(C)c(O)c2c1C(=O)c1c(O)cccc1C2=O

InChIKey:

                        IVQKRDHUECCAJE-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C19H18O5/c1-3-4-6-11-14-15(17(22)9(2)16(11)21)18(23)10-7-5-8-12(20)13(10)19(14)24/h5,7-8,20-22H,3-4,6H2,1-2H3

Calculated Properties

ALogP:

3.230 lipophilicity

TPSA:

94.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.2632 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008242

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
Antitumor	—	PANC-1, TE-1, HL60, A549, MDA-MB-231, and GSC0722	the cytotoxicity of 1–10 was evaluated against six human tumor cell lines (PANC-1, TE-1, HL60, A549, MDA-MB-231, and GSC0722); only 8 was cytotoxic against the GSC0722 cancer cell line	10.1021/acs.jnatprod.6c00037 Journal of Natural Products

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