SCS-C008412

lebstatin

Pathway: Polyketides Superclass: Macrolides Class: Ansa macrolides

Chemical Structure

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Source Information

Streptomyces sp. (bacterium)

Original source name: Streptomyces sp. SCSIO 1934

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species NA

South China Sea · 200 m · E111°26.118', N18°34.363'

Year: 2011

Drug-likeness (Lipinski Ro5)

Molecular Weight

546.7 Da

Threshold ≤ 500

ALogP

3.86

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C29H42N2O8

Molecular Weight:

546.6610 Da

SMILES:

COc1c(O)cc2cc1C[C@@H](C)C[C@@H](OC)[C@H](O)[C@@H](C)/C=C(\C)C(OC(N)=O)C(OC)/C=C\C=C(/C)C(=O)N2

InChIKey:

                        GULKMGRAQDRMKW-ALJAUKIVSA-N
                        
                    

InChI:

InChI=1S/C29H42N2O8/c1-16-11-20-14-21(15-22(32)27(20)38-7)31-28(34)17(2)9-8-10-23(36-5)26(39-29(30)35)19(4)13-18(3)25(33)24(12-16)37-6/h8-10,13-16,18,23-26,32-33H,11-12H2,1-7H3,(H2,30,35)(H,31,34)/b10-8-,17-9+,19-13+/t16-,18+,23?,24-,25-,26?/m1/s1

Calculated Properties

ALogP:

3.861 lipophilicity

TPSA:

149.57 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.5172 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008412

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Ansa macrolides

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
Antiviral	inhibition	herpes simplex virus type 1	antiviral activity; inhibition; target: herpes simplex virus type 1	—
Antitumor	inhibition	lung cancer cells	antitumor activity; inhibition; target: lung cancer cells	—

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