SCS-C006808

6-OMe-7',7''-dichorochromopyrrolic acid

Pathway: Alkaloids Superclass: Proline alkaloids | Tryptophan alkaloids Class: Pyrrole alkaloids | Simple indole alkaloids

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Chemical Structure

Structure of 6-OMe-7',7''-dichorochromopyrrolic acid

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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

Streptomyces sp. SCSIO 11791 (bacterium)

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

South China Sea · 1,765 m

DOI: 10.1038/s41429-020-0307-4 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

468.3 Da

Threshold ≤ 500

ALogP

6.10

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C23H15Cl2N3O4

Molecular Weight:

468.2960 Da

SMILES:

COC(=O)c1[nH]c(C(=O)O)c(-c2c[nH]c3c(Cl)cccc23)c1-c1c[nH]c2c(Cl)cccc12

InChIKey:

                        ZBGSWESTHKFXNU-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C23H15Cl2N3O4/c1-32-23(31)21-17(13-9-27-19-11(13)5-3-7-15(19)25)16(20(28-21)22(29)30)12-8-26-18-10(12)4-2-6-14(18)24/h2-9,26-28H,1H3,(H,29,30)

Calculated Properties

ALogP:

6.103 lipophilicity

TPSA:

110.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (5 aromatic)

Chiral Centers:

Fsp³:

0.0435 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006808

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Proline alkaloids Tryptophan alkaloids

NPClassifier Class:

Pyrrole alkaloids Simple indole 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	MDA-MB-435 human breast cancer cells	19.4 μM	10.1038/s41429-020-0307-4 The Journal of Antibiotics
Antitumor	IC50	MDA-MB-231, NCI-H460, HCT-116, HepG2, noncancerous MCF10A	2.2–30.4 μM	10.1038/s41429-020-0307-4 The Journal of Antibiotics

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