SCS-C006812

dichlorochromopyrrolic acid

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

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Chemical Structure

Structure of dichlorochromopyrrolic 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

454.3 Da

Threshold ≤ 500

ALogP

6.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C22H13Cl2N3O4

Molecular Weight:

454.2690 Da

SMILES:

O=C(O)c1[nH]c(C(=O)O)c(-c2c[nH]c3ccc(Cl)cc23)c1-c1c[nH]c2ccc(Cl)cc12

InChIKey:

                        XLDGSKVUWQVTCC-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C22H13Cl2N3O4/c23-9-1-3-15-11(5-9)13(7-25-15)17-18(20(22(30)31)27-19(17)21(28)29)14-8-26-16-4-2-10(24)6-12(14)16/h1-8,25-27H,(H,28,29)(H,30,31)

Calculated Properties

ALogP:

6.014 lipophilicity

TPSA:

121.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (5 aromatic)

Chiral Centers:

Fsp³:

0.0000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006812

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	> 50.0 μM	10.1038/s41429-020-0307-4 The Journal of Antibiotics

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