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  3. 3-(5-chloro-1H-indol-3-yl)-4-(5,6-dichloro-1H-indol-3-yl)-1H-pyrrole-2-carboxylic acid

SCS-C006811

3-(5-chloro-1H-indol-3-yl)-4-(5,6-dichloro-1H-indol-3-yl)-1H-pyrrole-2-carboxylic acid

Pathway: Alkaloids Superclass: Proline alkaloids Class: Pyrrole alkaloids
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Chemical Structure

Structure of 3-(5-chloro-1H-indol-3-yl)-4-(5,6-dichloro-1H-indol-3-yl)-1H-pyrrole-2-carboxylic 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
444.7 Da
Threshold ≤ 500
ALogP
6.97
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
1
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C21H12Cl3N3O2
Molecular Weight:
444.7050 Da
SMILES:
O=C(O)c1[nH]cc(-c2c[nH]c3cc(Cl)c(Cl)cc23)c1-c1c[nH]c2ccc(Cl)cc12
InChIKey:
PDJSBFURBNDNGX-UHFFFAOYSA-N
InChI:
InChI=1S/C21H12Cl3N3O2/c22-9-1-2-17-10(3-9)13(7-25-17)19-14(8-27-20(19)21(28)29)12-6-26-18-5-16(24)15(23)4-11(12)18/h1-8,25-27H,(H,28,29)
Calculated Properties
ALogP:
6.970 lipophilicity
TPSA:
84.67 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
1
Rotatable Bonds:
3
Ring Count:
5 (5 aromatic)
Chiral Centers:
0
Fsp³:
0.0000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006811
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Proline alkaloids
NPClassifier Class:
Pyrrole alkaloids
Glycoside:
No
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 13.8 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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Structure enlarged