(1-(3-Aminophenyl)-1H-pyrrol-3-yl)(3,4,5-trimethoxyphenyl)-methanone

ID: ALA3318100

Chembl Id: CHEMBL3318100

PubChem CID: 102340756

Max Phase: Preclinical

Molecular Formula: C20H20N2O4

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)c2ccn(-c3cccc(N)c3)c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H20N2O4/c1-24-17-9-14(10-18(25-2)20(17)26-3)19(23)13-7-8-22(12-13)16-6-4-5-15(21)11-16/h4-12H,21H2,1-3H3

Standard InChI Key:  RLKGRFCJEXIHGX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3318100

   [1-(3-Aminophenyl)pyrrol-3-yl]-(3,4,5-trimethoxyphenyl)methanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 352.39

Molecular Weight (Monoisotopic): 352.1423

AlogP: 3.32

#Rotatable Bonds: 6

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.39

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.54

References

1. La Regina G, Bai R, Coluccia A, Famiglini V, Pelliccia S, Passacantilli S, Mazzoccoli C, Ruggieri V, Sisinni L, Bolognesi A, Rensen WM, Miele A, Nalli M, Alfonsi R, Di Marcotullio L, Gulino A, Brancale A, Novellino E, Dondio G, Vultaggio S, Varasi M, Mercurio C, Hamel E, Lavia P, Silvestri R..  (2014)  New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer.,  57  (15): [PMID:25025991] [10.1021/jm500561a]

2. La Regina G, Bai R, Coluccia A, Famiglini V, Pelliccia S, Passacantilli S, Mazzoccoli C, Ruggieri V, Verrico A, Miele A, Monti L, Nalli M, Alfonsi R, Di Marcotullio L, Gulino A, Ricci B, Soriani A, Santoni A, Caraglia M, Porto S, Da Pozzo E, Martini C, Brancale A, Marinelli L, Novellino E, Vultaggio S, Varasi M, Mercurio C, Bigogno C, Dondio G, Hamel E, Lavia P, Silvestri R..  (2015)  New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer.,  58  (15): [PMID:26132075] [10.1021/acs.jmedchem.5b00310]

3. La Regina G, Bai R, Coluccia A, Famiglini V, Passacantilli S, Naccarato V, Ortar G, Mazzoccoli C, Ruggieri V, Agriesti F, Piccoli C, Tataranni T, Nalli M, Brancale A, Vultaggio S, Mercurio C, Varasi M, Saponaro C, Sergio S, Maffia M, Coluccia AML, Hamel E, Silvestri R..  (2017)  3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin.,  8  (5): [PMID:28523104] [10.1021/acsmedchemlett.7b00022]

Source

Source(1):

• Scientific Literature