N-((1-(4-Chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methyl)-adamantan-2-amine

ID: ALA3798496

Chembl Id: CHEMBL3798496

PubChem CID: 127046392

Max Phase: Preclinical

Molecular Formula: C23H29ClN2

Molecular Weight: 368.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CNC2C3CC4CC(C3)CC2C4)c(C)n1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C23H29ClN2/c1-14-7-20(15(2)26(14)22-5-3-21(24)4-6-22)13-25-23-18-9-16-8-17(11-18)12-19(23)10-16/h3-7,16-19,23,25H,8-13H2,1-2H3

Standard InChI Key:  VTLQWWSMIYMOCU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3798496

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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: 368.95

Molecular Weight (Monoisotopic): 368.2019

AlogP: 5.66

#Rotatable Bonds: 4

Polar Surface Area: 16.96

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 10.07

CX LogP: 5.67

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.31

References

1. Bhakta S, Scalacci N, Maitra A, Brown AK, Dasugari S, Evangelopoulos D, McHugh TD, Mortazavi PN, Twist A, Petricci E, Manetti F, Castagnolo D..  (2016)  Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N'-((E)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria.,  59  (6): [PMID:26907951] [10.1021/acs.jmedchem.6b00031]

2. Masci D, Hind C, Islam MK, Toscani A, Clifford M, Coluccia A, Conforti I, Touitou M, Memdouh S, Wei X, La Regina G, Silvestri R, Sutton JM, Castagnolo D..  (2019)  Switching on the activity of 1,5-diaryl-pyrrole derivatives against drug-resistant ESKAPE bacteria: Structure-activity relationships and mode of action studies.,  178  [PMID:31202995] [10.1016/j.ejmech.2019.05.087]

Source

Source(1):

• Scientific Literature