5,6-difluoro-N-(3-(4-methylpiperazin-1-yl)propyl)-N-((1R,3R,6R)-6-(3-(piperidin-1-ylmethyl)phenyl)bicyclo[4.1.0]heptan-3-yl)-1H-benzo[d]imidazol-2-amine

ID: ALA268385

Chembl Id: CHEMBL268385

PubChem CID: 11410594

Max Phase: Preclinical

Molecular Formula: C34H46F2N6

Molecular Weight: 576.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(CCCN(c2nc3cc(F)c(F)cc3[nH]2)[C@@H]2CC[C@]3(c4cccc(CN5CCCCC5)c4)C[C@@H]3C2)CC1

Standard InChI:  InChI=1S/C34H46F2N6/c1-39-15-17-40(18-16-39)13-6-14-42(33-37-31-21-29(35)30(36)22-32(31)38-33)28-9-10-34(23-27(34)20-28)26-8-5-7-25(19-26)24-41-11-3-2-4-12-41/h5,7-8,19,21-22,27-28H,2-4,6,9-18,20,23-24H2,1H3,(H,37,38)/t27-,28+,34+/m0/s1

Standard InChI Key:  MHCFNPUPBDQPNI-HBVNVMGMSA-N

Alternative Forms

1. Parent:

   

   ALA268385

   5,6-difluoro-N-(3-(4-methylpiperazin-1-yl)propyl)-N-((1R,3R,6R)-6-(3-(piperidin-1-ylmethyl)phenyl)bicyclo[4.1.0]heptan-3-yl)-1H-benzo[d]imidazol-2-amine

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: 576.78

Molecular Weight (Monoisotopic): 576.3752

AlogP: 5.78

#Rotatable Bonds: 9

Polar Surface Area: 41.64

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.05

CX Basic pKa: 8.99

CX LogP: 5.95

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.35

Np Likeness Score: -0.60

References

1. Sasikumar TK, Qiang L, Burnett DA, Greenlee WJ, Hawes BE, Kowalski TJ, O'Neill K, Spar BD, Weig B..  (2006)  Novel aminobenzimidazoles as selective MCH-R1 antagonists for the treatment of metabolic diseases.,  16  (20): [PMID:16889961] [10.1016/j.bmcl.2006.07.058]

2. Helal MA, Chittiboyina AG, Avery MA..  (2019)  Identification of a new small molecule chemotype of Melanin Concentrating Hormone Receptor-1 antagonists using pharmacophore-based virtual screening.,  29  (24): [PMID:31678007] [10.1016/j.bmcl.2019.126741]

Source

Source(1):

• Scientific Literature