1-(4-Methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide

ID: ALA3990145

Chembl Id: CHEMBL3990145

Cas Number: 1202265-63-1

PubChem CID: 44554894

Max Phase: Phase

Molecular Formula: C27H41N5O4

Molecular Weight: 499.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(2): Imarikiren hydrochloride | Tak-272

Canonical SMILES:  COCCCCn1c(C(=O)N(CC(C)C)[C@@H]2CNC[C@H](C(=O)N3CCOCC3)C2)nc2ccccc21

Standard InChI:  InChI=1S/C27H41N5O4/c1-20(2)19-32(22-16-21(17-28-18-22)26(33)30-11-14-36-15-12-30)27(34)25-29-23-8-4-5-9-24(23)31(25)10-6-7-13-35-3/h4-5,8-9,20-22,28H,6-7,10-19H2,1-3H3/t21-,22+/m1/s1

Standard InChI Key:  RHIBAIKQWJNESW-YADHBBJMSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA3990145

   1H-Benzimidazole-2-carboxamide, 1-(4-methoxybutyl)-N-(2-methylpropyl)-N-((3S,5R)-5-(4-morpholinylcarbonyl)-3-piperidinyl)-, hydrochloride (1:1)

2. Parent:

   

   ALA3990145

   IMARIKIREN

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 499.66

Molecular Weight (Monoisotopic): 499.3159

AlogP: 2.40

#Rotatable Bonds: 10

Polar Surface Area: 88.93

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.85

CX LogP: 1.84

CX LogD: 0.38

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.51

Np Likeness Score: -1.42

References

1. Tokuhara H, Imaeda Y, Fukase Y, Iwanaga K, Taya N, Watanabe K, Kanagawa R, Matsuda K, Kajimoto Y, Kusumoto K, Kondo M, Snell G, Behnke CA, Kuroita T..  (2018)  Discovery of benzimidazole derivatives as orally active renin inhibitors: Optimization of 3,5-disubstituted piperidine to improve pharmacokinetic profile.,  26  (12): [PMID:29754833] [10.1016/j.bmc.2018.04.051]

Source

Source(1):

• Scientific Literature