(3S,5R)-5-(Toluene-4-sulfonylamino)-piperidine-3-carboxylic Acid [9-(4-Methoxy-butyl)-9H-xanthen-9-ylmethyl]-amide

ID: ALA2322207

Chembl Id: CHEMBL2322207

PubChem CID: 11963435

Max Phase: Preclinical

Molecular Formula: C32H39N3O5S

Molecular Weight: 577.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCCCC1(CNC(=O)[C@@H]2CNC[C@H](NS(=O)(=O)c3ccc(C)cc3)C2)c2ccccc2Oc2ccccc21

Standard InChI:  InChI=1S/C32H39N3O5S/c1-23-13-15-26(16-14-23)41(37,38)35-25-19-24(20-33-21-25)31(36)34-22-32(17-7-8-18-39-2)27-9-3-5-11-29(27)40-30-12-6-4-10-28(30)32/h3-6,9-16,24-25,33,35H,7-8,17-22H2,1-2H3,(H,34,36)/t24-,25+/m0/s1

Standard InChI Key:  LBPUIWQYAGTBDC-LOSJGSFVSA-N

Alternative Forms

1. Parent:

   

   ALA2322207

   (3s,5r)-N-{[9-(4-Methoxybutyl)-9h-Xanthen-9-Yl]methyl}-5-{[(4-Methylphenyl)sulfonyl]amino}piperidine-3-Carboxamide

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: 577.75

Molecular Weight (Monoisotopic): 577.2610

AlogP: 4.28

#Rotatable Bonds: 11

Polar Surface Area: 105.76

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.39

CX Basic pKa: 8.35

CX LogP: 4.17

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.29

Np Likeness Score: -0.57

References

1. Ostermann N, Ruedisser S, Ehrhardt C, Breitenstein W, Marzinzik A, Jacoby E, Vangrevelinghe E, Ottl J, Klumpp M, Hartwieg JC, Cumin F, Hassiepen U, Trappe J, Sedrani R, Geisse S, Gerhartz B, Richert P, Francotte E, Wagner T, Krömer M, Kosaka T, Webb RL, Rigel DF, Maibaum J, Baeschlin DK..  (2013)  A novel class of oral direct renin inhibitors: highly potent 3,5-disubstituted piperidines bearing a tricyclic p3-p1 pharmacophore.,  56  (6): [PMID:23360239] [10.1021/jm301706j]

2. Ostermann N, Ruedisser S, Ehrhardt C, Breitenstein W, Marzinzik A, Jacoby E, Vangrevelinghe E, Ottl J, Klumpp M, Hartwieg JC, Cumin F, Hassiepen U, Trappe J, Sedrani R, Geisse S, Gerhartz B, Richert P, Francotte E, Wagner T, Krömer M, Kosaka T, Webb RL, Rigel DF, Maibaum J, Baeschlin DK..  (2013)  A novel class of oral direct renin inhibitors: highly potent 3,5-disubstituted piperidines bearing a tricyclic p3-p1 pharmacophore.,  56  (6): [PMID:23360239] [10.1021/jm301706j]

Source

Source(1):

• Scientific Literature