(2R,4S,5S,7S)-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-amino-N-(3-amino-3-oxopropyl)-4-hydroxy-2,8-dimethylnonanamide hydrochloride

ID: ALA537666

Chembl Id: CHEMBL537666

PubChem CID: 23626421

Max Phase: Preclinical

Molecular Formula: C26H46ClN3O6

Molecular Weight: 495.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCCOc1cc(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C)C(=O)NCCC(N)=O)C(C)C)ccc1OC.Cl

Standard InChI:  InChI=1S/C26H45N3O6.ClH/c1-17(2)20(14-19-7-8-23(34-5)24(15-19)35-12-6-11-33-4)16-21(27)22(30)13-18(3)26(32)29-10-9-25(28)31;/h7-8,15,17-18,20-22,30H,6,9-14,16,27H2,1-5H3,(H2,28,31)(H,29,32);1H/t18-,20+,21+,22+;/m1./s1

Standard InChI Key:  XDDTZGCWCZBADK-RKBSWOHJSA-N

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: 495.66

Molecular Weight (Monoisotopic): 495.3308

AlogP: 2.02

#Rotatable Bonds: 18

Polar Surface Area: 146.13

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 1.29

CX LogD: -0.83

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: 0.16

References

1. Göschke R, Stutz S, Rasetti V, Cohen NC, Rahuel J, Rigollier P, Baum HP, Forgiarini P, Schnell CR, Wagner T, Gruetter MG, Fuhrer W, Schilling W, Cumin F, Wood JM, Maibaum J..  (2007)  Novel 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamide transition state peptidomimetics are potent and orally active inhibitors of human renin.,  50  (20): [PMID:17824679] [10.1021/jm070314y]

2. Maibaum J, Stutz S, Göschke R, Rigollier P, Yamaguchi Y, Cumin F, Rahuel J, Baum HP, Cohen NC, Schnell CR, Fuhrer W, Gruetter MG, Schilling W, Wood JM..  (2007)  Structural modification of the P2' position of 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamides: the discovery of aliskiren, a potent nonpeptide human renin inhibitor active after once daily dosing in marmosets.,  50  (20): [PMID:17824680] [10.1021/jm070316i]

Source

Source(1):

• Scientific Literature