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ID: ALA537666
Max Phase: Preclinical
Molecular Formula: C26H46ClN3O6
Molecular Weight: 495.66
Molecule Type: Small molecule
Associated Items:
Representations
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
Associated Targets(Human)
Renin 5251 Activities
Associated Targets(non-human)
Renin 103 Activities
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Cathepsin D 510 Activities
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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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: 0 | 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):