2-Benzyl-N*1*-[1-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-N*4*-methyl-N*4*-(2-pyridin-2-yl-ethyl)-succinamide

ID: ALA343968

Chembl Id: CHEMBL343968

PubChem CID: 9987285

Max Phase: Preclinical

Molecular Formula: C39H55N5O5S

Molecular Weight: 705.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](O)[C@H](O)[C@H](CC1CCCCC1)NC(=O)[C@H](Cc1cscn1)NC(=O)[C@@H](CC(=O)N(C)CCc1ccccn1)Cc1ccccc1

Standard InChI:  InChI=1S/C39H55N5O5S/c1-27(2)20-35(45)37(47)33(22-29-14-8-5-9-15-29)42-39(49)34(24-32-25-50-26-41-32)43-38(48)30(21-28-12-6-4-7-13-28)23-36(46)44(3)19-17-31-16-10-11-18-40-31/h4,6-7,10-13,16,18,25-27,29-30,33-35,37,45,47H,5,8-9,14-15,17,19-24H2,1-3H3,(H,42,49)(H,43,48)/t30-,33+,34+,35+,37-/m1/s1

Standard InChI Key:  FTOFUXGQJCLRCU-UOXQYSJJSA-N

Alternative Forms

1. Parent:

   

   ALA343968

   (2R)-2-benzyl-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-N'-methyl-N'-(2-pyridin-2-ylethyl)butanediamide

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: 705.97

Molecular Weight (Monoisotopic): 705.3924

AlogP: 4.74

#Rotatable Bonds: 19

Polar Surface Area: 144.75

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.38

CX Basic pKa: 4.54

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 50

QED Weighted: 0.14

Np Likeness Score: -0.41

References

1. Rosenberg SH, Spina KP, Condon SL, Polakowski J, Yao Z, Kovar P, Stein HH, Cohen J, Barlow JL, Klinghofer V..  (1993)  Studies directed toward the design of orally active renin inhibitors. 2. Development of the efficacious, bioavailable renin inhibitor (2S)-2-benzyl-3- [[(1-methylpiperazin-4-yl)sulfonyl]propionyl]-3-thiazol-4-yl-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (A-72517).,  36  (4): [PMID:8474102] [10.1021/jm00056a006]

Source

Source(1):

• Scientific Literature