(RSR)1-[2-(1-Carboxy-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid

ID: ALA3351100

PubChem CID: 118719308

Max Phase: Preclinical

Molecular Formula: C22H30N2O5

Molecular Weight: 402.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@H](CCc1ccccc1)C(=O)O)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21

Standard InChI:  InChI=1S/C22H30N2O5/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29)/t14-,16-,17+,18-,19-/m0/s1

Standard InChI Key:  AHYHTSYNOHNUSH-UJCHZGTJSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    9.0310   -4.3296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   -4.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3103   -4.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1110   -3.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -4.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5571   -5.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6011   -3.5060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9174   -3.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6011   -4.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8862   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8862   -3.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3103   -5.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9966   -6.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -1.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -3.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1291   -6.0397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6011   -1.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4621   -3.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7528   -3.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5505   -2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1748   -2.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8862   -4.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -3.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7528   -4.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8079   -2.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6257   -1.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -4.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3173   -3.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3173   -4.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3103   -3.7119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7125   -3.1114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4836   -5.0674    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  2  1  0
  7  9  1  0
  8  4  1  0
  9  3  1  0
 11 10  1  6
 11  7  1  0
 12  3  2  0
 13  6  2  0
 14 10  2  0
 15 11  1  0
 16  6  1  0
 17 10  1  0
 18 15  1  0
 19 18  1  0
 20  4  1  0
 21  8  1  0
  9 22  1  6
 23 19  2  0
 24 19  1  0
 25 20  1  0
 26 25  1  0
 27 24  2  0
 28 23  1  0
 29 27  1  0
  4 30  1  6
  8 31  1  6
  2 32  1  6
  5  8  1  0
 21 26  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3351100

   ---

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: 402.49

Molecular Weight (Monoisotopic): 402.2155

AlogP: 2.29

#Rotatable Bonds: 8

Polar Surface Area: 106.94

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.13

CX Basic pKa: 8.04

CX LogP: 0.19

CX LogD: -2.74

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: 0.26

References

1. Blankley CJ, Kaltenbronn JS, DeJohn DE, Werner A, Bennett LR, Bobowski G, Krolls U, Johnson DR, Pearlman WM, Hoefle ML..  (1987)  Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids.,  30  (6): [PMID:3035180] [10.1021/jm00389a006]

2. Blankley CJ, Kaltenbronn JS, DeJohn DE, Werner A, Bennett LR, Bobowski G, Krolls U, Johnson DR, Pearlman WM, Hoefle ML..  (1987)  Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids.,  30  (6): [PMID:3035180] [10.1021/jm00389a006]

3. Blankley CJ, Kaltenbronn JS, DeJohn DE, Werner A, Bennett LR, Bobowski G, Krolls U, Johnson DR, Pearlman WM, Hoefle ML..  (1987)  Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids.,  30  (6): [PMID:3035180] [10.1021/jm00389a006]

Source

Source(1):

• Scientific Literature