3-(1H-Indol-3-yl)-N-phenethyl-2-[2-(2-pyridin-3-yl-acetylamino)-propionylamino]-propionamide

ID: ALA3144500

PubChem CID: 90663967

Max Phase: Preclinical

Molecular Formula: C29H31N5O3

Molecular Weight: 497.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)Cc1cccnc1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1

Standard InChI:  InChI=1S/C29H31N5O3/c1-20(33-27(35)16-22-10-7-14-30-18-22)28(36)34-26(17-23-19-32-25-12-6-5-11-24(23)25)29(37)31-15-13-21-8-3-2-4-9-21/h2-12,14,18-20,26,32H,13,15-17H2,1H3,(H,31,37)(H,33,35)(H,34,36)/t20-,26-/m0/s1

Standard InChI Key:  NKJSFZDQEZUOJT-FNZWTVRRSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    5.6106   -8.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7540   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3049   -8.6176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0396   -6.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -8.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3251   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8975   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244   -9.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3251   -7.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830   -7.1026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7174   -9.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4685   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7540   -7.9276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -5.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8975   -5.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7553   -6.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -7.1026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6119   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3264   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1817   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0409   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0764   -9.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7553   -5.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4685   -5.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625  -10.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3264   -5.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -5.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -7.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0409   -5.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8215  -10.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145  -10.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -6.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -5.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -5.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  1  2  0
  6 10  1  1
  7  6  1  0
  8 11  1  0
  9  1  1  0
 10  1  1  0
 11 13  1  0
 12  9  2  0
 13  2  1  0
 14  2  2  0
 15  7  2  0
 16  8  2  0
 17 23  2  0
 18  7  1  0
 19  8  1  0
 20 19  1  0
 21 18  1  0
 22 28  1  0
 23 20  1  0
 24  9  1  0
 25 32  2  0
 13 26  1  6
 27 12  1  0
 28 21  1  0
 29 20  2  0
 30 22  1  0
 31 22  2  0
 32 29  1  0
 33 24  2  0
 34 33  1  0
 35 31  1  0
 36 30  2  0
 37 35  2  0
  3 12  1  0
 27 34  2  0
 37 36  1  0
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144500

   deamino-Gly(pyrid-3-yl)-Ala-Trp-NHEtPh

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: 497.60

Molecular Weight (Monoisotopic): 497.2427

AlogP: 2.70

#Rotatable Bonds: 11

Polar Surface Area: 115.98

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: 4.87

CX LogP: 2.51

CX LogD: 2.50

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: -0.67

References

1. Weber D, Berger C, Eickelmann P, Antel J, Kessler H..  (2003)  Design of selective peptidomimetic agonists for the human orphan receptor BRS-3.,  46  (10): [PMID:12723954] [10.1021/jm0210921]

Source

Source(1):

• Scientific Literature