2-Benzylamino-N-[2-(1H-indol-3-yl)-1-phenethylcarbamoyl-ethyl]-propionamide

ID: ALA3144495

PubChem CID: 90663962

Max Phase: Preclinical

Molecular Formula: C29H32N4O2

Molecular Weight: 468.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1

Standard InChI:  InChI=1S/C29H32N4O2/c1-21(31-19-23-12-6-3-7-13-23)28(34)33-27(18-24-20-32-26-15-9-8-14-25(24)26)29(35)30-17-16-22-10-4-2-5-11-22/h2-15,20-21,27,31-32H,16-19H2,1H3,(H,30,35)(H,33,34)/t21-,27-/m0/s1

Standard InChI Key:  DBFWHAOBJXLIKL-IDISGSTGSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
    5.4226   -9.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -7.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9419  -10.8008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9627   -8.0120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2355  -10.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525   -8.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124   -7.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446   -9.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825   -8.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655  -10.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3129   -6.2969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -6.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0428   -7.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8023   -7.7001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825   -6.7647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1230   -6.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424   -6.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3931   -5.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423   -8.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3842  -10.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124   -5.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5829   -7.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2032   -5.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8530   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424   -3.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -4.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5610   -8.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8819   -9.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7221   -4.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4732   -4.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1230   -3.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8023   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -3.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9332   -3.8024    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  9  1  1
  7  6  1  0
  8  1  1  0
  9  1  1  0
 10  8  2  0
 11 13  1  0
 12  2  2  0
 13  2  1  0
 14  7  2  0
 15  7  1  0
 16 11  1  0
 17 15  1  0
 18 16  1  0
 19 22  1  0
 20  8  1  0
 21 10  1  0
 22 17  1  0
 13 23  1  1
 24 18  2  0
 25 18  1  0
 26 19  2  0
 27 19  1  0
 28 20  2  0
 29 28  1  0
 30 27  2  0
 31 24  1  0
 32 25  2  0
 33 26  1  0
 34 30  1  0
 35 32  1  0
  3 10  1  0
 21 29  2  0
 33 34  2  0
 31 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144495

   (2S)-2-[[(2S)-2-(benzylamino)propanoyl]amino]-3-(1H-indol-3-yl)-N-(2-phenylethyl)propanamide

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: 468.60

Molecular Weight (Monoisotopic): 468.2525

AlogP: 3.73

#Rotatable Bonds: 11

Polar Surface Area: 86.02

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: 7.75

CX LogP: 4.23

CX LogD: 3.72

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -0.49

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