(R)-methyl 2-(2-(1H-indol-3-yl)-2-oxoacetamido)-3-(1H-indol-3-yl)propanoate

ID: ALA3113608

PubChem CID: 7117396

Max Phase: Preclinical

Molecular Formula: C22H19N3O4

Molecular Weight: 389.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)C(=O)c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C22H19N3O4/c1-29-22(28)19(10-13-11-23-17-8-4-2-6-14(13)17)25-21(27)20(26)16-12-24-18-9-5-3-7-15(16)18/h2-9,11-12,19,23-24H,10H2,1H3,(H,25,27)/t19-/m1/s1

Standard InChI Key:  HIFDOUATSGPYEI-LJQANCHMSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    7.0149  -22.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0138  -22.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7285  -23.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7267  -21.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4422  -22.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4424  -22.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2328  -23.1112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7211  -22.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2319  -21.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6387  -21.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4636  -21.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2205  -20.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818  -21.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8703  -20.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6953  -20.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1020  -19.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1135  -21.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7067  -21.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9384  -21.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3567  -21.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9270  -19.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4121  -20.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1947  -19.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014  -18.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1904  -19.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8021  -18.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6260  -17.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8328  -17.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2245  -18.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 17 18  2  0
 17 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  2  0
 22 23  1  0
 23 25  1  0
 24 21  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113608

   methyl (2R)-3-(1H-indol-3-yl)-2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]propanoate

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: 389.41

Molecular Weight (Monoisotopic): 389.1376

AlogP: 2.73

#Rotatable Bonds: 6

Polar Surface Area: 104.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.68

CX Basic pKa: ┄

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.27

Np Likeness Score: -0.17

References

1. Prasher P, Pooja, Singh P..  (2014)  Lead modification: amino acid appended indoles as highly effective 5-LOX inhibitors.,  22  (5): [PMID:24508141] [10.1016/j.bmc.2014.01.027]

Source

Source(1):

• Scientific Literature