(R)-methyl 1-(2-(1H-indol-3-yl)-2-oxoacetyl)pyrrolidine-2-carboxylate

ID: ALA3113611

PubChem CID: 76314095

Max Phase: Preclinical

Molecular Formula: C16H16N2O4

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H]1CCCN1C(=O)C(=O)c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C16H16N2O4/c1-22-16(21)13-7-4-8-18(13)15(20)14(19)11-9-17-12-6-3-2-5-10(11)12/h2-3,5-6,9,13,17H,4,7-8H2,1H3/t13-/m1/s1

Standard InChI Key:  WRRZPBYFMHCXPZ-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   32.0724  -21.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0712  -22.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7860  -22.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7842  -21.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4995  -21.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4999  -22.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2903  -22.6071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7786  -21.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2894  -21.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6961  -20.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5211  -20.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2780  -19.8354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9393  -21.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9278  -19.8222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7473  -19.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9123  -18.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1946  -18.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5860  -19.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3050  -20.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0575  -21.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1103  -20.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6681  -20.7638    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
 16 17  1  0
 17 18  1  0
 18 14  1  0
 15 19  1  6
 19 20  2  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113611

   methyl (2R)-1-[2-(1H-indol-3-yl)-2-oxoacetyl]pyrrolidine-2-carboxylate

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: 300.31

Molecular Weight (Monoisotopic): 300.1110

AlogP: 1.51

#Rotatable Bonds: 3

Polar Surface Area: 79.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: ┄

CX LogP: 1.47

CX LogD: 1.47

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: -0.54

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