(R)-dimethyl 2-(2-(1H-indol-3-yl)-2-oxoacetamido)pentanedioate

ID: ALA3113610

PubChem CID: 76317665

Max Phase: Preclinical

Molecular Formula: C17H18N2O6

Molecular Weight: 346.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N2O6/c1-24-14(20)8-7-13(17(23)25-2)19-16(22)15(21)11-9-18-12-6-4-3-5-10(11)12/h3-6,9,13,18H,7-8H2,1-2H3,(H,19,22)/t13-/m1/s1

Standard InChI Key:  WQQBTNYLUGEZRL-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

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   24.4146  -22.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4134  -22.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1282  -23.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1265  -21.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8418  -22.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8420  -22.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6325  -23.2240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1208  -22.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6317  -21.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0384  -21.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8633  -21.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6202  -20.4523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2816  -21.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2701  -20.4390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0950  -20.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5018  -19.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5133  -21.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1064  -21.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3382  -21.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7564  -21.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0836  -19.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4904  -18.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3163  -18.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0731  -17.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7370  -18.9858    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  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113610

   dimethyl (2R)-2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]pentanedioate

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: 346.34

Molecular Weight (Monoisotopic): 346.1165

AlogP: 0.96

#Rotatable Bonds: 7

Polar Surface Area: 114.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: ┄

CX LogP: 0.99

CX LogD: 0.99

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: -0.09

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