(5-Methoxy-7-acetamido-3-acetoxy-2-oxindole-3-yl)acetonitrile

ID: ALA4085946

PubChem CID: 137644063

Max Phase: Preclinical

Molecular Formula: C15H15N3O5

Molecular Weight: 317.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)=O)c2c(c1)C(CC#N)(OC(C)=O)C(=O)N2

Standard InChI:  InChI=1S/C15H15N3O5/c1-8(19)17-12-7-10(22-3)6-11-13(12)18-14(21)15(11,4-5-16)23-9(2)20/h6-7H,4H2,1-3H3,(H,17,19)(H,18,21)

Standard InChI Key:  HTXOGVHRKQZGKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   12.9378   -7.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5390   -7.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3326   -6.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9434   -9.7566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4103   -9.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2106   -9.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9442   -8.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1639   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4574   -8.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7623   -8.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7694   -9.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4758   -9.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1710   -9.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7319   -7.7599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5280   -7.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8135   -8.6528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0429   -7.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7837  -11.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7909  -11.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0814  -10.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4830  -10.7316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0558   -8.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607   -8.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  3  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  4 13  1  0
  8 13  2  0
  2  7  1  0
 15 16  2  0
 15 17  1  0
 14 15  1  0
  7 14  1  0
 18 19  1  0
 18 20  2  0
 18 21  1  0
 12 21  1  0
 22 23  1  0
 10 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085946

   ---

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: 317.30

Molecular Weight (Monoisotopic): 317.1012

AlogP: 1.28

#Rotatable Bonds: 4

Polar Surface Area: 117.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.46

CX Basic pKa: ┄

CX LogP: -0.27

CX LogD: -0.27

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: 0.19

References

1. Zaryanova EV, Lozinskaya NA, Beznos OV, Volkova MS, Chesnokova NB, Zefirov NS..  (2017)  Oxindole-based intraocular pressure reducing agents.,  27  (16): [PMID:28687205] [10.1016/j.bmcl.2017.06.065]

2. Lozinskaya NA, Babkov DA, Zaryanova EV, Bezsonova EN, Efremov AM, Tsymlyakov MD, Anikina LV, Zakharyascheva OY, Borisov AV, Perfilova VN, Tyurenkov IN, Proskurnina MV, Spasov AA..  (2019)  Synthesis and biological evaluation of 3-substituted 2-oxindole derivatives as new glycogen synthase kinase 3β inhibitors.,  27  (9): [PMID:30902399] [10.1016/j.bmc.2019.03.028]

3. Klochkov VG, Bezsonova EN, Dubar M, Melekhina DD, Temnov VV, Zaryanova EV, Lozinskaya NA, Babkov DA, Spasov AA..  (2022)  Towards multi-target antidiabetic agents: In vitro and in vivo evaluation of 3,5-disubstituted indolin-2-one derivatives as novel α-glucosidase inhibitors.,  55  [PMID:34780899] [10.1016/j.bmcl.2021.128449]

Source

Source(1):

• Scientific Literature