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

ID: ALA4104288

PubChem CID: 137658017

Max Phase: Preclinical

Molecular Formula: C16H16N4O5

Molecular Weight: 344.33

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(NC(C)=O)c2c(c1)C(CC#N)(OC(C)=O)C(=O)N2

Standard InChI:  InChI=1S/C16H16N4O5/c1-8(21)18-11-6-12-14(13(7-11)19-9(2)22)20-15(24)16(12,4-5-17)25-10(3)23/h6-7H,4H2,1-3H3,(H,18,21)(H,19,22)(H,20,24)

Standard InChI Key:  RMLLBRMRRXMZFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   12.9587   -7.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5542   -8.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3632   -7.2053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9388  -10.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4149   -9.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2132  -10.1047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9541   -9.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1699   -9.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4690   -9.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682   -9.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682  -10.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4690  -10.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1699  -10.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7426   -8.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5410   -8.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8201   -9.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0604   -8.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682  -11.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0674  -11.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682  -12.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4690  -11.5818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3665   -9.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6657   -9.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3665  -10.3684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0674   -9.1550    0.0000 N   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
 22 24  2  0
 22 25  1  0
 10 25  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4104288

    ---

Associated Targets(non-human)

Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 344.33Molecular Weight (Monoisotopic): 344.1121AlogP: 1.23#Rotatable Bonds: 4
Polar Surface Area: 137.39Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 11.31CX Basic pKa: CX LogP: -0.88CX LogD: -0.88
Aromatic Rings: 1Heavy Atoms: 25QED Weighted: 0.70Np Likeness Score: -0.20

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]

Source