3-(4-Hydroxyimino-2-pyrrolo[1,2-c]pyrimidin-3-yl-4H-chromen-6-yloxy)-azetidine-1-carboxylic Acid Dimethylamide

ID: ALA4100586

PubChem CID: 137661688

Max Phase: Preclinical

Molecular Formula: C22H21N5O4

Molecular Weight: 419.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)C(=O)N1CC(Oc2ccc3oc(-c4cc5cccn5cn4)c/c(=N\O)c3c2)C1

Standard InChI:  InChI=1S/C22H21N5O4/c1-25(2)22(28)27-11-16(12-27)30-15-5-6-20-17(9-15)18(24-29)10-21(31-20)19-8-14-4-3-7-26(14)13-23-19/h3-10,13,16,29H,11-12H2,1-2H3/b24-18+

Standard InChI Key:  DGCDCXGDNVBQOY-HKOYGPOVSA-N

Molfile:  

     RDKit          2D

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    7.0355   -5.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0344   -6.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424   -6.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7406   -4.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4492   -5.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4481   -6.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1581   -6.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1605   -4.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8752   -5.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8765   -6.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1606   -3.9574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8683   -3.5488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5943   -7.2405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3082   -7.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2937   -6.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0056   -6.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0159   -7.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027   -7.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2788   -6.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7861   -6.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277   -4.7836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201   -5.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307   -4.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194   -5.7718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088   -5.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9118   -6.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2040   -5.7721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9120   -6.9977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2038   -4.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -6.1809    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
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  7 10  1  0
  9  8  1  0
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  8 11  2  0
 11 12  1  0
 10 13  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
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  1 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 23  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100586

   ---

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: 419.44

Molecular Weight (Monoisotopic): 419.1594

AlogP: 2.78

#Rotatable Bonds: 3

Polar Surface Area: 95.81

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.39

CX Basic pKa: 0.60

CX LogP: 0.89

CX LogD: 0.59

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -0.76

References

1. Charvin D, Pomel V, Ortiz M, Frauli M, Scheffler S, Steinberg E, Baron L, Deshons L, Rudigier R, Thiarc D, Morice C, Manteau B, Mayer S, Graham D, Giethlen B, Brugger N, Hédou G, Conquet F, Schann S..  (2017)  Discovery, Structure-Activity Relationship, and Antiparkinsonian Effect of a Potent and Brain-Penetrant Chemical Series of Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4.,  60  (20): [PMID:28902994] [10.1021/acs.jmedchem.7b00991]

Source

Source(1):

• Scientific Literature