5-(7-hydroxy-4-methyl-2-oxo-2H-chromen-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

ID: ALA3975572

PubChem CID: 134151742

Max Phase: Preclinical

Molecular Formula: C16H12N2O3

Molecular Weight: 280.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(=O)oc2cc(O)c(-c3ccc(C#N)n3C)cc12

Standard InChI:  InChI=1S/C16H12N2O3/c1-9-5-16(20)21-15-7-14(19)12(6-11(9)15)13-4-3-10(8-17)18(13)2/h3-7,19H,1-2H3

Standard InChI Key:  SBSAZAWOVDYWIT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    3.7791  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780  -18.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860  -18.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4842  -17.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929  -17.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1962  -18.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9086  -18.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6222  -18.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6188  -17.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018  -17.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3310  -18.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758  -17.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899  -16.3615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908  -16.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823  -16.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294  -17.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584  -15.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299  -14.6980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8974  -16.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719  -18.8103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972  -15.8147    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
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
  1 12  1  0
 14 17  1  0
 17 18  3  0
 10 19  1  0
  2 20  1  0
 13 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3975572

   ---

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: 280.28

Molecular Weight (Monoisotopic): 280.0848

AlogP: 2.68

#Rotatable Bonds: 1

Polar Surface Area: 79.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.99

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 1.88

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.04

References

1. Kinoshita M, Negishi M, Sakai H, Hirano T, Mori S, Fujii S, Kagechika H, Tanatani A..  (2016)  Development of 6-arylcoumarins as nonsteroidal progesterone antagonists. Structure-activity relationships and fluorescence properties.,  24  (21): [PMID:27665178] [10.1016/j.bmc.2016.09.020]

Source

Source(1):

• Scientific Literature