3-Phenyl-5-(2,4-dihydroxyphenyl)-1H-pyrrolo[2,3-b]pyridine

ID: ALA3102957

PubChem CID: 72792828

Max Phase: Preclinical

Molecular Formula: C19H14N2O2

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2cnc3[nH]cc(-c4ccccc4)c3c2)c(O)c1

Standard InChI:  InChI=1S/C19H14N2O2/c22-14-6-7-15(18(23)9-14)13-8-16-17(11-21-19(16)20-10-13)12-4-2-1-3-5-12/h1-11,22-23H,(H,20,21)

Standard InChI Key:  PAHLFLUAFODUJL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    6.6092  -16.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081  -17.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3226  -18.0725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208  -16.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8948  -16.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0360  -16.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0363  -17.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8265  -17.9163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3147  -17.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8260  -16.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2139  -15.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0389  -15.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4270  -15.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9909  -14.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1624  -14.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7780  -15.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8980  -15.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845  -15.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4693  -15.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723  -16.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863  -16.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545  -15.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894  -17.6574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  5  1  0
 19 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102957

   4-(3-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzene-1,3-diol

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: 302.33

Molecular Weight (Monoisotopic): 302.1055

AlogP: 4.31

#Rotatable Bonds: 2

Polar Surface Area: 69.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.00

CX Basic pKa: 2.85

CX LogP: 3.91

CX LogD: 3.90

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: 0.15

References

1. Gourdain S, Dairou J, Denhez C, Bui LC, Rodrigues-Lima F, Janel N, Delabar JM, Cariou K, Dodd RH..  (2013)  Development of DANDYs, new 3,5-diaryl-7-azaindoles demonstrating potent DYRK1A kinase inhibitory activity.,  56  (23): [PMID:24188002] [10.1021/jm401049v]

Source

Source(1):

• Scientific Literature