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

ID: ALA3102954

PubChem CID: 72792897

Max Phase: Preclinical

Molecular Formula: C19H14N2O4

Molecular Weight: 334.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(O)c(-c2cnc3[nH]cc(-c4ccc(O)c(O)c4)c3c2)c1

Standard InChI:  InChI=1S/C19H14N2O4/c22-12-2-4-16(23)13(7-12)11-5-14-15(9-21-19(14)20-8-11)10-1-3-17(24)18(25)6-10/h1-9,22-25H,(H,20,21)

Standard InChI Key:  BIAXUZOPKUTHPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.8772  -11.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761  -12.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907  -12.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889  -10.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627  -10.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3044  -11.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046  -12.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949  -12.3448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832  -11.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945  -11.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4824  -10.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3075  -10.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6957   -9.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2594   -8.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4308   -8.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0464   -9.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660  -10.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4523   -9.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371  -10.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400  -10.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542  -11.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6468   -8.0918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572  -12.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5202   -9.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525   -8.7858    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
 14 22  1  0
 21 23  1  0
 13 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102954

   4-[5-(2,5-dihydroxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]benzene-1,2-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: 334.33

Molecular Weight (Monoisotopic): 334.0954

AlogP: 3.72

#Rotatable Bonds: 2

Polar Surface Area: 109.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.92

CX Basic pKa: 2.82

CX LogP: 3.30

CX LogD: 3.29

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: 0.49

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