2-(2-((1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-5-bromo-1H-indole

ID: ALA2172435

PubChem CID: 71460757

Max Phase: Preclinical

Molecular Formula: C18H14BrN3O

Molecular Weight: 368.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(c2cc3cc(Br)ccc3[nH]2)=N/C1=C\c1ccc[nH]1

Standard InChI:  InChI=1S/C18H14BrN3O/c1-23-18-10-16(22-17(18)9-13-3-2-6-20-13)15-8-11-7-12(19)4-5-14(11)21-15/h2-10,20-21H,1H3/b17-9-

Standard InChI Key:  WPWHOLNDAGSQAT-MFOYZWKCSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   12.3620  -17.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5749  -18.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3986  -18.1848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6951  -17.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0544  -16.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4934  -17.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0771  -17.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0982  -16.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8348  -15.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9439  -18.5977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6798  -18.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2646  -18.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8900  -17.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0566  -18.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2314  -18.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2696  -19.5847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5764  -20.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383  -19.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1691  -19.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0369  -20.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6799  -21.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4466  -20.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2648  -20.9118    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  4  6  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  7  2  0
 14 15  2  0
 15 18  1  0
 17 16  1  0
 16 14  1  0
  2 14  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2172435

   (2Z)-5-bromo-2-[(5Z)-4-methoxy-5-(1H-pyrrol-2-ylmethylidene)pyrrol-2-ylidene]indole

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: 368.23

Molecular Weight (Monoisotopic): 367.0320

AlogP: 4.63

#Rotatable Bonds: 3

Polar Surface Area: 53.17

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.88

CX Basic pKa: 3.92

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -0.45

References

1. Su JC, Chen KF, Chen WL, Liu CY, Huang JW, Tai WT, Chen PJ, Kim I, Shiau CW..  (2012)  Synthesis and biological activity of obatoclax derivatives as novel and potent SHP-1 agonists.,  56  [PMID:22982119] [10.1016/j.ejmech.2012.08.024]

Source

Source(1):

• Scientific Literature