2-(4-Amino-5-phenyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-phenyl-ethanol

ID: ALA471945

PubChem CID: 44565856

Max Phase: Preclinical

Molecular Formula: C20H18N4O

Molecular Weight: 330.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccccc1)cn2[C@@H](CO)c1ccccc1

Standard InChI:  InChI=1S/C20H18N4O/c21-19-18-16(14-7-3-1-4-8-14)11-24(20(18)23-13-22-19)17(12-25)15-9-5-2-6-10-15/h1-11,13,17,25H,12H2,(H2,21,22,23)/t17-/m0/s1

Standard InChI Key:  VWFOFGYBQLNHQS-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.2286   -6.2955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -7.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -7.5348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -5.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978   -6.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983   -7.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -7.3785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764   -6.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -6.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -5.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010   -4.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -3.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9392   -3.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888   -4.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235   -5.0590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437   -8.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -8.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499   -8.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -9.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1093   -9.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -8.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -7.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5975   -7.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136   -8.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  9 10  1  0
  5  4  2  0
  4 16  1  0
  6  7  1  0
  7 17  1  0
  7  8  1  0
 17 18  1  6
  8  9  2  0
 17 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 21 22  2  0
 10 11  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 11 12  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA471945

   (2R)-2-(4-amino-5-phenylpyrrolo[2,3-d]pyrimidin-7-yl)-2-phenylethanol

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: 330.39

Molecular Weight (Monoisotopic): 330.1481

AlogP: 3.26

#Rotatable Bonds: 4

Polar Surface Area: 76.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.03

CX LogP: 3.25

CX LogD: 3.23

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -0.42

References

1. Widler L, Green J, Missbach M, Susa M, Altmann E..  (2001)  7-Alkyl- and 7-cycloalkyl-5-aryl-pyrrolo[2,3-d]pyrimidines--potent inhibitors of the tyrosine kinase c-Src.,  11  (6): [PMID:11277535] [10.1016/s0960-894x(01)00079-8]

2. Tintori C, Magnani M, Schenone S, Botta M..  (2009)  Docking, 3D-QSAR studies and in silico ADME prediction on c-Src tyrosine kinase inhibitors.,  44  (3): [PMID:18722033] [10.1016/j.ejmech.2008.07.002]

Source

Source(1):

• Scientific Literature