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

ID: ALA511124

PubChem CID: 44565857

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-/m1/s1

Standard InChI Key:  VWFOFGYBQLNHQS-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.8426   -6.5382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412   -7.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535   -7.7774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515   -6.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2690   -6.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2695   -7.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0597   -7.6211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5476   -6.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0588   -6.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3105   -5.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1179   -5.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3722   -4.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8200   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0104   -4.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7600   -4.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5477   -5.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3149   -8.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638   -9.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1211   -8.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3751   -9.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1805   -9.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7325   -8.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4735   -8.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6687   -7.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -8.8467    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  1
  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:

   

   ALA511124

   (2S)-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