(3R,5S)-5-((4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)thieno[3,2-d]pyrimidin-6-yl)ethynyl)pyrrolidin-3-yl pyrrolidine-1-carboxylate

ID: ALA451513

PubChem CID: 25263270

Max Phase: Preclinical

Molecular Formula: C30H27ClFN5O3S

Molecular Weight: 592.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1CN[C@H](C#Cc2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3s2)C1)N1CCCC1

Standard InChI:  InChI=1S/C30H27ClFN5O3S/c31-25-14-22(7-9-27(25)39-17-19-4-3-5-20(32)12-19)36-29-28-26(34-18-35-29)15-24(41-28)8-6-21-13-23(16-33-21)40-30(38)37-10-1-2-11-37/h3-5,7,9,12,14-15,18,21,23,33H,1-2,10-11,13,16-17H2,(H,34,35,36)/t21-,23-/m1/s1

Standard InChI Key:  UWADRORTXGMUIP-FYYLOGMGSA-N

Molfile:  

     RDKit          2D

 41 46  0  0  0  0  0  0  0  0999 V2000
   -3.4727  -27.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851  -27.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080  -26.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009  -25.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824  -26.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830  -26.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556  -25.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9053  -26.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5785  -25.5900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9818  -26.8885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592  -26.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659  -26.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508  -27.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508  -25.9176    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355  -26.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329  -26.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436  -27.4077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572  -26.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557  -26.1711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445  -25.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434  -24.9378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573  -24.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6701  -24.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836  -24.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829  -23.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6628  -23.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523  -23.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984  -24.9378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0963  -23.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119  -23.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253  -23.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2380  -23.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9510  -23.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9492  -22.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2286  -22.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5186  -22.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6664  -23.6941    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5924  -24.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3801  -24.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8572  -25.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3641  -25.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0
 20 15  1  0
  8 10  2  0
 20 21  1  0
  5  1  1  0
 21 22  1  0
  6 11  3  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 12 13  2  0
 25 26  1  0
  3  6  1  1
 26 27  2  0
 27 22  1  0
 24 28  1  0
 13 16  1  0
 25 29  1  0
 15 14  1  0
 29 30  1  0
 14 12  1  0
 30 31  1  0
  5  7  1  6
 31 32  2  0
  2  3  1  0
 32 33  1  0
 15 16  2  0
 33 34  2  0
  7  8  1  0
 34 35  1  0
 16 17  1  0
 35 36  2  0
 36 31  1  0
  3  4  1  0
 33 37  1  0
  9 38  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA451513

   (3R,5S)-5-{2-[4-({3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)thieno[3,2-d]pyrimidin-6-yl]ethynyl}pyrrolidin-3-yl pyrrolidine-1-carboxylate

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: 592.10

Molecular Weight (Monoisotopic): 591.1507

AlogP: 6.12

#Rotatable Bonds: 6

Polar Surface Area: 88.61

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.25

CX LogP: 6.10

CX LogD: 5.20

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.26

Np Likeness Score: -1.15

References

1. Stevens KL, Alligood KJ, Alberti JG, Caferro TR, Chamberlain SD, Dickerson SH, Dickson HD, Emerson HK, Griffin RJ, Hubbard RD, Keith BR, Mullin RJ, Petrov KG, Gerding RM, Reno MJ, Rheault TR, Rusnak DW, Sammond DM, Smith SC, Uehling DE, Waterson AG, Wood ER..  (2009)  Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors.,  19  (1): [PMID:19028424] [10.1016/j.bmcl.2008.11.023]

Source

Source(1):

• Scientific Literature