(2R)-2-{[6-ethyl-5-(3-hydroxyphenyl)thieno[2,3-d]pyrimidin-4-yl]amino}propanoic acid

ID: ALA4521112

PubChem CID: 155542475

Max Phase: Preclinical

Molecular Formula: C17H17N3O3S

Molecular Weight: 343.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1sc2ncnc(N[C@H](C)C(=O)O)c2c1-c1cccc(O)c1

Standard InChI:  InChI=1S/C17H17N3O3S/c1-3-12-13(10-5-4-6-11(21)7-10)14-15(20-9(2)17(22)23)18-8-19-16(14)24-12/h4-9,21H,3H2,1-2H3,(H,22,23)(H,18,19,20)/t9-/m1/s1

Standard InChI Key:  ZVAJPNVZGQNWQE-SECBINFHSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.4865  -12.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4853  -13.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1934  -13.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9005  -13.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002  -12.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1916  -12.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1891  -11.2158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4802  -10.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7737  -11.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648  -10.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762  -12.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6787  -12.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1601  -12.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791  -13.5096    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9773  -12.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862  -13.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309  -11.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778   -9.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320  -11.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9843  -10.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4371   -9.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342  -10.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3856  -10.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7837  -10.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 12  5  1  0
 13 12  2  0
 14 13  1  0
  4 14  1  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
  8 18  1  1
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521112

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.41

Molecular Weight (Monoisotopic): 343.0991

AlogP: 3.51

#Rotatable Bonds: 5

Polar Surface Area: 95.34

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.57

CX Basic pKa: 3.58

CX LogP: 3.43

CX LogD: 0.93

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.78

References

1. Szlávik Z, Ondi L, Csékei M, Paczal A, Szabó ZB, Radics G, Murray J, Davidson J, Chen I, Davis B, Hubbard RE, Pedder C, Dokurno P, Surgenor A, Smith J, Robertson A, LeToumelin-Braizat G, Cauquil N, Zarka M, Demarles D, Perron-Sierra F, Claperon A, Colland F, Geneste O, Kotschy A..  (2019)  Structure-Guided Discovery of a Selective Mcl-1 Inhibitor with Cellular Activity.,  62  (15): [PMID:31339316] [10.1021/acs.jmedchem.9b00134]

Source

Source(1):

• Scientific Literature