(S)-(2-(3-Fluorophenyl)-1-((6-(p-tolyl)thieno[2,3-d]-pyrimidin-4-yl)amino)ethyl)phosphonic Acid

ID: ALA4534214

PubChem CID: 155546879

Max Phase: Preclinical

Molecular Formula: C21H19FN3O3PS

Molecular Weight: 443.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cc3c(N[C@H](Cc4cccc(F)c4)P(=O)(O)O)ncnc3s2)cc1

Standard InChI:  InChI=1S/C21H19FN3O3PS/c1-13-5-7-15(8-6-13)18-11-17-20(23-12-24-21(17)30-18)25-19(29(26,27)28)10-14-3-2-4-16(22)9-14/h2-9,11-12,19H,10H2,1H3,(H,23,24,25)(H2,26,27,28)/t19-/m0/s1

Standard InChI Key:  ASWGUDOBPNZODI-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    2.4378  -17.3137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366  -18.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1488  -18.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8626  -18.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1470  -16.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570  -17.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675  -16.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324  -16.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3173  -16.1033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423  -15.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647  -15.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7738  -14.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657  -13.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401  -13.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1306  -14.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739  -13.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5758  -18.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863  -18.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9994  -18.5426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7058  -18.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021  -19.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026  -18.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2836  -17.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9900  -16.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6952  -17.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4011  -16.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3988  -16.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6848  -15.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819  -16.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793  -14.8614    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 13 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  2  0
 18 23  1  6
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534214

   ---

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: 443.44

Molecular Weight (Monoisotopic): 443.0869

AlogP: 4.96

#Rotatable Bonds: 6

Polar Surface Area: 95.34

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.43

CX Basic pKa: 3.92

CX LogP: 2.09

CX LogD: 1.93

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.36

References

1. Feng Y, Park J, Li SG, Boutin R, Viereck P, Schilling MA, Berghuis AM, Tsantrizos YS..  (2019)  Chirality-Driven Mode of Binding of α-Aminophosphonic Acid-Based Allosteric Inhibitors of the Human Farnesyl Pyrophosphate Synthase (hFPPS).,  62  (21): [PMID:31577901] [10.1021/acs.jmedchem.9b01104]

Source

Source(1):

• Scientific Literature