2-((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

ID: ALA4638680

PubChem CID: 156012728

Max Phase: Preclinical

Molecular Formula: C13H14ClFN6O2

Molecular Weight: 340.75

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]1(CC#N)[C@H](F)[C@H](n2cnc3c(N)nc(Cl)nc32)O[C@@H]1CO

Standard InChI:  InChI=1S/C13H14ClFN6O2/c1-13(2-3-16)6(4-22)23-11(8(13)15)21-5-18-7-9(17)19-12(14)20-10(7)21/h5-6,8,11,22H,2,4H2,1H3,(H2,17,19,20)/t6-,8-,11-,13-/m1/s1

Standard InChI Key:  IDWNUBYMECZIHY-VHQAPHLWSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   34.7182   -6.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9329   -5.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1387   -5.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7583   -5.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0126   -4.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3497   -4.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6868   -4.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2420   -6.2252    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.9239   -6.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1326   -6.7741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7943   -4.5271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9060   -4.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8756   -3.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0543   -3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1271   -4.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4611   -5.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5452   -5.8186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2948   -6.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9610   -5.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8735   -4.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3806   -6.9726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.2935   -5.0743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5378   -4.3738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  4  8  1  1
  1  9  1  0
  9 10  3  0
  5 11  1  1
  7 12  1  1
 11 16  1  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 12 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4638680

   ---

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: 340.75

Molecular Weight (Monoisotopic): 340.0851

AlogP: 1.21

#Rotatable Bonds: 3

Polar Surface Area: 122.87

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.20

CX LogP: 0.55

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 0.49

References

1. Labbé MO, Collins L, Lefebvre CA, Maharsy W, Beauregard J, Dostie S, Prévost M, Nemer M, Guindon Y..  (2020)  Identification of a C3'-nitrile nucleoside analogue inhibitor of pancreatic cancer cell line growth.,  30  (6): [PMID:32019711] [10.1016/j.bmcl.2020.126983]

Source

Source(1):

• Scientific Literature