(2R,3R,4S,5R)-2-(4-amino-5-(cyclopropylethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA4560390

PubChem CID: 155558648

Max Phase: Preclinical

Molecular Formula: C16H18N4O4

Molecular Weight: 330.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(C#CC1CC1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H18N4O4/c17-14-11-9(4-3-8-1-2-8)5-20(15(11)19-7-18-14)16-13(23)12(22)10(6-21)24-16/h5,7-8,10,12-13,16,21-23H,1-2,6H2,(H2,17,18,19)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  JDFHLPSWOYWYEA-XNIJJKJLSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   20.0903  -19.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8243  -20.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8617  -19.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8716  -18.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0936  -18.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3031  -20.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6066  -18.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0504  -20.5204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8227  -21.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0471  -21.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5762  -18.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5596  -19.6535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2741  -18.4414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2708  -19.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1302  -20.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5795  -17.2166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0742  -22.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3834  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5054  -22.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8454  -17.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5956  -16.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3474  -15.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5166  -15.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7380  -15.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  1  0
 12  3  1  0
 13 14  1  0
 14 12  2  0
  6 15  1  6
 16 11  1  0
  9 17  1  6
 10 18  1  1
 19 18  1  0
  4  5  1  0
  9 10  1  0
 13 11  2  0
  5 20  1  0
 20 21  3  0
 21 22  1  0
 23 22  1  0
 24 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560390

   ---

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: 330.34

Molecular Weight (Monoisotopic): 330.1328

AlogP: -0.61

#Rotatable Bonds: 2

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 4.92

CX LogP: -0.02

CX LogD: -0.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 0.90

References

1. Spurr SS, Bayle ED, Yu W, Li F, Tempel W, Vedadi M, Schapira M, Fish PV..  (2016)  New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms.,  26  (18): [PMID:27485386] [10.1016/j.bmcl.2016.07.041]

Source

Source(1):

• Scientific Literature