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

ID: ALA4525316

PubChem CID: 155543019

Max Phase: Preclinical

Molecular Formula: C14H15N5O5

Molecular Weight: 333.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ncco1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H15N5O5/c15-11-8-6(13-16-1-2-23-13)3-19(12(8)18-5-17-11)14-10(22)9(21)7(4-20)24-14/h1-3,5,7,9-10,14,20-22H,4H2,(H2,15,17,18)/t7-,9-,10-,14-/m1/s1

Standard InChI Key:  OBJFCGTXMJYNKV-AKAIJSEGSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   29.5086  -20.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2426  -21.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2800  -20.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2900  -19.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5119  -19.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7214  -22.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0249  -20.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4688  -21.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2410  -22.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4654  -22.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9945  -19.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9779  -20.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6925  -19.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6891  -20.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5485  -22.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9979  -18.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4926  -23.6008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8017  -23.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9238  -23.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2618  -18.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7457  -17.9696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2691  -17.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4904  -17.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4860  -18.3712    0.0000 O   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
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  5 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525316

   ---

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: 333.30

Molecular Weight (Monoisotopic): 333.1073

AlogP: -0.72

#Rotatable Bonds: 3

Polar Surface Area: 152.68

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 7.00

CX LogP: -1.31

CX LogD: -1.33

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.49

Np Likeness Score: 0.89

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