4-amino-6-bromo-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

ID: ALA4553185

PubChem CID: 470024

Max Phase: Preclinical

Molecular Formula: C12H12BrN5O4

Molecular Weight: 370.16

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(Br)n([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12

Standard InChI:  InChI=1S/C12H12BrN5O4/c13-9-4(1-14)6-10(15)16-3-17-11(6)18(9)12-8(21)7(20)5(2-19)22-12/h3,5,7-8,12,19-21H,2H2,(H2,15,16,17)/t5-,7-,8-,12-/m1/s1

Standard InChI Key:  VGLVPHRWFSFJJL-JTFADIMSSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.1262   -4.2184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601   -4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976   -3.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9075   -3.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -2.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3389   -5.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -3.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0863   -5.2456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585   -6.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830   -6.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121   -2.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5955   -4.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100   -3.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3067   -3.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -5.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6154   -1.9418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -7.1002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -6.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -7.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -3.5597    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -1.3443    0.0000 N   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
  7 20  1  0
 21 22  3  0
  5 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553185

   (S)-4-Amino-6-bromo-7-((3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7,7a-dihydro-4aH-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

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: 370.16

Molecular Weight (Monoisotopic): 369.0073

AlogP: -0.74

#Rotatable Bonds: 2

Polar Surface Area: 150.44

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.67

CX LogP: -0.95

CX LogD: -0.95

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: 0.44

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