2-Amino-8-bromo-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

ID: ALA3143046

Cas Number: 13389-03-2

PubChem CID: 135437126

Product Number: B122946, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H12BrN5O4

Molecular Weight: 346.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2nc(Br)n([C@H]3C[C@H](O)[C@@H](CO)O3)c2n1

Standard InChI:  InChI=1S/C10H12BrN5O4/c11-9-13-6-7(14-10(12)15-8(6)19)16(9)5-1-3(18)4(2-17)20-5/h3-5,17-18H,1-2H2,(H3,12,14,15,19)/t3-,4+,5+/m0/s1

Standard InChI Key:  MKDXZFVCXWXGBQ-VPENINKCSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.9046   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200   -0.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -2.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351   -1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200   -2.2633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -0.7708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -0.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336   -2.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    0.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -3.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -1.5958    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0480   -0.7708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130    1.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    1.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680    2.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  2  0
  7  2  1  1
  8  3  2  0
  9 10  2  0
 10  6  1  0
 11  7  1  0
 12  7  1  0
 13 11  1  0
 14 12  1  0
 15  8  1  0
 16  4  1  0
 17 10  1  0
 14 18  1  6
 13 19  1  1
 20 19  1  0
  5  4  2  0
  9  8  1  0
 14 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3143046

   8-Bromo-2'-deoxyguanosine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.14

Molecular Weight (Monoisotopic): 345.0073

AlogP: -0.48

#Rotatable Bonds: 2

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.43

CX Basic pKa: ┄

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: 0.66

References

1. Lin TS, Cheng JC, Ishiguro K, Sartorelli AC..  (1985)  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.,  28  (9): [PMID:3861870] [10.1021/jm00147a012]

Source

Source(1):

• Scientific Literature