2-Amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-dimethylamino-1,9-dihydro-purin-6-one

ID: ALA3246761

PubChem CID: 136227166

Max Phase: Preclinical

Molecular Formula: C12H18N6O5

Molecular Weight: 326.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nc2c(=O)[nH]c(N)nc2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H18N6O5/c1-17(2)12-14-5-8(15-11(13)16-9(5)22)18(12)10-7(21)6(20)4(3-19)23-10/h4,6-7,10,19-21H,3H2,1-2H3,(H3,13,15,16,22)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  UNMXHCVYRMWOEU-KQYNXXCUSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   10.7171  -19.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0974  -18.9334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4453  -18.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8001  -20.1924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3430  -19.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3810  -18.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2332  -18.1139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1849  -19.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5760  -20.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715  -18.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0865  -19.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2860  -20.0289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8399  -18.6852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6557  -21.3448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0264  -19.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2779  -19.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6306  -20.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2629  -18.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8299  -20.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2432  -18.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8777  -17.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2385  -16.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0138  -17.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  2  1  1
  2  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  2  0
  5 10  1  0
 11  5  1  0
  8 12  1  0
  8 13  2  0
  9 14  1  0
 10 15  1  0
 11 16  1  0
 11 17  1  6
 15 18  1  1
 16 19  1  6
 18 20  1  0
  6  7  2  0
  9 12  1  0
 16 15  1  0
  6 21  1  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246761

   ---

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: 326.31

Molecular Weight (Monoisotopic): 326.1339

AlogP: -2.62

#Rotatable Bonds: 3

Polar Surface Area: 162.75

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.16

CX Basic pKa: 0.71

CX LogP: -1.91

CX LogD: -1.91

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.68

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]

2. Jordan F, Wu A..  (1978)  Stereoelectronic factors in the binding of substrate analogues and inhibitors to purine nucleoside phosphorylase isolated from human erythrocytes.,  21  (9): [PMID:31484] [10.1021/jm00207a008]

Source

Source(1):

• Scientific Literature