5-(6-Amino-purin-9-yl)-4,4-difluoro-2-hydroxymethyl-tetrahydro-furan-3-ol

ID: ALA2112593

PubChem CID: 6474638

Max Phase: Preclinical

Molecular Formula: C10H11F2N5O3

Molecular Weight: 287.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@H]1O[C@@H](CO)[C@H](O)C1(F)F

Standard InChI:  InChI=1S/C10H11F2N5O3/c11-10(12)6(19)4(1-18)20-9(10)17-3-16-5-7(13)14-2-15-8(5)17/h2-4,6,9,18-19H,1H2,(H2,13,14,15)/t4-,6-,9-/m0/s1

Standard InChI Key:  CHTZUQHTKOSZKY-AKSUTBOMSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    4.0720   -2.5114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315   -5.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720   -4.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -2.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5351   -1.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226   -1.3149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4733   -5.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226   -2.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0274   -4.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8964   -4.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -0.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -2.4614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1065   -1.3149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1065   -2.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -6.1467    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1093   -4.7681    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7099   -6.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026   -0.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9146   -3.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6790   -3.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  1
  4  1  1  0
  5  4  2  0
  6  8  2  0
  7  2  1  0
  8  1  1  0
  9  3  1  0
 10  9  1  0
 11  5  1  0
 12  4  1  0
 13 14  1  0
 14 12  2  0
 15  2  1  0
 16  2  1  0
  7 17  1  6
 18 11  1  0
 10 19  1  1
 20 19  1  0
  5  6  1  0
  7 10  1  0
 11 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112593

   (2S,3S,5S)-5-(6-aminopurin-9-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

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: 287.23

Molecular Weight (Monoisotopic): 287.0830

AlogP: -0.71

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.51

CX Basic pKa: 3.92

CX LogP: -0.76

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: 0.99

References

1. Kotra LP, Xiang Y, Newton MG, Schinazi RF, Cheng YC, Chu CK..  (1997)  Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides.,  40  (22): [PMID:9357530] [10.1021/jm970275y]

2. Yuejun Xiang, Kotra LP, Chu CK, Schinazi RF.  (1995)  Synthesis and anti-HIV activities of 2-deoxy-2,2-difluoro--L-ribofuranosyl-pyrimidine and -purine nucleosides,  5  (7): [10.1016/0960-894X(95)00107-5]

3. Lin X, Liang C, Zou L, Yin Y, Wang J, Chen D, Lan W..  (2021)  Advance of structural modification of nucleosides scaffold.,  214  [PMID:33550179] [10.1016/j.ejmech.2021.113233]

Source

Source(1):

• Scientific Literature