2-Amino-9-(4-hydroxy-butyl)-1,9-dihydro-purin-6-one

ID: ALA258513

PubChem CID: 135433410

Max Phase: Preclinical

Molecular Formula: C9H13N5O2

Molecular Weight: 223.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ncn2CCCCO)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H13N5O2/c10-9-12-7-6(8(16)13-9)11-5-14(7)3-1-2-4-15/h5,15H,1-4H2,(H3,10,12,13,16)

Standard InChI Key:  DVQJDXCYEPGOCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   -0.0420   -0.5058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -1.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903   -0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -0.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581   -0.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -1.5874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595   -1.7474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709    0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -2.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2431   -2.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035   -3.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3115   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5718   -4.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  1  2  1  0
  4  9  1  0
  9  8  1  0
  2  3  2  0
  2 10  1  0
  3  4  1  0
  6 11  2  0
  4  5  2  0
  9 12  1  0
  5  6  1  0
 12 13  1  0
 13 14  1  0
  5  7  1  0
 14 15  1  0
  1  6  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA258513

   ---

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: 223.24

Molecular Weight (Monoisotopic): 223.1069

AlogP: -0.53

#Rotatable Bonds: 4

Polar Surface Area: 109.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.17

CX Basic pKa: 0.55

CX LogP: -1.04

CX LogD: -1.04

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.60

Np Likeness Score: -0.40

References

1. Ashton WT, Meurer LC, Cantone CL, Field AK, Hannah J, Karkas JD, Liou R, Patel GF, Perry HC, Wagner AF..  (1988)  Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.,  31  (12): [PMID:2848125] [10.1021/jm00120a010]

2. Legraverend M, Boumchita H, Zerial A, Huel C, Lemaitre M, Bisagni E..  (1990)  Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.,  33  (9): [PMID:2391689] [10.1021/jm00171a022]

3. Niwas S, Chand P, Pathak VP, Montgomery JA..  (1994)  Structure-based design of inhibitors of purine nucleoside phosphorylase. 5. 9-Deazahypoxanthines.,  37  (15): [PMID:8057293] [10.1021/jm00041a027]

4. Xu H, Maga G, Focher F, Smith ER, Spadari S, Gambino J, Wright GE..  (1995)  Synthesis, properties, and pharmacokinetic studies of N2-phenylguanine derivatives as inhibitors of herpes simplex virus thymidine kinases.,  38  (1): [PMID:7837239] [10.1021/jm00001a010]

5. Manikowski A, Verri A, Lossani A, Gebhardt BM, Gambino J, Focher F, Spadari S, Wright GE..  (2005)  Inhibition of herpes simplex virus thymidine kinases by 2-phenylamino-6-oxopurines and related compounds: structure-activity relationships and antiherpetic activity in vivo.,  48  (11): [PMID:15916444] [10.1021/jm049059x]

6. Focher F, Lossani A, Verri A, Spadari S, Maioli A, Gambino JJ, Wright GE, Eberle R, Black DH, Medveczky P, Medveczky M, Shugar D..  (2007)  Sensitivity of monkey B virus (Cercopithecine herpesvirus 1) to antiviral drugs: role of thymidine kinase in antiviral activities of substrate analogs and acyclonucleosides.,  51  (6): [PMID:17438061] [10.1128/aac.01284-06]

7. Mohammed AF, Andrei G, Hayallah AM, Abdel-Moty SG, Snoeck R, Simons C..  (2019)  Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.,  27  (6): [PMID:30738653] [10.1016/j.bmc.2019.02.005]

Source

Source(1):

• Scientific Literature