(S)-2,6-Diamino-N6-propyl-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine

ID: ALA1766197

PubChem CID: 54585362

Max Phase: Preclinical

Molecular Formula: C12H20FN6O4P

Molecular Weight: 362.30

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCNc1nc(N)nc2c1ncn2C[C@@H](CF)OCP(=O)(O)O

Standard InChI:  InChI=1S/C12H20FN6O4P/c1-2-3-15-10-9-11(18-12(14)17-10)19(6-16-9)5-8(4-13)23-7-24(20,21)22/h6,8H,2-5,7H2,1H3,(H2,20,21,22)(H3,14,15,17,18)/t8-/m1/s1

Standard InChI Key:  FMLCEUSRKWMBON-MRVPVSSYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    8.2611  -11.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2599  -12.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9747  -12.6569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9729  -11.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6883  -11.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6886  -12.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4791  -12.4999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9674  -11.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4786  -11.1560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451  -12.6560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9705  -10.1789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8870  -13.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7119  -13.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1198  -13.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1290  -12.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9540  -12.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3711  -11.8040    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.9448  -13.9447    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6837   -9.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1961  -11.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9632  -11.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9507  -12.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3994  -10.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1126   -9.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  2  2  0
 13 15  1  6
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4  1  1  0
 14 18  1  0
  2 10  1  0
 11 19  1  0
  5  6  1  0
  4 11  1  0
 17 20  1  0
  7 12  1  0
 17 21  2  0
  2  3  1  0
 17 22  1  0
 12 13  1  0
 19 23  1  0
  3  6  2  0
 23 24  1  0
M  END

Associated Targets(Human)

CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADA Tclin Adenosine deaminase (129 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Human immunodeficiency virus 1 (70413 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human immunodeficiency virus 2 (5592 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Moloney murine sarcoma virus (182 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 362.30Molecular Weight (Monoisotopic): 362.1268AlogP: 0.72#Rotatable Bonds: 9
Polar Surface Area: 148.41Molecular Species: ACIDHBA: 8HBD: 4
#RO5 Violations: HBA (Lipinski): 10HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: -5.43CX Basic pKa: 6.39CX LogP: -3.18CX LogD: -2.66
Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.47Np Likeness Score: -0.65

References

1. Baszczyňski O, Jansa P, Dračínský M, Klepetářová B, Holý A, Votruba I, de Clercq E, Balzarini J, Janeba Z..  (2011)  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.,  19  (7): [PMID:21429755] [10.1016/j.bmc.2011.02.050]

Source