(R,S)-(2-Ethynyl-3-hydroxy-2-(phosphonomethoxy)propy)-guanine Triethylammonium Salt

ID: ALA5176564

PubChem CID: 168277787

Max Phase: Preclinical

Molecular Formula: C17H29N6O6P

Molecular Weight: 343.24

Names and Identifiers

Canonical SMILES:  C#CC(CO)(Cn1cnc2c(=O)[nH]c(N)nc21)OCP(=O)(O)O.CCN(CC)CC

Standard InChI:  InChI=1S/C11H14N5O6P.C6H15N/c1-2-11(4-17,22-6-23(19,20)21)3-16-5-13-7-8(16)14-10(12)15-9(7)18;1-4-7(5-2)6-3/h1,5,17H,3-4,6H2,(H2,19,20,21)(H3,12,14,15,18);4-6H2,1-3H3

Standard InChI Key:  BEKCKYLITXAUCX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.4196   -3.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377   -2.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014   -1.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196   -1.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360   -0.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0541    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681    1.3318    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681    0.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681    2.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5657    1.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    2.0416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6304    2.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8851    3.0019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857    1.5991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9268    0.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6179    2.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.24

Molecular Weight (Monoisotopic): 343.0682

AlogP: -1.78

#Rotatable Bonds: 6

Polar Surface Area: 176.58

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.35

CX Basic pKa: 0.34

CX LogP: -3.17

CX LogD: -5.36

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.30

Np Likeness Score: -0.09

References

1. Tan S, Groaz E, Kalkeri R, Ptak R, Korba BE, Herdewijn P..  (2022)  Reshaping an Acyclic Nucleoside Phosphonate into a Selective Anti-hepatitis B Virus Compound.,  65  (13.0): [PMID:35754374] [10.1021/acs.jmedchem.2c00667]

Source

Source(1):

• Scientific Literature