(R,S)-(3-Hydroxy-2-methyl-2-(phosphonomethoxy)propy)-thymine Triethylammonium Salt

ID: ALA5171270

PubChem CID: 168269159

Max Phase: Preclinical

Molecular Formula: C16H32N3O7P

Molecular Weight: 308.23

Names and Identifiers

Canonical SMILES:  CCN(CC)CC.Cc1cn(CC(C)(CO)OCP(=O)(O)O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H17N2O7P.C6H15N/c1-7-3-12(9(15)11-8(7)14)4-10(2,5-13)19-6-20(16,17)18;1-4-7(5-2)6-3/h3,13H,4-6H2,1-2H3,(H,11,14,15)(H2,16,17,18);4-6H2,1-3H3

Standard InChI Key:  HPHQJODQACJAIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.0678    0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545    0.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545    1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    1.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769    1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    1.7022    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    0.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1991    1.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    2.5233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678    1.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678    0.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    0.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901    0.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901    1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545    2.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8189   -2.1086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455   -2.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6075   -2.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8189   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  2  0
  3 10  1  0
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 11 17  1  0
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  3 20  1  0
 21 22  1  0
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 21 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  0
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: 308.23

Molecular Weight (Monoisotopic): 308.0773

AlogP: -1.25

#Rotatable Bonds: 6

Polar Surface Area: 141.85

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: ┄

CX LogP: -1.70

CX LogD: -4.12

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: -0.19

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