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

ID: ALA5169892

PubChem CID: 168269372

Max Phase: Preclinical

Molecular Formula: C16H29N4O6P

Molecular Weight: 303.21

Names and Identifiers

Canonical SMILES:  C#CC(CO)(Cn1ccc(N)nc1=O)OCP(=O)(O)O.CCN(CC)CC

Standard InChI:  InChI=1S/C10H14N3O6P.C6H15N/c1-2-10(6-14,19-7-20(16,17)18)5-13-4-3-8(11)12-9(13)15;1-4-7(5-2)6-3/h1,3-4,14H,5-7H2,(H2,11,12,15)(H2,16,17,18);4-6H2,1-3H3

Standard InChI Key:  WWHVWUTVPAFZET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.5469   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2649   -2.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074   -2.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -1.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -1.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911    1.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    1.7786    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    0.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232    1.3653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    2.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    1.3653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911    0.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051    0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    0.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051    1.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911    1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    0.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549    3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  5  1  0
  1  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  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: 303.21

Molecular Weight (Monoisotopic): 303.0620

AlogP: -1.66

#Rotatable Bonds: 6

Polar Surface Area: 147.90

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: ┄

CX LogP: -2.23

CX LogD: -4.65

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.36

Np Likeness Score: -0.02

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