(R,S)-(2-Ethyny1-3-hydroxy-2-(phosphonomethoxy)propy)-thymine Triethylammonium Salt

ID: ALA5176197

PubChem CID: 168273075

Max Phase: Preclinical

Molecular Formula: C17H30N3O7P

Molecular Weight: 318.22

Names and Identifiers

Canonical SMILES:  C#CC(CO)(Cn1cc(C)c(=O)[nH]c1=O)OCP(=O)(O)O.CCN(CC)CC

Standard InChI:  InChI=1S/C11H15N2O7P.C6H15N/c1-3-11(6-14,20-7-21(17,18)19)5-13-4-8(2)9(15)12-10(13)16;1-4-7(5-2)6-3/h1,4,14H,5-7H2,2H3,(H,12,15,16)(H2,17,18,19);4-6H2,1-3H3

Standard InChI Key:  YFKWDINOSGARRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.3544    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    1.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765    1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    1.4966    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1985    1.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3544    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675    1.0861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -0.1450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3544    1.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3502    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -2.3133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319   -2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2450   -2.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073   -2.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -1.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -1.0778    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: 318.22

Molecular Weight (Monoisotopic): 318.0617

AlogP: -1.64

#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: -1.81

CX LogD: -4.23

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.36

Np Likeness Score: -0.25

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