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

ID: ALA5172019

PubChem CID: 168270789

Max Phase: Preclinical

Molecular Formula: C17H29N6O5P

Molecular Weight: 327.24

Names and Identifiers

Canonical SMILES:  C#CC(CO)(Cn1cnc2c(N)ncnc21)OCP(=O)(O)O.CCN(CC)CC

Standard InChI:  InChI=1S/C11H14N5O5P.C6H15N/c1-2-11(4-17,21-7-22(18,19)20)3-16-6-15-8-9(12)13-5-14-10(8)16;1-4-7(5-2)6-3/h1,5-6,17H,3-4,7H2,(H2,12,13,14)(H2,18,19,20);4-6H2,1-3H3

Standard InChI Key:  QVDFWQYJBZNYIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.6892   -2.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4033   -2.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -2.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -2.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246   -1.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325    1.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566    1.6090    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566    0.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    1.1953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566    2.4322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0956    1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    1.1953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7111    0.2075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5507    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8223    2.3210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.8806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    1.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687    0.4833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    2.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6103    2.8435    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
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  9 10  1  0
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 21 26  1  0
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 10 28  1  0
 28 29  3  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: 327.24

Molecular Weight (Monoisotopic): 327.0733

AlogP: -1.08

#Rotatable Bonds: 6

Polar Surface Area: 156.61

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 4.68

CX LogP: -4.40

CX LogD: -4.54

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -0.21

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