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

ID: ALA5200809

PubChem CID: 168290377

Max Phase: Preclinical

Molecular Formula: C15H31N4O6P

Molecular Weight: 293.22

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H16N3O6P.C6H15N/c1-9(5-13,18-6-19(15,16)17)4-12-3-2-7(10)11-8(12)14;1-4-7(5-2)6-3/h2-3,13H,4-6H2,1H3,(H2,10,11,14)(H2,15,16,17);4-6H2,1-3H3

Standard InChI Key:  OAYMVQVCNGLJOW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
   -0.1711   -2.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469   -2.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650   -2.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893   -2.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075   -2.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -1.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893   -1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    1.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911    1.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    1.9853    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    1.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233    1.5720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5051    2.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    1.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    1.5720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911    0.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051    0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233    0.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051    1.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911    1.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    0.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    2.3986    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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 18 24  1  0
 19 25  2  0
 10 26  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: 293.22

Molecular Weight (Monoisotopic): 293.0777

AlogP: -1.27

#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: -2.12

CX LogD: -4.55

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.47

Np Likeness Score: 0.06

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