(2S,4R)-(-)-9-{2-[4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]methoxyethyl}adenine

ID: ALA3350247

PubChem CID: 11396132

Max Phase: Preclinical

Molecular Formula: C17H19ClN5O4P

Molecular Weight: 423.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2CCOC[P@]1(=O)OCC[C@H](c2cccc(Cl)c2)O1

Standard InChI:  InChI=1S/C17H19ClN5O4P/c18-13-3-1-2-12(8-13)14-4-6-26-28(24,27-14)11-25-7-5-23-10-22-15-16(19)20-9-21-17(15)23/h1-3,8-10,14H,4-7,11H2,(H2,19,20,21)/t14-,28+/m1/s1

Standard InChI Key:  GWNHAOBXDGOXRR-SUMNFNSASA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    6.6473  -26.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6473  -26.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3600  -27.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0727  -26.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0727  -26.0832    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.3600  -25.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0572  -23.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7200  -23.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7172  -22.7557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0554  -22.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4001  -23.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4013  -22.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6751  -22.5043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2322  -23.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731  -23.8385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0535  -21.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3171  -24.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5533  -24.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1927  -25.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4371  -25.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7491  -26.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9309  -25.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9274  -24.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118  -24.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034  -24.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066  -25.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2181  -26.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7931  -26.0975    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  1  2  1  0
 10 16  1  0
  7  8  2  0
 15 17  1  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  2  3  1  0
 19 20  1  0
  5 20  1  6
  9 10  2  0
  5 21  2  0
 10 12  1  0
  1 22  1  6
 11 12  2  0
 22 23  2  0
  3  4  1  0
 23 24  1  0
  4  5  1  0
 24 25  2  0
  5  6  1  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 11  7  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350247

   9-[2-[[(2S,4R)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 423.80

Molecular Weight (Monoisotopic): 423.0863

AlogP: 3.41

#Rotatable Bonds: 6

Polar Surface Area: 114.38

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.75

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -0.70

References

1. Reddy KR, Matelich MC, Ugarkar BG, Gómez-Galeno JE, DaRe J, Ollis K, Sun Z, Craigo W, Colby TJ, Fujitaki JM, Boyer SH, van Poelje PD, Erion MD..  (2008)  Pradefovir: a prodrug that targets adefovir to the liver for the treatment of hepatitis B.,  51  (3): [PMID:18173234] [10.1021/jm7012216]

Source

Source(1):

• Scientific Literature