2'-Deoxyzebularine 5'-[4-chlorophenyl(ethoxy-L-alaninyl)]phosphate

ID: ALA515534

PubChem CID: 25155322

Max Phase: Preclinical

Molecular Formula: C20H25ClN3O8P

Molecular Weight: 501.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](C)NP(=O)(OC[C@H]1O[C@@H](n2cccnc2=O)C[C@@H]1O)Oc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H25ClN3O8P/c1-3-29-19(26)13(2)23-33(28,32-15-7-5-14(21)6-8-15)30-12-17-16(25)11-18(31-17)24-10-4-9-22-20(24)27/h4-10,13,16-18,25H,3,11-12H2,1-2H3,(H,23,28)/t13-,16-,17+,18+,33?/m0/s1

Standard InChI Key:  ALSRZNMLVMFDBF-YEKMMIMBSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    0.6920   -9.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5170   -9.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7720   -8.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -8.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371   -8.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071  -10.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566   -8.4113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693   -8.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510   -8.7187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -7.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -7.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262   -7.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -9.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475   -8.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -7.3493    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037   -7.1315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -6.5588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -8.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -7.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823   -7.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0676   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8574   -8.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -9.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -8.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2652   -6.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0294   -5.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015   -6.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7721   -5.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973   -4.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -5.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4423   -9.4538    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -5.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  2  3  1  0
 16 17  1  0
  3  4  1  0
 16 18  1  0
  4  5  1  0
 16 19  2  0
  5  1  1  0
 17 20  1  0
  1  2  1  0
 20 21  2  0
  7 12  1  0
 21 22  1  0
  8  9  1  0
 22 23  2  0
  9 10  2  0
 23 24  1  0
 10 11  1  0
 24 25  2  0
 25 20  1  0
 11 12  2  0
 18 26  1  0
  1  6  1  6
 26 27  1  0
  8 13  2  0
 26 28  1  6
  5 14  1  1
 27 29  1  0
 27 30  2  0
  3  7  1  1
 29 31  1  0
 14 15  1  0
 23 32  1  0
  7  8  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515534

   ethyl (2S)-2-[[(4-chlorophenoxy)-[[(2R,3S,5R)-3-hydroxy-5-(2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]amino]propanoate

Molecule Features

Natural Product: No

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: 501.86

Molecular Weight (Monoisotopic): 501.1068

AlogP: 2.29

#Rotatable Bonds: 10

Polar Surface Area: 138.21

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 1.41

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -0.09

References

1. Yoo CB, Valente R, Congiatu C, Gavazza F, Angel A, Siddiqui MA, Jones PA, McGuigan C, Marquez VE..  (2008)  Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2'-deoxyzebularine.,  51  (23): [PMID:19006382] [10.1021/jm8005965]

Source

Source(1):

• Scientific Literature