2'-Deoxyzebularine 3',5'-Bis[4-chlorophenyl(ethoxy-L-alaninyl)]phosphate

ID: ALA478399

PubChem CID: 25155848

Max Phase: Preclinical

Molecular Formula: C31H38Cl2N4O12P2

Molecular Weight: 791.52

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]1OP(=O)(N[C@@H](C)C(=O)OCC)Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C31H38Cl2N4O12P2/c1-5-43-29(38)20(3)35-50(41,47-24-12-8-22(32)9-13-24)45-19-27-26(18-28(46-27)37-17-7-16-34-31(37)40)49-51(42,36-21(4)30(39)44-6-2)48-25-14-10-23(33)11-15-25/h7-17,20-21,26-28H,5-6,18-19H2,1-4H3,(H,35,41)(H,36,42)/t20-,21-,26-,27+,28+,50?,51?/m0/s1

Standard InChI Key:  QOIYQCFJSVGDRR-HDHIHZQVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA478399

   ethyl (2S)-2-[[(4-chlorophenoxy)-[[(2R,3S,5R)-3-[(4-chlorophenoxy)-[[(2S)-1-ethoxy-1-oxopropan-2-yl]amino]phosphoryl]oxy-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: 791.52

Molecular Weight (Monoisotopic): 790.1339

AlogP: 5.70

#Rotatable Bonds: 18

Polar Surface Area: 191.84

Molecular Species: NEUTRAL

HBA: 14

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.94

CX Basic pKa: ┄

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 51

QED Weighted: 0.12

Np Likeness Score: -0.11

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