5-cyano-2'-deoxyuridine 5'-monophosphate

ID: ALA3246102

PubChem CID: 54061885

Max Phase: Preclinical

Molecular Formula: C10H12N3O8P

Molecular Weight: 333.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H12N3O8P/c11-2-5-3-13(10(16)12-9(5)15)8-1-6(14)7(21-8)4-20-22(17,18)19/h3,6-8,14H,1,4H2,(H,12,15,16)(H2,17,18,19)/t6-,7+,8+/m0/s1

Standard InChI Key:  MAHMBNBBSHVKPJ-XLPZGREQSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    4.5845   -4.1440    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -4.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937   -4.8616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623   -7.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3397   -6.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -6.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -5.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4013   -5.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7627   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3223   -5.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022   -4.5348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1812   -5.3234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8937   -5.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6006   -5.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5830   -4.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8664   -4.0831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1675   -4.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -4.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4524   -4.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3160   -5.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -3.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0305   -6.0812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  6  1  0
  5  7  1  0
  6  8  1  0
  7  9  1  0
  8  9  1  0
  5  4  1  6
 10 11  1  0
  7 10  1  1
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
  8 12  1  1
 15 18  2  0
 17 19  2  0
 14 20  1  0
 11  1  1  0
  1 21  2  0
 20 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246102

   [(2R,3S,5R)-5-(5-cyano-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 333.19

Molecular Weight (Monoisotopic): 333.0362

AlogP: -1.83

#Rotatable Bonds: 4

Polar Surface Area: 174.87

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.83

CX LogD: -7.06

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.46

Np Likeness Score: 0.49

References

1. Chang CT, Edwards MW, Torrence PF, Mertes MP..  (1979)  5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.,  22  (9): [PMID:114660] [10.1021/jm00195a028]

Source

Source(1):

• Scientific Literature