5-mercapto-2'-deoxyuridine-5'-phosphate

ID: ALA3228321

Cas Number: 28456-57-7

PubChem CID: 54235934

Max Phase: Preclinical

Molecular Formula: C9H13N2O8PS

Molecular Weight: 340.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1S

Standard InChI:  InChI=1S/C9H13N2O8PS/c12-4-1-7(19-5(4)3-18-20(15,16)17)11-2-6(21)8(13)10-9(11)14/h2,4-5,7,12,21H,1,3H2,(H,10,13,14)(H2,15,16,17)/t4-,5+,7+/m0/s1

Standard InChI Key:  QMONXJFWUJBENE-HBPOCXIASA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   10.1609   -7.1314    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.6345   -6.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2969   -5.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7705   -5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5877   -5.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0743   -5.7019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8306   -4.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1667   -3.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5124   -4.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1587   -2.9771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8637   -2.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5727   -2.9632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8557   -1.7444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1426   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1346   -0.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4376   -1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4456   -2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7286   -1.3567    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3473   -7.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5019   -7.8740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752   -7.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4  9  1  0
  8 10  1  1
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 10 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  2  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3228321

   2'-Deoxy-5-sulfanyluridine 5'-(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: 340.25

Molecular Weight (Monoisotopic): 340.0130

AlogP: -1.42

#Rotatable Bonds: 4

Polar Surface Area: 151.08

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.37

CX LogD: -5.52

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.33

Np Likeness Score: 0.80

References

1. Choi S, Kalman TI, Bardos TJ..  (1979)  Synthesis of 5-selenium-substituted uracil derivatives. Inhibition of thymidylate synthetase by 5-hydroseleno-2'-deoxyuridylate.,  22  (6): [PMID:110931] [10.1021/jm00192a004]

2. 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