[5-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (CidUMP)

ID: ALA1236538

Cas Number: 64334-79-8

PubChem CID: 16721025

Max Phase: Preclinical

Molecular Formula: C9H12ClN2O8P

Molecular Weight: 342.63

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)cc1Cl

Standard InChI:  InChI=1S/C9H12ClN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1

Standard InChI Key:  RBQXEHDSKLSKLJ-RRKCRQDMSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.0876    3.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    2.9448    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126    2.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2626    2.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    2.1198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731    1.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731    0.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943    0.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    0.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252    0.6523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856   -0.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -0.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243   -1.0547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317   -1.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6737   -2.4758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -2.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791   -3.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297   -1.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3448   -0.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -1.5496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  4  2  1  0
  5  2  1  0
  6  5  1  0
  7  6  1  1
  7  8  1  0
  9  7  1  0
 12  8  1  0
  9 10  1  6
 11  9  1  0
 12 11  1  0
 12 13  1  1
 14 13  1  0
 20 13  1  0
 14 15  2  0
 14 16  1  0
 17 16  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1236538

   5-Chloro-2'-deoxyuridine 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: 342.63

Molecular Weight (Monoisotopic): 342.0020

AlogP: -1.05

#Rotatable Bonds: 4

Polar Surface Area: 151.08

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -0.98

CX LogD: -4.54

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 0.85

References

1. Coderre JA, Santi DV, Matsuda A, Watanabe KA, Fox JJ..  (1983)  Mechanism of action of 2',5-difluoro-1-arabinosyluracil.,  26  (8): [PMID:6876083] [10.1021/jm00362a012]

2. Barr PJ, Nolan PA, Santi DV, Robins MJ..  (1981)  Inhibition of thymidylate synthetase by 5-alkynyl-2'-deoxyuridylates.,  24  (12): [PMID:6796687] [10.1021/jm00144a003]

3. Felczak K, Miazga A, Poznański J, Bretner M, Kulikowski T, Dzik JM, Gołos B, Zieliński Z, Cieśla J, Rode W..  (2000)  5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.,  43  (24): [PMID:11101356] [10.1021/jm000975u]

4. 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]

5. Wataya Y, Santi DV, Hansch C..  (1977)  Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.,  20  (11): [PMID:410930] [10.1021/jm00221a021]

Source

Source(1):

• Scientific Literature