((2R,3S,4R,5R)-3,4-dihydroxy-5-(5-(hydroxymethyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate

ID: ALA3274191

PubChem CID: 54443874

Max Phase: Preclinical

Molecular Formula: C10H15N2O10P

Molecular Weight: 354.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)cc1CO

Standard InChI:  InChI=1S/C10H15N2O10P/c13-2-4-1-12(10(17)11-8(4)16)9-7(15)6(14)5(22-9)3-21-23(18,19)20/h1,5-7,9,13-15H,2-3H2,(H,11,16,17)(H2,18,19,20)/t5-,6-,7-,9-/m1/s1

Standard InChI Key:  WQCABYUOJVUOEC-JXOAFFINSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   13.9615   -6.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4476   -5.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2722   -5.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2039   -5.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5154   -5.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8705   -4.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4204   -4.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4001   -4.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3062   -4.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9198   -5.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7063   -5.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751   -4.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2529   -3.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4706   -4.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7588   -6.6659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7552   -6.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6575   -4.1603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6755   -3.7465    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.6550   -2.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8471   -3.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4555   -4.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4176   -3.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2001   -2.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  2  1  1  6
  7  8  1  0
  4  7  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  5  9  1  1
  3 15  1  6
 10 16  2  0
 12 17  2  0
  8 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  2  0
 13 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3274191

   [(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-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: 354.21

Molecular Weight (Monoisotopic): 354.0464

AlogP: -3.24

#Rotatable Bonds: 5

Polar Surface Area: 191.54

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -3.42

CX LogD: -6.96

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 1.21

References

1. 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