4-Amino-1-(3,4-dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-ethynyl-1H-pyrimidin-2-one

ID: ALA3350550

PubChem CID: 53781503

Max Phase: Preclinical

Molecular Formula: C11H13N3O4

Molecular Weight: 251.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1cn([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)c(=O)nc1N

Standard InChI:  InChI=1S/C11H13N3O4/c1-3-6-4-14(11(17)13-9(6)12)10-8(16)7(15)5(2)18-10/h1,4-5,7-8,10,15-16H,2H3,(H2,12,13,17)/t5-,7-,8-,10-/m1/s1

Standard InChI Key:  DVPHMOLRAZDTOU-VPCXQMTMSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    6.1471   -4.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -4.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1032   -2.9409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3186   -3.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5448   -4.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602   -4.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950   -3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7163   -3.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -5.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276   -4.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1579   -4.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2825   -5.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7710   -5.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -2.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5010   -3.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950   -2.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -4.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -5.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  4  1  0
  4  1  1  0
  5  6  2  0
  6  1  1  0
  7  2  1  0
  8  5  1  0
  9  2  1  0
 10  7  1  0
 11  5  1  0
 12  9  1  0
 13 11  3  0
 14  4  2  0
 15  8  1  0
  7 16  1  1
 10 17  1  1
 12 18  1  6
  3  8  2  0
 12 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350550

   4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-ethynylpyrimidin-2-one

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: 251.24

Molecular Weight (Monoisotopic): 251.0906

AlogP: -1.55

#Rotatable Bonds: 1

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.59

CX Basic pKa: ┄

CX LogP: -1.72

CX LogD: -1.72

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.52

Np Likeness Score: 0.80

References

1. Hattori K, Kohchi Y, Oikawa N, Suda H, Ura M, Ishikawa T, Miwa M, Endoh M, Eda H, Tanimura H, Kawashima A, Horii I, Ishitsuka H, Shimma N..  (2003)  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine.,  13  (5): [PMID:12617910] [10.1016/s0960-894x(02)01082-x]

Source

Source(1):

• Scientific Literature