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

ID: ALA3350549

PubChem CID: 54515638

Max Phase: Preclinical

Molecular Formula: C9H12IN3O4

Molecular Weight: 353.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](n2cc(I)c(N)nc2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C9H12IN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5-,6-,8-/m1/s1

Standard InChI Key:  YMFSDPSSPUNGFD-ZIYNGMLESA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    5.4493   -0.9658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647   -1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055    0.0961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208   -0.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973   -0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8470   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0186   -0.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098   -2.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298   -1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848   -2.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    0.3932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601   -1.8149    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.8032   -0.2010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973    0.0892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -0.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998   -2.6728    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  1  1  0
  6  2  1  0
  7  5  2  0
  8  7  1  0
  9  2  1  0
 10  6  1  0
 11  9  1  0
 12  4  2  0
 13  7  1  0
 14  8  1  0
  6 15  1  1
 10 16  1  1
 11 17  1  6
  3  8  2  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350549

   4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-iodopyrimidin-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: 353.12

Molecular Weight (Monoisotopic): 352.9873

AlogP: -0.93

#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: -0.76

CX LogD: -0.76

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 1.08

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