5'-Deoxy-5'-iodo-5-fluorouridine

ID: ALA3250417

Cas Number: 61787-13-1

PubChem CID: 10872387

Max Phase: Preclinical

Molecular Formula: C9H10FIN2O5

Molecular Weight: 372.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](CI)[C@@H](O)[C@H]2O)cc1F

Standard InChI:  InChI=1S/C9H10FIN2O5/c10-3-2-13(9(17)12-7(3)16)8-6(15)5(14)4(1-11)18-8/h2,4-6,8,14-15H,1H2,(H,12,16,17)/t4-,5-,6-,8-/m1/s1

Standard InChI Key:  KTXQKYNSEWRSDM-UAKXSSHOSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    4.1588   -9.5545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1577  -10.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8657  -10.7830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5754  -10.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5726   -9.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8639   -9.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2787   -9.1396    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8655  -11.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030  -12.0793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553  -12.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726  -12.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251  -12.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3024  -11.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7528  -13.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9748  -13.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621  -13.4320    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.4497  -10.7821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -8.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  1  0
  5  7  1  0
  8  3  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 12 13  1  6
 11 14  1  6
 10 15  1  1
 15 16  1  0
  2 17  2  0
  6 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250417

   5'-Deoxy-5'-iodo-5-fluorouridine

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: 372.09

Molecular Weight (Monoisotopic): 371.9618

AlogP: -1.27

#Rotatable Bonds: 2

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.12

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.44

Np Likeness Score: 0.58

References

1. Cook AF..  (1977)  Fluorinated Pyrimidine nucleosides. 1. Synthesis of a nitrogen analogue of the antitumor agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine hydrochloride.,  20  (3): [PMID:66315] [10.1021/jm00213a006]

Source

Source(1):

• Scientific Literature