(3R,4S,5R,6R)-6-(acetoxymethyl)-3-fluorotetrahydro-2H-pyran-2,4,5-triyl triacetate

ID: ALA4214876

Cas Number: 31077-89-1

PubChem CID: 11688873

Max Phase: Preclinical

Molecular Formula: C14H19FO9

Molecular Weight: 350.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1OC(OC(C)=O)[C@H](F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C14H19FO9/c1-6(16)20-5-10-12(21-7(2)17)13(22-8(3)18)11(15)14(24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12-,13-,14?/m1/s1

Standard InChI Key:  KIPRSJXOVDEYLX-GNMOMJPPSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    6.8718   -8.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8718   -9.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771  -10.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2824   -9.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2824   -8.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771   -8.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1629   -8.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1605   -7.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1647  -10.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771  -10.9206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9895  -10.1086    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9913   -8.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -7.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492   -6.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451   -7.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4564   -9.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493  -10.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4552   -8.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8694  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8694  -12.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1617  -10.9206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6978   -8.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4067   -8.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6954   -9.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  1
  7  8  1  0
  2  9  1  6
  3 10  1  1
  4 11  1  6
  5 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  2  0
 12 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214876

   [(2R,3R,4S,5R)-3,4,6-triacetyloxy-5-fluorooxan-2-yl]methyl acetate

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: 350.30

Molecular Weight (Monoisotopic): 350.1013

AlogP: 0.04

#Rotatable Bonds: 5

Polar Surface Area: 114.43

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.28

CX LogD: -0.28

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 1.38

References

1. El Hilali M, Reux B, Debiton E, Leal F, Galmier MJ, Vivier M, Chezal JM, Miot-Noirault E, Coudert P, Weber V..  (2017)  Linker structure-activity relationships in fluorodeoxyglucose chlorambucil conjugates for tumor-targeted chemotherapy.,  25  (20): [PMID:28927903] [10.1016/j.bmc.2017.08.043]

Source

Source(1):

• Scientific Literature