(3R,4S,5S,6R)-3-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol

ID: ALA2068864

PubChem CID: 2737302

Max Phase: Preclinical

Molecular Formula: C6H11FO5

Molecular Weight: 182.15

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): [18F]-Fluorodeoxyglucose

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

Standard InChI:  InChI=1S/C6H11FO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1H2/t2-,3-,4-,5-,6?/m1/s1

Standard InChI Key:  ZCXUVYAZINUVJD-IVMDWMLBSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
   13.5430  -12.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5430  -14.4791    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.1133  -15.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6877  -14.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1132  -12.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0608  -13.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8322  -13.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8322  -14.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1132  -14.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4025  -14.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4025  -13.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6877  -12.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
 11  5  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  0
  8  2  1  6
  9  3  1  1
 10  4  1  6
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2068864

   2-deoxy-2-((18)F)fluoro-D-glucopyranose

2. Parent:

   

   ALA2068864

   (3R,4S,5S,6R)-3-fluoro-6-(hydroxymethyl)oxane-2,4,5-triol

Molecule Features

Natural Product: Yes

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: 182.15

Molecular Weight (Monoisotopic): 182.0591

AlogP: -2.24

#Rotatable Bonds: 1

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: -2.04

CX LogD: -2.04

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.37

Np Likeness Score: 1.83

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]

2. Wijayasinghe YS, Bhansali MP, Borkar MR, Chaturbhuj GU, Muntean BS, Viola RE, Bhansali PR..  (2022)  A Comprehensive Biological and Synthetic Perspective on 2-Deoxy-d-Glucose (2-DG), A Sweet Molecule with Therapeutic and Diagnostic Potentials.,  65  (5.0): [PMID:35192360] [10.1021/acs.jmedchem.1c01737]

Source

Source(1):

• Scientific Literature