ID: ALA195923

Max Phase: Phase

Molecular Formula: C6H12O6

Molecular Weight: 180.16

Molecule Type: Small molecule

Representations

Synonyms (3): D-galactose | Galactose | NSC-8102
Synonyms from Alternative Forms(3):

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

Standard InChI:  InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6?/m1/s1

Standard InChI Key:  WQZGKKKJIJFFOK-SVZMEOIVSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 180.16

Molecular Weight (Monoisotopic): 180.0634

AlogP: -3.22

#Rotatable Bonds: 1

Polar Surface Area: 110.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.30

CX Basic pKa:

CX LogP: -2.93

CX LogD: -2.93

Aromatic Rings: 0

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 2.63

References

1. Sufrin JR, Bernacki RJ, Morin MJ, Korytnyk W..  (1980)  Halogenated L-fucose and D-galactose analogues: synthesis and metabolic effects.,  23  (2): [PMID:7359528] [10.1021/jm00176a008]

2. Dumas DP, Ichikawa Y, Wong C, Lowe JB, Nair RP.  (1991)  Enzymatic synthesis of sialyl Lex and derivatives based on a recombinant fucosyltransferase,  1  (8): [10.1016/S0960-894X(00)80270-X]

3. Tejler J, Leffler H, Nilsson UJ..  (2005)  Synthesis of O-galactosyl aldoximes as potent LacNAc-mimetic galectin-3 inhibitors.,  15  (9): [PMID:15837322] [10.1016/j.bmcl.2005.02.079]

4. Bhat N, Joe A, PereiraPerrin M, Ward HD..  (2007)  Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.,  282  (48): [PMID:17905738] [10.1074/jbc.m706950200]

5. Lairson LL, Watts AG, Wakarchuk WW, Withers SG..  (2006)  Using substrate engineering to harness enzymatic promiscuity and expand biological catalysis.,  2  (12): [PMID:17057723] [10.1038/nchembio828]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. Boyd RE, Lee G, Rybczynski P, Benjamin ER, Khanna R, Wustman BA, Valenzano KJ..  (2013)  Pharmacological chaperones as therapeutics for lysosomal storage diseases.,  56  (7): [PMID:23363020] [10.1021/jm301557k]

9. PubChem BioAssay data set, 

10. Pera NP, Pieters RJ.  (2014)  Towards bacterial adhesion-based therapeutics and detection methods,  5  (8): [10.1039/C3MD00346A]

11. Nkosana NK, Czyzyk DJ, Siegel ZS, Cote JM, Taylor EA..  (2018)  Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.,  28  (4): [PMID:29398539] [10.1016/j.bmcl.2018.01.040]

12. Unpublished dataset, 

13. D'Ambrosio EA, Drake WR, Mashayekh S, Ukaegbu OI, Brown AR, Grimes CL..  (2019)  Modulation of the NOD-like receptors NOD1 and NOD2: A chemist's perspective.,  29  (10): [PMID:30890292] [10.1016/j.bmcl.2019.03.010]

14.  (2014)  Fibcd1 for the prevention and treatment of diseases, 

15. Zomer-van Ommen DD, Pukin AV, Fu O, Quarles van Ufford LH, Janssens HM, Beekman JM, Pieters RJ..  (2016)  Functional Characterization of Cholera Toxin Inhibitors Using Human Intestinal Organoids.,  59  (14): [PMID:27347611] [10.1021/acs.jmedchem.6b00770]

16. Singh K, Kulkarni SS..  (2022)  Small Carbohydrate Derivatives as Potent Antibiofilm Agents.,  65  (13.0): [PMID:35777073] [10.1021/acs.jmedchem.1c01039]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Patent Bioactivity Data