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Leadscope Id LS-71022
CAS 7535-00-4
ChemSpider 22576
Pathway DBs
Assay DBs
PubChem CID 24154
Omics DBs
pKa 7.71
ToxCast Accepted no
Toxic Effect Apoptosis
ToxBank Accepted no

Executive Summary

Summary Information

The table listed below contains a summarized listing of toxic effect information leveraged from the 6th European Framework Programme project LIINTOP. For a complete listing of the Gold Compound evaluation criteria please see the Gold Compound Evaluation and Comments immediately following the summary table below.

SMILES C([C@@H]1[C@@H]([C@@H]([C@H](C(O1)O)N)O)O)O




Supplier Sigma Aldrich
Summary Hepatotoxic Effects from the LIINTOP FP6 Program
Hepatocellular necrosis.gif Apoptosis.gif Transporter inhibition.gif Cholestatic.gif Steatotic.gif Phospholipidosis.gif Hepatocyte function.gif Mithochondria impairment.gif Oxidative stress.gif DNA synthesis genotoxicity.gif Covalent binding.gif Idiosyncrasia metabolic.gif Idiosyncrasia immune.gif Bioactivation required.gif LIINTOP severity.gif References

[1] [2] [3] [4] [5] [6]

Gold Compound Evaluation and Comments

The following table is organized into four main sections and provides a detailed assessment by the Gold Compound Working Group for the use of this compound as a standard hepatotoxin. The table's four sections (collapsed by default but will expand when the "show" link is clicked) contains detailed information for the core set of SEURAT compound acceptance criteria.

Standard to Meet Compound Assessment
Criteria Notes
The in vivo therapeutic window is used to estimate an appropriate concentration for in vitro toxicity assays. This in vitro concentration should also be consistent with the exposure implied by pharmacokinetics parameters.
We prefer compounds that require metabolic activation, although standards that are active in themselves will be accepted if they have otherwise valuable properties. We require knowing the active metabolite, and we prefer compounds where the metabolite is stable and can be independently tested in order to verify the mechanism of toxicity as well as of metabolic activation in the test cell line.
Literature data for at least one, but not necessarily all, of the ‘omics datasets is desired. This requirement can be waived in special cases.
The IC50’s for in vitro efficacy and toxicity should be consistent with the therapeutic ratio observed in the clinic. These parameters will be dependent on specific cell type and culture conditions, but differences of more than 30-fold in the in vitro vs. in vivo therapeutic ratios should be considered suspect and carefully justified.
This is not a requirement, but compounds utilized in the EPA testing program can be assumed to have physical properties verified to be suitable for in vitro cellular assays.
Sparing soluble compounds may be assayed for solubility in serum and the percent serum used specified here.
This property will be measured when a sample of compound becomes available.

Proprietary Toxicity Literature Report

The toxicity literature report contains proprietary information and references for studies performed on this compound relevant to liver toxicity findings and is restricted for use within the SEURAT program only.

Toxicity Report

PubMed references

The following resource link will perform a PubMed query for the terms "Galactosamine" and "liver toxicity".
Galactosamine Search


  1. Gomez-Lechon, M.J., O’Connor, E., Castell, J.V., Jover, R., 2002. Sensitive markers used to identify compounds that trigger apoptosis in cultured hepatocytes. Toxicol. Sci. 65, 299–308.
  2. Feldmann, G., 2006. Liver apoptosis. Gastroenterol. Clin. Biol. 30, 533–545.
  3. Gomez-Lechon, M.J., O’Connor, E., Castell, J.V., Jover, R., 2002. Sensitive markers used to identify compounds that trigger apoptosis in cultured hepatocytes. Toxicol. Sci. 65, 299–308.
  4. Gomez-Lechon, M.J., O’Connor, J.E., Lahoz, A., Castell, J.V., Donato, M.T., 2008. Identification of apoptotic drugs: multiparametric evaluation in cultured hepatocytes. Curr. Med. Chem. 15, 2071–2085.
  5. Gomez-Lechon, M.J., Ponsoda, X., O’Connor, E., Donato, T., Jover, R., Castell, J.V., 2003. Diclofenac induces apoptosis in hepatocytes. Toxicol. in Vitro 17, 675– 680.
  6. Kass, G.E., Macanas-Pirard, P., Lee, P.C., Hinton, R.H., 2003. The role of apoptosis in acetaminophen-induced injury. Ann. NY Acad. Sci. 1010, 557–559.

Calculated/Predicted Properties

Water Solubility Results
pH Sol,mg/ml 7+ 0 7+,11- Graph
2 1000 100 - - Galactosamine solubility.png
5.5 1000 99.9 0.1 -
6.5 1000 99 1 -
7.4 1000 92.3 7.7 -
10 1000 2.9 96.4 0.1
Summary Solubility Data
Intrinsic Solubility,mg/ml 1000
Intrinsic Solubility,log(S,mol/l) 0.7467
Solubility in Pure Water at pH = 10.35,mg/ml 1000
Calculations performed using ACD/PhysChem v 9.14
LogD Results
pH LogD Graph
2 -5.19 Galactosamine logd.png
5.5 -4.83
6.5 -4.05
7.4 -3.2
10 -2.11
Calculations performed using ACD/PhysChem v 9.14
Single-valued Properties
Property Value Units Error
LogP -2.09 0.5
MW 179.17 -
PSA 116.17 -
FRB 6 -
HDonors 6 -
HAcceptors 6 -
Rule Of 5 1 -
Molar Refractivity 39.22 cm3 0.3
Molar Volume 114.6 cm3 3
Parachor 335.91 cm3 4
Index of Refraction 1.6 0.02
Surface Tension 73.81 dyne/cm 3
Density 1.56 g/cm3 0.06
Polarizability 15.55 10E-24 cm3 0.5
Calculations performed using ACD/PhysChem v 9.14
Property Name Value Units Source
pKa 7.71 SPARC v4.5
Estimated VP 2.02E-08 mm Hg EPI Suite v4.10
Estimated VP 2.69E-06 Pa EPI Suite v4.10
Estimated Water Solubility 1.00E+06 mg/L EPI Suite v4.10
WATERNT Frag Water Solubility Estimate 1.00E+06 mg/L EPI Suite v4.10
pKa Results
Acidic/Basic Acidic/Basic Aparrent pKa Value Error
10 A 14.83 0.7
8 A 14.48 0.1
10 A 13.68 0.7
11 MA 12.27 0.7
A = Acidic
B = Basic
MA = Most Acidic
MB = Most Basic
Calculations performed using ACD/PhysChem v 9.14

Authors of this ToxBank wiki page

David Bower, Egon Willighagen, Matthew Clark
Facts about GalactosamineRDF feed
Accepted by ToxBankno  +
Accepted by ToxCastno  +
Equivalent URIThis property is a special property in this wiki.  +,  +,  +, and,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1  +
Has CAS7535-00-4  +
Has ChemSpider Id22576  +
Has InChIInChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1  +
Has Leadscope IdLS-71022  +
Has PubChem CID24154  +
Has SmilesO1[C@@H]([C@@H]([C@@H]([C@H](N)[C@@H]1O)O)O)CO  +
Has categoryHepatotoxic  +
Has imagegalactosamine.png  +
Has pKa7.71  +
Has toxic effectApoptosis  +
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