Thiodigalactoside

Identification

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Name
Thiodigalactoside
Accession Number
DB04396  (EXPT03030)
Type
Small Molecule
Groups
Experimental
Description

Thiodigalactoside is a solid. This compound belongs to the dihexoses. These are disaccharides containing two hexose carbohydrates. This medication is known to target galectin-1, heat-labile enterotoxin b chain, neurocan core protein, and lactose permease.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
51555-87-4
Weight
Average: 358.362
Monoisotopic: 358.093367614
Chemical Formula
C12H22O10S
InChI Key
SYKYBMOFPMXDRQ-ZFDCCPEWSA-N
InChI
InChI=1S/C12H22O10S/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5+,6+,7+,8+,9-,10-,11+,12+/m1/s1
IUPAC Name
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@@]([H])(S[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat-labile enterotoxin B chainNot AvailableEscherichia coli
ULactose permeaseNot AvailableEscherichia coli (strain K12)
UNeurocan core proteinNot AvailableHumans
UGalectin-1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
119138
PubChem Substance
46509001
ChemSpider
106443
BindingDB
50077225
ChEMBL
CHEMBL52011
HET
TDG
PDB Entries
1a78 / 1lt5 / 1muq / 1pv7 / 3oyw / 4jc1 / 4oaa

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility452.0 mg/mLALOGPS
logP-3ALOGPS
logP-4.4ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area180.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.7 m3·mol-1ChemAxon
Polarizability32.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7633
Blood Brain Barrier+0.595
Caco-2 permeable-0.7913
P-glycoprotein substrateNon-substrate0.607
P-glycoprotein inhibitor INon-inhibitor0.8256
P-glycoprotein inhibitor IINon-inhibitor0.9501
Renal organic cation transporterNon-inhibitor0.8033
CYP450 2C9 substrateNon-substrate0.809
CYP450 2D6 substrateNon-substrate0.8549
CYP450 3A4 substrateNon-substrate0.6553
CYP450 1A2 substrateNon-inhibitor0.8748
CYP450 2C9 inhibitorNon-inhibitor0.8715
CYP450 2D6 inhibitorNon-inhibitor0.8968
CYP450 2C19 inhibitorNon-inhibitor0.7814
CYP450 3A4 inhibitorNon-inhibitor0.9005
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7478
Ames testNon AMES toxic0.6586
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.9253
Rat acute toxicity1.6872 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9707
hERG inhibition (predictor II)Non-inhibitor0.8492
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Thioglycosides
Alternative Parents
Thio-linked disaccharides / Oxanes / Monothioacetals / Secondary alcohols / Sulfenyl compounds / Polyols / Oxacyclic compounds / Primary alcohols / Hydrocarbon derivatives
Substituents
Thio-linked disaccharide / S-glycosyl compound / Disaccharide / Oxane / Monothioacetal / Secondary alcohol / Oxacycle / Organoheterocyclic compound / Sulfenyl compound / Polyol
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Not Available
Specific Function
The biological activity of the toxin is produced by the A chain, which activates intracellular adenyl cyclase.
Gene Name
eltB
Uniprot ID
P32890
Uniprot Name
Heat-labile enterotoxin B chain
Molecular Weight
14133.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Sugar:proton symporter activity
Specific Function
Responsible for transport of beta-galactosides into the cell, with the concomitant import of a proton (symport system).
Gene Name
lacY
Uniprot ID
P02920
Uniprot Name
Lactose permease
Molecular Weight
46502.76 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Hyaluronic acid binding
Specific Function
May modulate neuronal adhesion and neurite growth during development by binding to neural cell adhesion molecules (NG-CAM and N-CAM). Chondroitin sulfate proteoglycan; binds to hyaluronic acid.
Gene Name
NCAN
Uniprot ID
O14594
Uniprot Name
Neurocan core protein
Molecular Weight
143092.14 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Details
4. Galectin-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Signal transducer activity
Specific Function
Lectin that binds beta-galactoside and a wide array of complex carbohydrates. Plays a role in regulating apoptosis, cell proliferation and cell differentiation. Inhibits CD45 protein phosphatase ac...
Gene Name
LGALS1
Uniprot ID
P09382
Uniprot Name
Galectin-1
Molecular Weight
14715.57 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 06:05