S-Hexylglutathione

Identification

Name
S-Hexylglutathione
Accession Number
DB04132  (EXPT01664)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
M73SNN908F
CAS number
Not Available
Weight
Average: 391.483
Monoisotopic: 391.177706365
Chemical Formula
C16H29N3O6S
InChI Key
HXJDWCWJDCOHDG-RYUDHWBXSA-N
InChI
InChI=1S/C16H29N3O6S/c1-2-3-4-5-8-26-10-12(15(23)18-9-14(21)22)19-13(20)7-6-11(17)16(24)25/h11-12H,2-10,17H2,1H3,(H,18,23)(H,19,20)(H,21,22)(H,24,25)/t11-,12-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-(hexylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES
[H][[email protected]](N)(CCC(O)=N[[email protected]@]([H])(CSCCCCCC)C(O)=NCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULactoylglutathione lyaseNot AvailableHuman
UGlutathione S-transferase Mu 4Not AvailableHuman
UGlutathione S-transferase PNot AvailableHuman
UGlutathione S-transferaseNot AvailablePlasmodium falciparum
UGlutathione S-transferase A1Not AvailableHuman
UGlutathione S-transferase theta-2Not AvailableHuman
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
KEGG Compound
C02886
PubChem Compound
97536
PubChem Substance
46505872
ChemSpider
88033
BindingDB
50095998
ChEBI
27704
ChEMBL
CHEMBL345292
Therapeutic Targets Database
DNC001323
HET
LEE
PDB Entries
1gss

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 Solubility0.0915 mg/mLALOGPS
logP-1ALOGPS
logP-0.76ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.07ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.8 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity97.93 m3·mol-1ChemAxon
Polarizability42.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6561
Blood Brain Barrier+0.6211
Caco-2 permeable-0.6298
P-glycoprotein substrateSubstrate0.7585
P-glycoprotein inhibitor INon-inhibitor0.8808
P-glycoprotein inhibitor IINon-inhibitor0.9867
Renal organic cation transporterNon-inhibitor0.9559
CYP450 2C9 substrateNon-substrate0.836
CYP450 2D6 substrateNon-substrate0.7854
CYP450 3A4 substrateNon-substrate0.7014
CYP450 1A2 substrateNon-inhibitor0.8944
CYP450 2C9 inhibitorNon-inhibitor0.8953
CYP450 2D6 inhibitorNon-inhibitor0.9319
CYP450 2C19 inhibitorNon-inhibitor0.8761
CYP450 3A4 inhibitorNon-inhibitor0.9484
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9906
Ames testNon AMES toxic0.8273
CarcinogenicityNon-carcinogens0.9114
BiodegradationReady biodegradable0.7272
Rat acute toxicity2.1333 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9668
hERG inhibition (predictor II)Non-inhibitor0.9233
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 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
MS/MS Spectrum - , negativeLC-MS/MSsplash10-002f-1910000000-0fe3758786a3253107f3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0920000000-87172884f1e3fc7ddcd1

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Glutamine and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / N-acyl amines / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides
show 9 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Alpha-amino acid amide / Cysteine or derivatives / Alpha-amino acid / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives
show 27 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glutathione derivative (CHEBI:27704)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B. Requ...
Gene Name
GLO1
Uniprot ID
Q04760
Uniprot Name
Lactoylglutathione lyase
Molecular Weight
20777.515 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
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name
GSTM4
Uniprot ID
Q03013
Uniprot Name
Glutathione S-transferase Mu 4
Molecular Weight
25561.095 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 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]
Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May also function as a storage protein or ligandin for parasitotoxic ferriprotoporphyrin I...
Gene Name
GST
Uniprot ID
Q8MU52
Uniprot Name
Glutathione S-transferase
Molecular Weight
24788.9 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name
GSTT2
Uniprot ID
P0CG29
Uniprot Name
Glutathione S-transferase theta-2
Molecular Weight
27505.775 Da
References
  1. 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:23