Showing Compound Card for S-Hydroxymethylglutathione (CDB004971)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:55:54 UTC
Updated at2020-11-18 16:39:08 UTC
CannabisDB IDCDB004971
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameS-Hydroxymethylglutathione
DescriptionS-(Hydroxymethyl)glutathione, also known as sergsh, 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. S-(Hydroxymethyl)glutathione is a very strong basic compound (based on its pKa). An S-substituted glutathione that is glutathione in which the mercapto hydrogen has been replaced by a hydroxymethyl group. S-(Hydroxymethyl)glutathione exists in all living species, ranging from bacteria to humans. S-Hydroxymethylglutathione is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACIDChEBI, HMDB
S-HydroxymethylglutathioneChEBI
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrateGenerator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrateGenerator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acidGenerator, HMDB
S-Hydroxymethyl-glutathioneHMDB
SerGSHMeSH, HMDB
Formaldehyde-glutathione thiohemiacetalHMDB
Glutathione-formaldehyde thiohemiacetalHMDB
L-gamma-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycineHMDB
L-γ-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycineHMDB
S-(Hydroxymethyl)glutathioneHMDB
Chemical FormulaC11H19N3O7S
Average Molecular Weight337.35
Monoisotopic Molecular Weight337.0944
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
Traditional NameS-hydroxymethylglutathione
CAS Registry Number32260-87-0
SMILES
N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1
InChI KeyPIUSLWSYOYFRFR-BQBZGAKWSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Sulfenyl compound
  • Carboxylic acid
  • Organopnictogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.2ALOGPS
logP-5.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area179.05 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity75.2 m³·mol⁻¹ChemAxon
Polarizability32.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Hydroxymethylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01po-6291000000-700a78b68cd3c72dace0Spectrum
Predicted GC-MSS-Hydroxymethylglutathione, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ukl-9410370000-758e7d3d20ef5e803fa9Spectrum
Predicted GC-MSS-Hydroxymethylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-0195000000-0fb852c5aa71ebfacbc32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0570-4690000000-74c4fbcadf9e75cea5e62015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4920000000-a75d217a2989134725ab2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-5089000000-0963b985ed393a77403b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-5393000000-80626db3d68b3e84d33f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-9200000000-c770bc62700bd5b4872c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0029000000-9285be543171793a7f612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-1941000000-3b0ed9e0505deb83df542021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9400000000-cdcded7632edf6274abf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-0193000000-b9ae6fff6991f7a74ac12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-9440000000-4e976999daadff083f1c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9400000000-49e525bdebda32941d942021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alcohol dehydrogenase class-3ADH54q23P11766 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Alcohol dehydrogenase class-3ADH54q23P11766 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0004662
DrugBank IDDB04153
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023393
KNApSAcK IDNot Available
Chemspider ID394301
KEGG Compound IDC14180
BioCyc IDS-HYDROXYMETHYLGLUTATHIONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7068
PubChem Compound447123
PDB IDAHE
ChEBI ID48926
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Alcohol dehydrogenase class-3
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945