ECMDB: S-(Hydroxymethyl)glutathione (ECMDB04662) (M2MDB000659)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (2)XML

Proteins (204)

Record Information

Version

2.0

Creation Date

2012-05-31 14:07:45 -0600

Update Date

2015-06-03 15:54:50 -0600

Secondary Accession Numbers

ECMDB04662

Identification

Name:

S-(Hydroxymethyl)glutathione

Description

S-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Glycine, N-(N-L-γ-S-(hydroxymethyl)-L-cysteinyl)-
GS-CH2-OH
GS-CH₂-OH
HM-GSH
HMGSH
Hydroxymethylglutathione
N-(N-L-g-S-(Hydroxymethyl)-L-cysteinyl)-glycine
N-(N-L-gamma-S-(Hydroxymethyl)-L-cysteinyl)-Glycine
N-(N-L-γ-S-(Hydroxymethyl)-L-cysteinyl)-glycine
S-Hydroxymethyl-glutathione
S-Hydroxymethylglutathione

Chemical Formula:

C₁₁H₁₉N₃O₇S

Weight:

Average: 337.349
Monoisotopic: 337.094370667

InChI Key:

PIUSLWSYOYFRFR-BQBZGAKWSA-N

InChI:

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

CAS number:

32260-87-0

IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid

Traditional IUPAC Name:

S-hydroxymethylglutathione

SMILES:

N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O

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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:48926 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.27 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-5.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	75.2 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

S-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADH
Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione
S-(Hydroxymethyl)glutathione <> Formaldehyde + Glutathione
NAD(P)<sup>+</sup> + S-(Hydroxymethyl)glutathione <> NAD(P)H + S-Formylglutathione + Hydrogen ion
S-(Hydroxymethyl)glutathione + NAD(P)(+) > S-Formylglutathione + NAD(P)H
S-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ion

SMPDB Pathways:

Not Available

KEGG Pathways:

Glycolysis / Gluconeogenesis ec00010
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

formaldehyde oxidation II (glutathione-dependent) PWY-1801

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01po-6291000000-700a78b68cd3c72dace0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ukl-9410370000-758e7d3d20ef5e803fa9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00du-0195000000-0fb852c5aa71ebfacbc3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0570-4690000000-74c4fbcadf9e75cea5e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4920000000-a75d217a2989134725ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-5089000000-0963b985ed393a77403b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05di-5393000000-80626db3d68b3e84d33f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-9200000000-c770bc62700bd5b4872c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0029000000-9285be543171793a7f61	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-1941000000-3b0ed9e0505deb83df54	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9400000000-cdcded7632edf6274abf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05g0-0193000000-b9ae6fff6991f7a74ac1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-9440000000-4e976999daadff083f1c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9400000000-49e525bdebda32941d94	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Danielsson O, Shafqat J, Estonius M, el-Ahmad M, Jornvall H: Isozyme multiplicity with anomalous dimer patterns in a class III alcohol dehydrogenase. Effects on the activity and quaternary structure of residue exchanges at "nonfunctional" sites in a native protein. Biochemistry. 1996 Nov 19;35(46):14561-8. Pubmed: 8931553
Gutheil, W. G., Holmquist, B., Vallee, B. L. (1992). "Purification, characterization, and partial sequence of the glutathione-dependent formaldehyde dehydrogenase from Escherichia coli: a class III alcohol dehydrogenase." Biochemistry 31:475-481. Pubmed: 1731906
Holmquist B, Moulis JM, Engeland K, Vallee BL: Role of arginine 115 in fatty acid activation and formaldehyde dehydrogenase activity of human class III alcohol dehydrogenase. Biochemistry. 1993 May 18;32(19):5139-44. Pubmed: 8494891
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Koivusalo M, Baumann M, Uotila L: Evidence for the identity of glutathione-dependent formaldehyde dehydrogenase and class III alcohol dehydrogenase. FEBS Lett. 1989 Oct 23;257(1):105-9. Pubmed: 2806555
Lee SL, Wang MF, Lee AI, Yin SJ: The metabolic role of human ADH3 functioning as ethanol dehydrogenase. FEBS Lett. 2003 Jun 5;544(1-3):143-7. Pubmed: 12782305
Sanghani PC, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structural changes associated with ternary complex formation. Biochemistry. 2002 Dec 24;41(51):15189-94. Pubmed: 12484756
Sanghani PC, Stone CL, Ray BD, Pindel EV, Hurley TD, Bosron WF: Kinetic mechanism of human glutathione-dependent formaldehyde dehydrogenase. Biochemistry. 2000 Sep 5;39(35):10720-9. Pubmed: 10978156
Yang ZN, Bosron WF, Hurley TD: Structure of human chi chi alcohol dehydrogenase: a glutathione-dependent formaldehyde dehydrogenase. J Mol Biol. 1997 Jan 24;265(3):330-43. Pubmed: 9018047

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	48926
HMDB ID	HMDB04662
Pubchem Compound ID	447123
Kegg ID	C14180
ChemSpider ID	394301
Wikipedia ID	Not Available
BioCyc ID	S-HYDROXYMETHYLGLUTATHIONE
EcoCyc ID	S-HYDROXYMETHYLGLUTATHIONE
Ligand Expo	AHE

Enzymes

Protein Details

1. S-(hydroxymethyl)glutathione dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:: frmA
Uniprot ID:: P25437
Molecular weight:: 39359

Reactions

S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.

Protein Details

2. Oligopeptide transport system permease protein oppB

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:: oppB
Uniprot ID:: P0AFH2
Molecular weight:: 33443

Protein Details

3. Oligopeptide transport system permease protein oppC

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:: oppC
Uniprot ID:: P0AFH6
Molecular weight:: 33022

Transporters

Protein Details

1. Oligopeptide transport system permease protein oppB

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:: oppB
Uniprot ID:: P0AFH2
Molecular weight:: 33443

Protein Details

2. Oligopeptide transport system permease protein oppC

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:: oppC
Uniprot ID:: P0AFH6
Molecular weight:: 33022

S-(Hydroxymethyl)glutathione (ECMDB04662) (M2MDB000659)

Structure for #<Compound:0xae26f0bc>

Enzymes

Reactions

Transporters