S-Formylglutathione (YMDB00320)

Identification

YMDB ID

YMDB00320

Name

S-Formylglutathione

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

S-Formylglutathione 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-Formylglutathione exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on S-Formylglutathione.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

S-Formylglutathione
N-(S-(Formyl-N-L-gamma-glutamyl)-L-cysteinyl)glycine
N-(S-(Formyl-N-L-g-glutamyl)-L-cysteinyl)glycine
N-(S-(Formyl-N-L-γ-glutamyl)-L-cysteinyl)glycine
L-gamma-Glutamyl-S-formyl-L-cysteinylglycine
L-γ-Glutamyl-S-formyl-L-cysteinylglycine

CAS number

50409-81-9

Weight

Average: 335.334
Monoisotopic: 335.078720603

InChI Key

FHXAGOICBFGEBF-BQBZGAKWSA-N

InChI

InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

IUPAC Name

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

Traditional IUPAC Name

S-formylglutathione

Chemical Formula

C₁₁H₁₇N₃O₇S

SMILES

[H]OC(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H])C([H])([H])SC([H])=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
S-acylglutathione
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
L-alpha-amino acid
N-acyl-amine
Fatty acyl
Fatty amide
Dicarboxylic acid or derivatives
Fatty acid
Secondary carboxylic acid amide
Amino acid or derivatives
Thiocarboxylic acid ester
Amino acid
Carboxamide group
Carbothioic s-ester
Sulfenyl compound
Carboxylic acid
Thiocarboxylic acid or derivatives
Organosulfur compound
Primary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-acylglutathione (CHEBI:16225 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.62 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-5.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	175.89 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	74.09 m³·mol⁻¹	ChemAxon
Polarizability	31.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Methane metabolism

ec00680

SMPDB Reactions

Not Available

KEGG Reactions

Formaldehyde + NAD + Glutathione ↔ S-Formylglutathione + NADH + hydron

S-Formylglutathione + water ↔ Glutathione + Formic acid + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5291000000-b6c23fa7c47e31aeddcb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-023c-9313500000-1da9e85e107515d2bbe5	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mx-1195000000-93ac994a9ac61ae6c14c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fcc-4890000000-fbee4581354032da3ef0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zos-3920000000-743fa6d73cbb62d84f60	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1159000000-214301d7e8c99ddf96fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-060r-3393000000-78df0617238659fc6300	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9300000000-0f76d8993b5fd4cd5b6b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0329000000-7a800da0a94fe1013f19	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06ss-7791000000-2052b7e618d4e9ecbbe8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01r7-9600000000-07208904e99ff0f33698	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0139000000-01e4c0c1d065ab8b458c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06uu-1961000000-379460e46f591193cd28	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-9500000000-6c89c9382a5e5647ed69	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16225
HMDB ID	HMDB01550
Pubchem Compound ID	488
Kegg ID	C01031
ChemSpider ID	164320
FOODB ID	FDB022685
Wikipedia ID	Not Available
BioCyc ID	CPD-548

Enzymes

Protein Details

1. S-(hydroxymethyl)glutathione dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Oxidizes long-chain alcohols and, in the presence of glutathione, is able to oxidize formaldehyde. Is responsible for yeast resistance to formaldehyde
Gene Name:: SFA1
Uniprot ID:: P32771
Molecular weight:: 41041.69922

Reactions

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

Protein Details

2. S-formylglutathione hydrolase

General function:: Involved in carboxylesterase activity
Specific function:: Serine hydrolase involved in the detoxification of formaldehyde
Gene Name:: Not Available
Uniprot ID:: P40363
Molecular weight:: 33934.0

Reactions

S-formylglutathione + H(2)O → glutathione + formate.
4-methylumbelliferyl acetate + H2O → 4-methylumbelliferone + acetate

Structure for #<Compound:0xa6d822a4>

Enzymes

Reactions

Reactions