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Hydrogen sulfide (YMDB00653)

Identification
YMDB IDYMDB00653
NameHydrogen sulfide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHydrogen sulfide (H2S) is a powerful aroma compound largely produced by yeast during fermentation. Its occurrence in wines and other fermented beverages has been associated with off-odors described as rotten egg and/or sewage. In wine fermentations, H2S is largely formed by reduction of exogenous sulfate during the biosynthesis of the sulfur-containing amino acids cysteine and methionine. Sulfite, which is commonly added to grape musts as an antioxidant and antimicrobial agent, can also enter the cell and become a source of H2S, after reduction by sulfite reductase. [Biocyc SO4ASSIM-PWY] [PMID: 20668912]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • acide sulfhydrique
  • Dihydrogen disulfide
  • Dihydrogen monosulfide
  • Dihydrogen sulfide
  • H2S
  • Hepatate
  • Hepatic acid
  • Hepatic gas
  • Hydrogen monosulfide
  • Hydrogen sulfide
  • Hydrogen sulfide (H2S)
  • hydrogen sulphide
  • Hydrogen-sulfide
  • Hydrogen-sulphide-
  • Hydrogene sulfure
  • Hydrosulfurate
  • Hydrosulfuric acid
  • Idrogeno solforato
  • Schwefelwasserstoff
  • Sewer gas
  • Siarkowodor
  • Sour gas
  • Stink damp
  • Sulfide
  • Sulfur hydride
  • Sulfur hydroxide
  • Sulfureted hydrogen
  • Sulfuretted hydrogen
  • [SH2]
  • Sulfure d'hydrogene
  • Acide sulphhydrique
  • Dihydrogen monosulphide
  • Dihydrogen sulphide
  • Hydrogen monosulphide
  • Hydrogen-sulphide
  • Hydrogene sulphure
  • HYDROsulfate
  • HYDROsulphate
  • HYDROsulphuric acid
  • Sulphide
  • Sulphure d'hydrogene
  • Zwavelwaterstof
  • Sulfide, hydrogen
  • Hydrogen sulfide (H2(SX))
  • Hydrogen sulfide (H2S2)
  • Hydrogen sulfide (H2S3)
CAS number7783-06-4
WeightAverage: 34.081
Monoisotopic: 33.987720754
InChI KeyRWSOTUBLDIXVET-UHFFFAOYSA-N
InChIInChI=1S/H2S/h1H2
IUPAC Namehydrogen sulfide
Traditional IUPAC Namehydrogen sulfide
Chemical FormulaH2S
SMILES[H]S[H]
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as other non-metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassOther non-metal organides
Sub ClassOther non-metal sulfides
Direct ParentOther non-metal sulfides
Alternative Parents
Substituents
  • Other non-metal sulfide
  • Inorganic sulfide
Molecular FrameworkNot Available
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-85.49 °C
Experimental Properties
PropertyValueReference
Water Solubility3.74 mg/mL at 21 oC [VENABLE,CS & FUWA,T (1922)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
logP-0.038ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity7.36 m³·mol⁻¹ChemAxon
Polarizability3.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
EggFDB030910
RottenFDB030910
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Acetylhomoserine + Hydrogen sulfide → Acetic acid + hydron + Homocysteine
L-Cysteine → Hydrogen sulfide + hydron + 2-aminoprop-2-enoate
Sulfite + NADPH + hydron → water + NADP + Hydrogen sulfide
Hydrogen sulfide + O-acetyl-L-serine ↔ L-Cysteine + Acetic acid + hydron
L-Cysteine → hydron + Hydrogen sulfide + 2-Aminoacrylic acid
KEGG Reactions
O-acetyl-L-serine + Hydrogen sulfide → Acetic acid + hydron + L-Cysteine
O-Acetyl-L-homoserine + Hydrogen sulfide → L-Homocysteine + Acetic acid + hydron
NADP + water + Hydrogen sulfide ↔ hydron + Sulfite + NADPH
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-1900000000-447434090a2b915c1731JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1900000000-447434090a2b915c1731JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-3a89a2549173c5c1687fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-2d63abb89fd699a31707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-05710009cb2405db27bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-942ac689538269d6ca7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-942ac689538269d6ca7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-942ac689538269d6ca7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-db65f6d26b49c6300706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-db65f6d26b49c6300706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-db65f6d26b49c6300706JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-5373be1d46feb66d09a8JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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
  • Spiropoulos, A., Bisson, L. F. (2000). "MET17 and hydrogen sulfide formation in Saccharomyces cerevisiae." Appl Environ Microbiol 66:4421-4426.11010893
  • Mulet, J. M., Alemany, B., Ros, R., Calvete, J. J., Serrano, R. (2004). "Expression of a plant serine O-acetyltransferase in Saccharomyces cerevisiae confers osmotic tolerance and creates an alternative pathway for cysteine biosynthesis." Yeast 21:303-312.15042590
  • Hansen, J., Muldbjerg, M., Cherest, H., Surdin-Kerjan, Y. (1997). "Siroheme biosynthesis in Saccharomyces cerevisiae requires the products of both the MET1 and MET8 genes." FEBS Lett 401:20-24.9003798
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16136
HMDB IDHMDB03276
Pubchem Compound ID402
Kegg IDC00283
ChemSpider ID391
FOODB IDFDB030910
WikipediaHydrogen_sulfide
BioCyc IDHS

Enzymes

Protein Details
1. Putative cysteine synthase
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
Not Available
Uniprot ID:
P53206
Molecular weight:
42800.5
Reactions
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
Protein Details
2. Protein MET17
General function:
Involved in pyridoxal phosphate binding
Specific function:
Transforms O-acetylhomoserine into homocysteine and O- acetylserine into cysteine
Gene Name:
MET17
Uniprot ID:
P06106
Molecular weight:
48671.39844
Reactions
O-acetyl-L-homoserine + methanethiol → L-methionine + acetate.
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
Protein Details
3. Cystathionine gamma-lyase
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Gene Name:
CYS3
Uniprot ID:
P31373
Molecular weight:
42541.69922
Reactions
L-cystathionine + H(2)O → L-cysteine + NH(3) + 2-oxobutanoate.
Protein Details
4. Sulfite reductase [NADPH] subunit beta
General function:
Involved in iron ion binding
Specific function:
Catalyzes the reduction of sulfite to sulfide, one of several activities required for the biosynthesis of L-cysteine from sulfate
Gene Name:
ECM17
Uniprot ID:
P47169
Molecular weight:
161218.0
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O → sulfite + 3 NADPH.
Protein Details
5. Sulfite reductase [NADPH] flavoprotein component
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L-cysteine from sulfate
Gene Name:
MET10
Uniprot ID:
P39692
Molecular weight:
114827.0
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O → sulfite + 3 NADPH.