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27025-41-8 molecular structure
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(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

ChemBase ID: 127585
Molecular Formular: C20H32N6O12S2
Molecular Mass: 612.63108
Monoisotopic Mass: 612.15196249
SMILES and InChIs

SMILES:
C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
Canonical SMILES:
O=C(N[C@H](C(=O)NCC(=O)O)CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
InChI:
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
InChIKey:
YPZRWBKMTBYPTK-BJDJZHNGSA-N

Cite this record

CBID:127585 http://www.chembase.cn/molecule-127585.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
IUPAC Traditional name
glutathione disulfide
Synonyms
L-Glutathione oxidized
Glutathiol
(-)-Glutathione, oxidized
Glutathione disulfide
GSSG
L-Glutathione oxidized
N,N'-[Dithiobis[1-[(carboxymethyl)carbamoyl]ethylene]]diglutamine
Glutathione Disulphide
Glutathione Oxidized
Glutathione-S-S-glutathione
Glutathione-SSG
Glutathone Disulfide
Oxidized L-Glutathione
Oxidized Glutathione
Oxiglutatione
L-谷胱甘肽(氧化型)
(-)-谷胱甘肽(氧化型)
氧化谷胱甘肽
L-谷胱甘肽(氧化型)
CAS Number
27025-41-8
EC Number
248-170-7
MDL Number
MFCD00063106
Beilstein Number
1718700
PubChem SID
24873118
24873116
24895168
24895265
24895174
24849044
162221904
PubChem CID
65359
CHEMBL
1372
Chemspider ID
58835
Wikipedia Title
Glutathione_disulfide

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.438368  H Acceptors 14 
H Donor 10  LogD (pH = 5.5) -13.715199 
LogD (pH = 7.4) -16.599508  Log P -10.109055 
Molar Refractivity 136.6544 cm3 Polarizability 54.28691 Å3
Polar Surface Area 317.64 Å2 Rotatable Bonds 21 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble expand Show data source
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble10 mg/mL, clear, colorless expand Show data source
Water expand Show data source
Apperance
lyophilized powder expand Show data source
powder expand Show data source
White Solid expand Show data source
Melting Point
178 °C (dec.)(lit.) expand Show data source
180-182°C expand Show data source
Optical Rotation
[α]20/D -100±4°, c = 2% in H2O expand Show data source
[α]20/D -100±7°, c = 2% in H2O expand Show data source
[α]20/D -92.0 to -106.0°, c = 2% in H2O expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
~98% expand Show data source
≥95% (HPLC) expand Show data source
≥98% expand Show data source
≥98% (HPLC) expand Show data source
≥99.0% (sum of enantiomers, HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Ignition Residue
≤0.5% expand Show data source
Impurities
≤0.005% Phosphorus (P) expand Show data source
≤0.1% Insoluble matter expand Show data source
≤6% ethanol expand Show data source
≤6% water expand Show data source
≤6% water (Karl Fischer) expand Show data source
Ethanol, free expand Show data source
Cation Traces
Al: ≤0.0005% expand Show data source
Ca: ≤0.001% expand Show data source
Ca: ≤50 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤0.0005% expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤0.0005% expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤0.005% expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤0.0005% expand Show data source
Mg: ≤10 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤0.005% expand Show data source
Na: ≤500 mg/kg expand Show data source
NH4+: ≤0.05% expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤0.001% expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤0.0005% expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤0.05% expand Show data source
sulfate (SO42-): ≤0.05% expand Show data source
Purified By
crystallization expand Show data source
Quality Level
PREMIUM expand Show data source
Linear Formula
[HO2CCH(NH2)CH2CH2CONHCH(CONHCH2CO2H)CH2S-]2 expand Show data source
Empirical Formula (Hill Notation)
C20H32N6O12S2 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - G4376 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Sigma Aldrich - 49740 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Other Notes
Review1
Sigma Aldrich - G4501 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Sigma Aldrich - G9027 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Sigma Aldrich - G6654 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Sigma Aldrich - 150568 external link
Packaging
5 g in glass bottle
500 mg in glass bottle
Application
Hydrogen acceptor in the enzymic determination of NADP and NADPH.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 150568.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - 49741 external link
Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Toronto Research Chemicals - G597970 external link
A biomarker for fatty liver disease.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Tsou, P.-S., et al.: J. Pharmacol. Exp. Ther., 329, 649 (2009)
  • • Yu, Y-C., et al.: J. Neurosci. Res., 87, 1884 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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