L-Cystathionine
Basic information
- CAS
56-88-2- Standard SMILES
N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O- InChIKey
ILRYLPWNYFXEMH-WHFBIAKZSA-N- Molecular formula
- C7H14N2O4S
- Average molar mass
- 222.26 g/mol
- Monoisotopic mass
- 222.06742811
Overview
L-cystathionine is a modified amino acid generated by enzymic means from L-homocysteine and L-serine. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a tautomer of a L-cystathionine dizwitterion.
Names & identifiers
- Preferred name
- L-Cystathionine
- IUPAC
- (2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
- English name
- L-Cystathionine
- Molecular formula
- C7H14N2O4S
- Molecular weight
- 222.26
Names & synonyms
L-cystathionine56-88-2L-(+)-CystathionineCystathionine, L-(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid375YFJ481OCHEBI:17482(2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acidButanoic acid, 2-amino-4-((2-amino-2-carboxyethyl)thio)-, (R-(R*,S*))-(2S)-2-amino-4-((2R)-2-amino-2-carboxyethyl)sulfanylbutanoic acid(2S)-2-amino-4-(((2R)-2-amino-2-carboxyethyl)sulfanyl)butanoic acidButanoic acid, 2-amino-4-[(2-amino-2-carboxyethyl)thio]-, [R-(R*,S*)]-
Show more names
L(+)CYSTATHIONINEL-Cystathionine (P)L-Cystathionine StandardL-CYSTATHIONINE, >= 98% (TLC)CYSTATHIONINE, L-(DS)(REQUEST QUOTE)(2R,7S)-2,7-Diamino-4-thiaoctanedioic acid[R]-S-[2-AMINO-2-CARBOXYETHYL]-L-HOMOCYSTEINE
(2S)-2-azaniumyl-4-((2R)-2-azaniumyl-2-carboxylatoethyl)sulfanylbutanoateRefChem:1088149200-295-8(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteineS-[(2R)-2-amino-2-carboxyethyl]-L-HomocysteineCystathionine, L- (8CI)L-Homocysteine, S-(2-amino-2-carboxyethyl)-, (R)-(2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid
Properties
Computed structural properties
- XLogP
- -6
- Topological polar surface area
- 152 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 212
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
Solubility22 mg/mL
Melting Point312 °C
Physical Description
Solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
147 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
144.41 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
142.1 Ų [M-H]-
Physicochemical properties
- Melting point
- 312 · 312
- alpha
- 20 · D20 +23.7° (1N HCl)
- Density
- 1.43 · 1.430±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Acid (Slightly)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29309090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
UsesAmino acid; [Merck Index]
Applications
DescriptionL-(+)-Cystathionine is a dipeptide formed by serine and homocysteine. Transsulfuration of methionine yields homocysteine, which combines with serine to form this precursor of cysteine. L-(+)-Cystathionine is largely expressed in the mammalian brain and deficiency can indicate the presence of metabolic disorders such as cystathioninuria.
UsesIntermediate in transsulfuration whereby the mammal transfers the sulfur of methionine via homocysteine to cysteine
UsesL-Cystathionine has been used in ultra-performance liquid chromatography for the validation of cystathionine and the correlation of its abundance with vertebrate metamorphosis. It has also been used as an inhibitor of sinusoidal GSH (glutathione) carrier to signify that thiol redox state imbalance is associated with the modulation of autophagy in carcinoma cells.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: L-cystathionine is a modified amino acid generated by enzymic means from L-homocysteine and L-serine. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a tautomer of a L-cystathionine dizwitterion.
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