L-homocysteine zwitterion
Basic information
- CAS
6027-13-0- Standard SMILES
[NH3+][C@@H](CCS)C(=O)[O-]- InChIKey
FFFHZYDWPBMWHY-VKHMYHEASA-N- Molecular formula
- C4H9NO2S
- Average molar mass
- 135.19 g/mol
- Monoisotopic mass
- 135.0353997
Overview
L-homocysteine zwitterion is an amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-homocysteine; major species at pH 7.3. It has a role as a fundamental metabolite. It is a tautomer of a L-homocysteine.
Names & identifiers
- Preferred name
- L-homocysteine zwitterion
- IUPAC
- (2S)-2-azaniumyl-4-sulfanylbutanoate
- English name
- L-Homocysteine
- Molecular formula
- C4H9NO2S
- Molecular weight
- 135.18
Names & synonyms
L-homocysteine zwitterionCHEBI:58199(S)-2-AMINO-4-MERCAPTOBUTANOIC ACIDHOMO-CYSH-Hcys-OHL-HomocysteinL-Homocysteine(S)-HOMOCYSTEINEL-Homocysteine ,95%Efavirenz Impurity 20S-Methyl-L-homocysteineH-Hcy-OH/L-Homocysteine
Database identifiers
- CAS
6027-13-0- PubChem CID
- 6971015
- ChEBI
CHEBI:58199
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 68.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 80.6
Experimental & physicochemical properties
Solubility148 mg/mL
Melting Point232 - 233 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 232 °C · 232°C
- Boiling point
- 299.7 · 299.7±35.0 °C(Predicted)
- Density
- 1.149 · 1.149 (estimate)
- refractive index
- 1.548 · 1.5480 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Acid (Sparingly, Heated, Sonicated), Water (Slightly, Heated)
- pka
- 2.24 · 2.24±0.10(Predicted)
- form
- solid
- color
- White to Off-White
- optical activity
- 25.5 · [α]/D 25.5±1.5°, c = 1 in 1 M HCl
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 29309090
- Toxicity
- mouse,LD50,intraperitoneal,> 1082mg/kg (1082mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1419, 1974.
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H413-H372
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Applications
UsesL-homocysteine has been used as a supplement in cell culture media.
UsesL-Homocysteine is the hydrolysis product of adenosine (A280400), a purine nucleoside. Metabolic fate of L-Homocysteine is converted back to L-Methionine( M260440) via tetrahydrofolate.
General DescriptionL-homocysteine is used to diagnose homocystinuria.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Homocysteine with L configuration.
Suppliers
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