2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

• ChemBase ID: 58694
• Molecular Formular: C7H14N2O4S
• Molecular Mass: 222.26206
• Monoisotopic Mass: 222.06742794
• SMILES: C(CSCCC(N)C(=O)O)(N)C(=O)O
• Canonical SMILES: NC(C(=O)O)CCSCC(C(=O)O)N
• InChI: InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)
• InChIKey: ILRYLPWNYFXEMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid
• IUPAC Traditional name: cystathionine
• Synonyms: S-(2-Amino-2-carboxyethyl)homocysteine; L-Cystathionine; S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteine; Cystathionine; DL,DL-allo-Cystathionine; S-(2-Amino-2-carboxyethyl)homocysteine; Cystathionine; DL-Allocystathionine; NSC 118379; D,L-Cystathionine

Database IDs

• CAS Number: 535-34-2; 56-88-2
• EC Number: 208-613-7
• MDL Number: MFCD00136759
• PubChem SID: 24892630; 162063457
• PubChem CID: 834
• CHEBI ID: 17755
• CHEMBL: 209241
• Chemspider ID: 811
• KEGG ID: C00542
• MeSH Name: Cystathionine
• Wikipedia Title: Cystathionine

CALCULATED PROPERTIES

• Acid pKa: 1.7937987
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.8184667
• LogD (pH = 7.4): -5.8285646
• Log P: -5.818502
• Molar Refractivity: 51.5689 cm^3
• Polarizability: 20.893393 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Crystalline Solid
• Melting Point: 315-316°C dec.

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... BHMT(635)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - C3633

Other Notes
A mixture of 4 stereoisomers; L-, D-, L-allo- and D-allo-cystathionine.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C3633.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Preparation Note
Prepared by method of Stekol.1

Toronto Research Chemicals - C989495

Intermediate for transsulfuration whereby a mammal transfers the sulfur of methionine via homocysteine to cysteine.

REFERENCES

• Thompson, J.W., et al.: J. Biol. Chem., 266, 17011 (1991)
• Yoshida, Y., et al.: Microbiol., 148, 3961 (1991)
• Jiracek, J., et al.: J. Med. Chem., 49, 3982 (1991)