2-amino-5-{[(methylsulfanyl)methanimidoyl]amino}pentanoic acid

• ChemBase ID: 174360
• Molecular Formular: C7H15N3O2S
• Molecular Mass: 205.2779
• Monoisotopic Mass: 205.08849774
• SMILES: CSC(=N)NCCCC(N)C(=O)O
• Canonical SMILES: CSC(=N)NCCCC(C(=O)O)N
• InChI: InChI=1S/C7H15N3O2S/c1-13-7(9)10-4-2-3-5(8)6(11)12/h5H,2-4,8H2,1H3,(H2,9,10)(H,11,12)
• InChIKey: NGVMVBQRKZPFLB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-{[(methylsulfanyl)methanimidoyl]amino}pentanoic acid
• IUPAC Traditional name: 2-amino-5-{[(methylsulfanyl)methanimidoyl]amino}pentanoic acid
• Synonyms: S-Methyl-L-thiocitrulline Hydrochloride

Database IDs

• CAS Number: 156719-39-0
• PubChem SID: 164230270
• PubChem CID: 5148969

CALCULATED PROPERTIES

• Acid pKa: 2.3376422
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.434144
• LogD (pH = 7.4): -3.2797835
• Log P: -1.6624365
• Molar Refractivity: 63.0436 cm^3
• Polarizability: 20.657053 Å^3
• Polar Surface Area: 99.2 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Desiccate and Store at -20°C

DETAILS

Toronto Research Chemicals - M330750

S-Methyl-L-thiocitrulline is a new potent nitric oxide synthase inhibitor for treatment of cancer.

REFERENCES

• Narayanan, et al.: J. Med. Chem., 37, 885 (1994)
• Narayanan, et al.: J. Biol. Chem., 270, 11103 (1994)