(2S)-2-amino-5-carbamimidamidopentanoic acid; (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 164821
• Molecular Formular: C21H33N5O5S2
• Molecular Mass: 499.64722
• Monoisotopic Mass: 499.19231118
• SMILES: C1[C@H](C[C@H](N1C(=O)[C@@H](CS)C)C(=O)O)Sc1ccccc1.NC(=N)NCCC[C@H](N)C(=O)O
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)O)N.SC[C@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)Sc1ccccc1)C
• InChI: InChI=1S/C15H19NO3S2.C6H14N4O2/c1-10(9-20)14(17)16-8-12(7-13(16)15(18)19)21-11-5-3-2-4-6-11;7-4(5(11)12)2-1-3-10-6(8)9/h2-6,10,12-13,20H,7-9H2,1H3,(H,18,19);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t10-,12+,13+;4-/m10/s1
• InChIKey: OSKWTWSFSUAPKP-KQUFBQNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-carbamimidamidopentanoic acid; (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid; L-arginine
• Synonyms: 3-Chloro-10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine Hydrochloride; 3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine Hydrochloride; Chlorimipramine Hydrochloride; Anafranil; Clomicalm; Clomipramine Hydrochloride

Database IDs

• CAS Number: 17321-77-6
• PubChem SID: 162258955
• PubChem CID: 11954366

CALCULATED PROPERTIES

• Acid pKa: 3.911476
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.81910414
• LogD (pH = 7.4): -0.79468316
• Log P: 2.413754
• Molar Refractivity: 86.6838 cm^3
• Polarizability: 34.00856 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Water
• Apperance: Off-White Solid
• Melting Point: 189-190°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C587050

Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent.

REFERENCES

• Peters, M.D., et al.: Clin. Pharm., 9, 165 (1990)
• Adamczyk, M., et al.: Ther. Drug Monit., 17, 371 (1990)
• Poolsup, N., et al.: J. Clin. Pharm. Ther., 25, 197 (1990)
• Bose, D., et al.: J. Pharmacol. Toxicol. Methods, 52, 323 (1990)