1-[3-(acetylsulfanyl)propanoyl]-6-methylpiperidine-2-carboxylic acid

• ChemBase ID: 53542
• Molecular Formular: C12H19NO4S
• Molecular Mass: 273.34856
• Monoisotopic Mass: 273.10347909
• SMILES: N1(C(=O)CCSC(=O)C)C(C(=O)O)CCCC1C
• Canonical SMILES: CC(=O)SCCC(=O)N1C(C)CCCC1C(=O)O
• InChI: InChI=1S/C12H19NO4S/c1-8-4-3-5-10(12(16)17)13(8)11(15)6-7-18-9(2)14/h8,10H,3-7H2,1-2H3,(H,16,17)
• InChIKey: JHFOAISYWJRTIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(acetylsulfanyl)propanoyl]-6-methylpiperidine-2-carboxylic acid
• IUPAC Traditional name: 1-[3-(acetylsulfanyl)propanoyl]-6-methylpiperidine-2-carboxylic acid
• Synonyms: 1-[3-(Acetylsulfanyl)propanoyl]-6-methyl-2-piperidinecarboxylic acid; Methiapril; Metiopril; Metiapril; 1-(3-(acetylthio)propanoyl)-6-methylpiperidine-2-carboxylic acid

Database IDs

• CAS Number: 169551-84-2
• MDL Number: MFCD00564080
• PubChem SID: 162058305
• PubChem CID: 2772126

CALCULATED PROPERTIES

• Acid pKa: 3.8374238
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7803813
• LogD (pH = 7.4): -2.3591132
• Log P: 0.8856862
• Molar Refractivity: 68.548 cm^3
• Polarizability: 27.079384 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: ACE inhibitor; Angiotensin antagonist; Vasodilators

Product Information

• Description: Diastereomers
• Application(s): Hypotensive

DETAILS

InterBioScreen - BB_SC-1521

Diastereomers

REFERENCES

• Can.J.Physiol.Pharmacol. (72, Suppl. 1, 138, 1994) Experimental and clinical study of new antihypertensive drug metiapril.