(3S,3aS)-1-methanesulfonyl-4-[4-(piperidin-1-yl)but-2-enoyl]-3-(propan-2-yl)-octahydropyrrolo[3,2-b]pyrrol-2-one hydrochloride

• ChemBase ID: 154269
• Molecular Formular: C19H32ClN3O4S
• Molecular Mass: 433.99308
• Monoisotopic Mass: 433.1802052
• SMILES: CC(C)[C@H]1[C@H]2C(CCN2C(=O)/C=C/CN2CCCCC2)N(C1=O)S(=O)(=O)C.Cl
• Canonical SMILES: CC([C@H]1[C@@H]2N(CCC2N(C1=O)S(=O)(=O)C)C(=O)/C=C/CN1CCCCC1)C.Cl
• InChI: InChI=1S/C19H31N3O4S.ClH/c1-14(2)17-18-15(22(19(17)24)27(3,25)26)9-13-21(18)16(23)8-7-12-20-10-5-4-6-11-20;/h7-8,14-15,17-18H,4-6,9-13H2,1-3H3;1H/t15?,17-,18+;/m0./s1
• InChIKey: UFCZUKYPBPXODT-MXWDRHHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS)-1-methanesulfonyl-4-[4-(piperidin-1-yl)but-2-enoyl]-3-(propan-2-yl)-octahydropyrrolo[3,2-b]pyrrol-2-one hydrochloride
• IUPAC Traditional name: (3S,3aS)-3-isopropyl-1-methanesulfonyl-4-[4-(piperidin-1-yl)but-2-enoyl]-tetrahydro-3H-pyrrolo[3,2-b]pyrrol-2-one hydrochloride
• Synonyms: (3S,3aS,6aR)-3-Isopropyl-1-(methanesulfonyl)-4-[4-(1-piperidinyl)-2(E)-butenoyl]perhydropyrrolo[3,2b]pyrrol-2(1H)-one hydrochloride; GW311616A

Database IDs

• CAS Number: 197090-44-1
• MDL Number: MFCD06411566
• PubChem SID: 162248408
• PubChem CID: 71311827

CALCULATED PROPERTIES

• Acid pKa: 19.71483
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -2.3036096
• LogD (pH = 7.4): -0.55084836
• Log P: 0.56472796
• Molar Refractivity: 104.8857 cm^3
• Polarizability: 41.456802 Å^3
• Polar Surface Area: 78.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble24 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C19H32ClN3O4S

DETAILS

Sigma Aldrich - G8419

Biochem/physiol Actions
Potent, intracellular human neutrophil elastase (HNE, α-1-proteinase) inhibitor.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline