(3S,4R)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

• ChemBase ID: 155537
• Molecular Formular: C16H18N2O3
• Molecular Mass: 286.32572
• Monoisotopic Mass: 286.13174245
• SMILES: CC1([C@H]([C@@H](c2cc(ccc2O1)C#N)N1CCCC1=O)O)C
• Canonical SMILES: N#Cc1ccc2c(c1)[C@@H](N1CCCC1=O)[C@@H](C(O2)(C)C)O
• InChI: InChI=1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m1/s1
• InChIKey: TVZCRIROJQEVOT-CABCVRRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile
• IUPAC Traditional name: (-)-cromakalim
• Synonyms: (±)-trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol; Cromakalim

Database IDs

• CAS Number: 94470-67-4
• MDL Number: MFCD00133201
• PubChem SID: 24891962; 162249675
• PubChem CID: 93504

CALCULATED PROPERTIES

• Acid pKa: 13.255401
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0220234
• LogD (pH = 7.4): 1.0220231
• Log P: 1.0220237
• Molar Refractivity: 76.6727 cm^3
• Polarizability: 29.792604 Å^3
• Polar Surface Area: 73.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Pharmacology Properties

• Gene Information: rat ... Kcna1(24520), Kcnj1(24521), Kcnj5(29713), Kcnj8(25472)

Product Information

• Empirical Formula (Hill Notation): C16H18N2O3

DETAILS

Sigma Aldrich - C1055

Frequently Asked Questions
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Biochem/physiol Actions
Causes vasodilation by activation of potassium channels.