{[(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl](phenyl)phosphoroso}benzene

• ChemBase ID: 153968
• Molecular Formular: C22H29OP
• Molecular Mass: 340.438821
• Monoisotopic Mass: 340.19560218
• SMILES: C[C@@H]1CC[C@H]([C@H](C1)P(=O)(c1ccccc1)c1ccccc1)C(C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@H](C1)P(=O)(c1ccccc1)c1ccccc1)C(C)C
• InChI: InChI=1S/C22H29OP/c1-17(2)21-15-14-18(3)16-22(21)24(23,19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m1/s1
• InChIKey: BPCNGVCAHAIZEE-COPCDDAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl](phenyl)phosphoroso}benzene
• IUPAC Traditional name: [(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl(phenyl)phosphoroso]benzene
• Synonyms: (+)-Neomenthyl diphenylphosphine oxide; (1S,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]diphenyl-phosphine oxide; DPO-1

Database IDs

• CAS Number: 43077-30-1
• MDL Number: MFCD09038567
• PubChem SID: 162248107
• PubChem CID: 21678144

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.1539
• LogD (pH = 7.4): 6.1539
• Log P: 6.1539
• Molar Refractivity: 102.5 cm^3
• Polarizability: 41.080776 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL at ~60 °C, clear
• Apperance: white needles

Safety Information

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

Product Information

• Purity: >97% (NMR)
• Empirical Formula (Hill Notation): C22H29OP

DETAILS

Sigma Aldrich - D7443

Biochem/physiol Actions
DPO-1 is an inhibitor of human Kv1.5 potassium channel; representative blocker of a novel pharmacophore. The Kv1.5 potassium channel, which underlies the ultrarapid delayed rectifier current, IKur, is reported to be enriched in human atrium versus ventricle, and has been proposed as a target for novel atrial antiarrhythmic therapy. The administration of the IKur blocker (2-isopropyl-5-methyl-cyclohexyl) diphenylphosphine oxide (DPO-1) increases myocardial refractoriness in both atrium and ventricle of rat, but produces an atrial-selective increase in refractoriness in primates; appears to be 15-fold more selective for Kv1.5 vs Kv3.1 channels expressed in Xenopus oocytes. IC50 = 0.16-0.76 μM at 0.1 Hz pulsing frequency; Kd = 0.6 μM.