(2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecane-4-carboxylic acid

• ChemBase ID: 175770
• Molecular Formular: C17H26N2O6
• Molecular Mass: 354.39814
• Monoisotopic Mass: 354.17908656
• SMILES: [C@]12(N([C@H](C(=O)N3C1CCC3)CC(C)C)C(=O)[C@](O2)(C(C)C)C(=O)O)O
• Canonical SMILES: CC(C[C@H]1C(=O)N2CCCC2[C@]2(N1C(=O)[C@](O2)(C(C)C)C(=O)O)O)C
• InChI: InChI=1S/C17H26N2O6/c1-9(2)8-11-13(20)18-7-5-6-12(18)17(24)19(11)14(21)16(25-17,10(3)4)15(22)23/h9-12,24H,5-8H2,1-4H3,(H,22,23)/t11-,12?,16+,17-/m0/s1
• InChIKey: BRHAPIBGUBQOTE-VDXHGNKCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecane-4-carboxylic acid
• IUPAC Traditional name: (2S,4R,7S)-2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecane-4-carboxylic acid
• Synonyms: [2R-(2α,5α,10aβ,10bα)]-Octahydro-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine-2-carboxylic acid; (2R,5S,10aS,10bS)-Octahydro-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine-2-carboxylic Acid

Database IDs

• CAS Number: 24177-07-9
• PubChem SID: 164231680
• PubChem CID: 71751276

CALCULATED PROPERTIES

• Acid pKa: 3.4693763
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.45569646
• LogD (pH = 7.4): -1.8209243
• Log P: 1.5654249
• Molar Refractivity: 86.63 cm^3
• Polarizability: 34.262672 Å^3
• Polar Surface Area: 107.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - O236475

Used in the synthesis of Ergot alkaloids.