(4R,7R)-9-hydroxy-N,6-dimethyl-10-oxo-N-propyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide

• ChemBase ID: 176014
• Molecular Formular: C20H25N3O3
• Molecular Mass: 355.4308
• Monoisotopic Mass: 355.18959168
• SMILES: c1cc2NC(=O)C3(C[C@@H]4C(=C[C@H](CN4C)C(=O)N(CCC)C)c(c1)c23)O
• Canonical SMILES: CN1C[C@@H](C=C2[C@H]1CC1(O)C(=O)Nc3c1c2ccc3)C(=O)N(CCC)C
• InChI: InChI=1S/C20H25N3O3/c1-4-8-22(2)18(24)12-9-14-13-6-5-7-15-17(13)20(26,19(25)21-15)10-16(14)23(3)11-12/h5-7,9,12,16,26H,4,8,10-11H2,1-3H3,(H,21,25)/t12-,16-,20?/m1/s1
• InChIKey: PSQLKUJBRLOLIQ-VRORWYBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-9-hydroxy-N,6-dimethyl-10-oxo-N-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide
• IUPAC Traditional name: (4R,7R)-9-hydroxy-N,6-dimethyl-10-oxo-N-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide
• Synonyms: (8β)-9,10-Didehydro-2,3-dihydro-3-hydroxy-N,6-dimethyl-2-oxo-N-propylergoline-8-carboxamide; 2-Oxo-3-hydroxy LAMPA; 2-Oxo-3-hydroxylysergic Acid Methyl Propyl Amide; 2-Oxo-3-hydroxy-N-methyl-N-propyl D-Lysergamide

Database IDs

• CAS Number: 249921-57-1
• PubChem SID: 164231924
• PubChem CID: 71751375

CALCULATED PROPERTIES

• Acid pKa: 11.563063
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.0698266
• LogD (pH = 7.4): -0.29866245
• Log P: 0.6566175
• Molar Refractivity: 101.8402 cm^3
• Polarizability: 38.300793 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O856880

A major metabolite of Lysergamide (L487990) used as internal standard.