{[3-(dimethyl-oxo-$l^{5}-azanyl)propyl](ethylcarbamoyl)amino}[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraen-4-yl]methanone

• ChemBase ID: 163522
• Molecular Formular: C26H37N5O3
• Molecular Mass: 467.60368
• Monoisotopic Mass: 467.28964007
• SMILES: C1[C@H]2[C@H](N(C[C@@H]1C(=O)N(CCC[N+]([O-])(C)C)C(=O)NCC)CC=C)Cc1c3c2cccc3[nH]c1
• Canonical SMILES: C=CCN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N(C(=O)NCC)CCC[N+](C)(C)[O-]
• InChI: InChI=1S/C26H37N5O3/c1-5-11-29-17-19(25(32)30(26(33)27-6-2)12-8-13-31(3,4)34)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)29/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
• InChIKey: MWKMKARCRODSLP-KJXAQDMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[3-(dimethyl-oxo-$l^{5}-azanyl)propyl](ethylcarbamoyl)amino}[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methanone
• IUPAC Traditional name: {[3-(dimethyl-oxo-$l^{5}-azanyl)propyl](ethylcarbamoyl)amino}[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methanone
• Synonyms: (3-{{[6aR,9R,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9yl]carbonyl}[ethylamino)carbonyl]amino}propyl)(dimethyl)ammoniumolate; Cabergoline N-Oxide

Database IDs

• PubChem SID: 162257657
• PubChem CID: 71314472

CALCULATED PROPERTIES

• Acid pKa: 14.946983
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0513412
• LogD (pH = 7.4): 0.7195425
• Log P: 1.4541411
• Molar Refractivity: 135.5478 cm^3
• Polarizability: 52.498222 Å^3
• Polar Surface Area: 95.32 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C050010

The N-oxide of Cabergoline (C050000), a dopamine D2-receptor agonist.

REFERENCES

• Brambilla, E., et al.: Eur. J. Med. Chem., 24, 421 (1989)
• Ferrari, C., et al.: J. Clin. Endocrinol. Metab., 68, 1201 (1989)
• Hutton, J.T., et al.: Neurology, 46, 1062 (1996)