(4S,7R)-10-bromo-N-[(1S,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]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

• ChemBase ID: 162677
• Molecular Formular: C32H40BrN5O5
• Molecular Mass: 654.5945
• Monoisotopic Mass: 653.22128141
• SMILES: c1cc2[nH]c(c3C[C@@H]4C(=C[C@@H](CN4C)C(=O)N[C@]4(C(=O)N5[C@@](O4)([C@H]4N(C(=O)[C@@H]5CC(C)C)CCC4)O)C(C)C)c(c1)c23)Br
• Canonical SMILES: CC(C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@@](O2)(NC(=O)[C@@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c([nH]3)Br)C(C)C)O)C
• InChI: InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23+,24-,25-,31+,32-/m0/s1
• InChIKey: OZVBMTJYIDMWIL-SHUSXKRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7R)-10-bromo-N-[(1S,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]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• IUPAC Traditional name: (4S,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• Synonyms: (5’α,8α)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione; 2-Bromo-α-ergocryptinine; 2-Bromo-α-ergokryptinin; 8-Epibromocriptine; 8-Isobromocriptine; Isobromocriptine; (8S)-2-Bromo-α-Ergocryptine

Database IDs

• CAS Number: 65700-36-9
• PubChem SID: 162256812
• PubChem CID: 13187203

CALCULATED PROPERTIES

• Acid pKa: 9.677615
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.6492515
• LogD (pH = 7.4): 3.8034801
• Log P: 3.8871677
• Molar Refractivity: 165.5124 cm^3
• Polarizability: 65.108116 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B682605

The (8S)-epimer of 2-Bromo-α-Ergocryptine (B682600), as impurity. Dopamine receptor agonist; derivative of the ergotoxin group of ergot alkaloids. Prolactin inhibitor; antiparkinsonian.

REFERENCES

• Giron-Forest,D.A., et al.: Anal. Profiles Drug Subs., 8, 47 (1979)
• Camerman, N., et al.: Mol. Pharmacol., 19, 517 (1979)
• Ho, K.Y., et al.: Drugs, 36, 67 (1979)