(7R)-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: 168155
• Molecular Formular: C32H41N5O5
• Molecular Mass: 575.69844
• Monoisotopic Mass: 575.31076944
• SMILES: c1cc2[nH]cc3C[C@@H]4C(=CC(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
• Canonical SMILES: CC(C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@@](O2)(NC(=O)C1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C(C)C)O)C
• InChI: InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20?,24-,25+,26+,31-,32+/m1/s1
• InChIKey: YDOTUXAWKBPQJW-BWWHSAEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R)-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: (7R)-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: Ergokryptinine; Isoergokryptine; α-Ergocryptinine; α-Ergokryptinine; (5'α,8α)-12'-Hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-ergotaman-3',6',18-trione; α-Ergocryptinine

Database IDs

• CAS Number: 511-10-4
• PubChem SID: 162262287
• PubChem CID: 12309771

CALCULATED PROPERTIES

• Acid pKa: 9.695993
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.1555935
• LogD (pH = 7.4): 2.8807073
• Log P: 3.3118112
• Molar Refractivity: 158.1076 cm^3
• Polarizability: 62.306118 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E597520

Ergot alkaloids.

REFERENCES

• Kantorova, M. et al.: J. Nat. Prod. 65, 1039 (2002)
• Rotter, R. et al.: Can. J. Anim. Sci. 65, 953 (1985)