(4R,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-(2H3)methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

• ChemBase ID: 168154
• Molecular Formular: C32H41N5O5
• Molecular Mass: 575.69844
• Monoisotopic Mass: 575.31076944
• SMILES: c1cc2[nH]cc3C[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
• 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)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-NSLWYYNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,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-(^2H₃)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: (4R,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-(^2H₃)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)-12'-Hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione-d3; Ergocryptine-d3; Ergokryptine-d3; NSC 169479-d3; NSC 407319-d3; α-Ergocryptine-d3; α-Ergokryptine-d3; α-Ergocryptine-d3

Database IDs

• PubChem SID: 162262286
• PubChem CID: 71316400

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: 62.30612 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E597502

Labelled α-Ergocryptine. α-Ergocryptine is an ergopeptine and one of the ergot alkaloids. An impurity of 2-Bromo-α-Ergocryptine Mesylate (B682600).

REFERENCES

• Young, J., et al.: J. Environ. Sci. Health, 16, 83 (1981)
• Sugrue, M., et al.: J. Med. Chem., 40, 2793 (1981)