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

• ChemBase ID: 127285
• Molecular Formular: C32H41N5O5
• Molecular Mass: 575.69844
• Monoisotopic Mass: 575.31076944
• SMILES: O=C1N2CCC[C@H]2[C@]2(O)O[C@](C(=O)N2[C@H]1CC(C)C)(NC(=O)[C@@H]1C=C2c3cccc4c3c(c[nH]4)C[C@H]2N(C)C1)C(C)C
• 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-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: α-ergocryptine
• Synonyms: (5'α)-12'-Hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione; Ergocryptine; Ergokryptine; NSC 169479; NSC 407319; α-Ergocryptine; α-Ergokryptine; α-Ergocryptine; Ergocryptine; 12′-Hydroxy-2′-(1-methylethyl)-5′-α-(2-methylpropyl)ergotaman-3′,6′,18-trione; α-Ergocryptine; Ergocryptin

Database IDs

• CAS Number: 511-09-1
• EC Number: 208-121-2
• PubChem SID: 162221606; 24894618
• PubChem CID: 134551
• Chemspider ID: 118591
• Wikipedia Title: Ergocryptine

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: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.3 mg/mL; Chloroform; ethanol: soluble3.2 mg/mL; H2O: insoluble; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >148°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: KE1400000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 62
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C32H41N5O5

DETAILS

Sigma Aldrich - E5625

Biochem/physiol Actions
Ergot alkaloid

Toronto Research Chemicals - E597500

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)