(4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-bis(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: 127283
• Molecular Formular: C31H39N5O5
• Molecular Mass: 561.67186
• Monoisotopic Mass: 561.29511937
• SMILES: O=C1N2CCC[C@H]2[C@]2(O)O[C@](C(=O)N2[C@H]1C(C)C)(NC(=O)[C@@H]1C=C2c3cccc4c3c(c[nH]4)C[C@H]2N(C)C1)C(C)C
• Canonical SMILES: O=C([C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@@]1(O[C@@]2(N(C1=O)[C@@H](C(C)C)C(=O)N1[C@H]2CCC1)O)C(C)C
• InChI: InChI=1S/C31H39N5O5/c1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19/h6,8-9,12,14,16-17,19,23-24,26,32,40H,7,10-11,13,15H2,1-5H3,(H,33,37)/t19-,23-,24+,26+,30-,31+/m1/s1
• InChIKey: UJYGDMFEEDNVBF-OGGGUQDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-bis(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; (4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-bis(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(15),2,9,12(16),13-pentaene-4-carboxamide
• IUPAC Traditional name: ergocornine
• Synonyms: Ergocornine; 12′-Hydroxy-2′,5′-α-bis(1-methyl-ethyl)ergotaman-3′,6′,18-trion; Ergocornine; Ergocornin

Database IDs

• CAS Number: 564-36-3
• EC Number: 209-272-7
• MDL Number: MFCD00274574
• PubChem SID: 162221604; 24894401
• PubChem CID: 73453
• Chemspider ID: 66155
• Wikipedia Title: Ergocornine

CALCULATED PROPERTIES

• Acid pKa: 9.69552
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.7889788
• LogD (pH = 7.4): 2.5140896
• Log P: 2.9451122
• Molar Refractivity: 153.4296 cm^3
• Polarizability: 60.46683 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.4 mg/mL; DMSO: soluble6.5 mg/mL; ethanol: soluble1.02 mg/mL; H2O: insoluble
• Apperance: white solid
• Optical Rotation: [α]/D -105.6°, c = 0.85 in pyridine(lit.)

Safety Information

• RTECS: KE7630000
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1544 6.1/PG 3

Product Information

• Purity: >95%

DETAILS

Sigma Aldrich - E131

Biochem/physiol Actions
Dopamine receptor agonist; ergot alkaloid.