(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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: 127284
• Molecular Formular: C35H39N5O5
• Molecular Mass: 609.71466
• Monoisotopic Mass: 609.29511937
• SMILES: O=C1N2CCC[C@H]2[C@]2(O)O[C@](C(=O)N2[C@H]1Cc1ccccc1)(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](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O)C(C)C
• InChI: InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1
• InChIKey: HEFIYUQVAZFDEE-MKTPKCENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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(15),2,9,12(16),13-pentaene-4-carboxamide
• IUPAC Traditional name: ergocristine
• Synonyms: Ergocristine; 12′-Hydroxy-2′-(1-methylethyl)-5′-(phenylmethyl)ergotaman-3′,6′,18′-trione; Ergocristine; (5'α)-12'-Hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)ergotaman-3',6',18-trione; Ergocrystine; NSC 93743

Database IDs

• CAS Number: 511-08-0
• EC Number: 208-120-7
• MDL Number: MFCD00215848
• PubChem SID: 162221605
• PubChem CID: 31116
• CHEMBL: 446315
• Chemspider ID: 28873
• Wikipedia Title: Ergocristine

CALCULATED PROPERTIES

• Acid pKa: 9.695265
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.55781
• LogD (pH = 7.4): 3.2829201
• Log P: 3.7138987
• Molar Refractivity: 169.053 cm^3
• Polarizability: 66.369675 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: soluble0.44 mg/mL; ethanol: soluble20 mg/mL; H2O: insoluble
• Melting Point: 155-157 °C(lit.)

Safety Information

• RTECS: KE1180000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25
• Safety Statements: 22-36/37/39-45
• RID/ADR: UN 1544 6.1/PG 3

DETAILS

Sigma Aldrich - E140

Biochem/physiol Actions
Ergot alkaloid

Toronto Research Chemicals - E597450

A derivative of lysergic acid and a natural ergot alkaloid which is a member of the ergotoxine group. Its intraocular pressure lowering effect makes it potential candidate for future applications in ocular pharmacology.

REFERENCES

• Puras, G. et al.: J. Ocul. Pharmacol., 18, 41 (2002)
• Mainka, S. et al.: Arch. Anim. Nutrit., 59, 377 (2002)
• Puras, G.: Alkaloids, 37 (2002)