(4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; but-2-enedioic acid

• ChemBase ID: 168156
• Molecular Formular: C23H27N3O6
• Molecular Mass: 441.47698
• Monoisotopic Mass: 441.1899856
• SMILES: C12=C[C@H](CN([C@@H]1Cc1c3c2cccc3[nH]c1)C)C(=O)N[C@H](CO)C.C(=CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C=CC(=O)O.OC[C@@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C
• InChI: InChI=1S/C19H23N3O2.C4H4O4/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13;5-3(6)1-2-4(7)8/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24);1-2H,(H,5,6)(H,7,8)/t11-,13+,17+;/m0./s1
• InChIKey: YREISLCRUMOYAY-VSDOXBCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(2S)-1-hydroxypropan-2-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; but-2-enedioic acid
• IUPAC Traditional name: butenedioic acid; ergonovine
• Synonyms: (8β)-9,10-Didehydro-N-[(1S)-2-hydroxy-1-methylethyl]-6-methylergoline-8-carboxamide (2Z)-2-Butenedioate; 9,10-Didehydro-N-((S)-2-hydroxy-1-methylethyl)-6-methylergoline-8β-carboxamide Maleate; N-[(S)-2-Hydroxy-1-methylethyl]lysergamide Maleate; D-Lysergic Acid-L-propanolamide Maleate; Cornocentin; D-Ergonovine Maleate; Ergobasine Maleate; Ergomet; Ergometrin Maleate; Ergometrine Acid Maleate; Ergometrine hydrogen maleate; Ergometrine Maleate; Ergotrate; Ermetrin; Ermetrine; NSC 93752; Oxytocic; Ergonovine Maleate Salt

Database IDs

• CAS Number: 129-51-1
• PubChem SID: 162262288
• PubChem CID: 443883

CALCULATED PROPERTIES

• Acid pKa: 14.998553
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.3230772
• LogD (pH = 7.4): 0.43092284
• Log P: 1.070696
• Molar Refractivity: 95.0519 cm^3
• Polarizability: 37.447586 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E597800

Ergonovine is an oxytocic, stimulates contraction of uterine muscle; partial agonist at serotonergic and dopaminergic receptors in CNS; selective, potent antagonist at smooth muscle serotonergic receptors.

REFERENCES

• Meisheri, K., et al.: Eur. J. Pharmacol., 60, 1 (1979)
• de Groot, A., et al.: Drugs, 56, 523 (1979)
• Carvalho, J., et al.: Obstet. Gynecol., 104, 1005 (1979)