(2Z)-but-2-enedioic acid; (4R,7R)-N-[(2S)-1-hydroxy(3,3,4,4,4-2H5)butan-2-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: 173681
• Molecular Formular: C24H29N3O6
• Molecular Mass: 455.50356
• Monoisotopic Mass: 455.20563566
• SMILES: C(=C\C(=O)O)\C(=O)O.c1cc2[nH]cc3C[C@@H]4C(=C[C@H](CN4C)C(=O)N[C@@H](CC)CO)c(c1)c23
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CO
• InChI: InChI=1S/C20H25N3O2.C4H4O4/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13;5-3(6)1-2-4(7)8/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-,14+,18-;/m1./s1
• InChIKey: NOFOWWRHEPHDCY-DAUURJMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; (4R,7R)-N-[(2S)-1-hydroxy(3,3,4,4,4-^2H₅)butan-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
• IUPAC Traditional name: (4R,7R)-N-[(2S)-1-hydroxy(3,3,4,4,4-^2H₅)butan-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; maleic acid
• Synonyms: (8β)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl-d5]-6-methyl-ergoline-8-carbox-amide Maleate; N-[α-(Hydroxymethyl)propyl]-D-lysergamide-d5 Maleate; Basofortina-d5; Erezin-d5; Metenarin-d5; Methergin-d5; Methergine-d5; Methyl Ergonovine-d5 Maleate Salt

Database IDs

• PubChem SID: 164229591
• PubChem CID: 46782242

CALCULATED PROPERTIES

• Acid pKa: 14.997192
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.80055475
• LogD (pH = 7.4): 0.95344526
• Log P: 1.5932183
• Molar Refractivity: 99.5759 cm^3
• Polarizability: 39.292522 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Grey Solid
• Melting Point: 185-187°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M304602

A labelled metabolite of Methysergide. Semisynthetic ergot alkaloid. Oxytocic.

REFERENCES

• Mueller, L., et al.: Headache, 37, 437 (1997)
• de Groot, A.N., et al.: Drugs, 56, 523 (1997)