(2E)-but-2-enedioic acid; {3-[2-(dimethylamino)ethyl]-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-1-yl}methanol

• ChemBase ID: 170923
• Molecular Formular: C20H25N5O5
• Molecular Mass: 415.443
• Monoisotopic Mass: 415.18556893
• SMILES: c1cc(cc2c1n(cc2CCN(C)C)CO)Cn1cncn1.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.OCn1cc(c2c1ccc(c2)Cn1cncn1)CCN(C)C
• InChI: InChI=1S/C16H21N5O.C4H4O4/c1-19(2)6-5-14-9-20(12-22)16-4-3-13(7-15(14)16)8-21-11-17-10-18-21;5-3(6)1-2-4(7)8/h3-4,7,9-11,22H,5-6,8,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: IVPBRIIBZGSYKW-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; {3-[2-(dimethylamino)ethyl]-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-1-yl}methanol
• IUPAC Traditional name: fumaric acid; {3-[2-(dimethylamino)ethyl]-5-(1,2,4-triazol-1-ylmethyl)indol-1-yl}methanol
• Synonyms: N,N-Dimethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1-hydroxymethyl-indole-3-ethanamine trans-Butenedioic Acid; Rizatriptan Impurity A; N-Hydroxymethyl Rizatriptan Fumarate

Database IDs

• PubChem SID: 164226833
• PubChem CID: 71749186

CALCULATED PROPERTIES

• Acid pKa: 13.9426565
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.9748724
• LogD (pH = 7.4): -0.692835
• Log P: 1.4115543
• Molar Refractivity: 99.1308 cm^3
• Polarizability: 34.085026 Å^3
• Polar Surface Area: 59.11 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948410

An impurity of the antimigraine drug Rizatriptan (R545000).