(2Z)-but-2-enedioic acid; 3-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-1-pentylguanidine

• ChemBase ID: 178113
• Molecular Formular: C20H27N5O5
• Molecular Mass: 417.45888
• Monoisotopic Mass: 417.20121899
• SMILES: c1c(cc2c(c1)[nH]cc2/C=N/NC(=N)NCCCCC)OC.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CCCCCNC(=N)N/N=C/c1c[nH]c2c1cc(OC)cc2
• InChI: InChI=1S/C16H23N5O.C4H4O4/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15;5-3(6)1-2-4(7)8/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21);1-2H,(H,5,6)(H,7,8)/b20-11+;2-1-
• InChIKey: CPDDZSSEAVLMRY-FEQFWAPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 3-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-1-pentylguanidine
• IUPAC Traditional name: maleic acid; tegaserod
• Synonyms: 2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide (2Z)-2-Butenedioate; HTF 919; SDZ-HTF 919; Tegaserod Hydrogen Maleate; Tegibs 6; Zelmac; Zelnorm; Tegaserod Maleate

Database IDs

• CAS Number: 189188-57-6
• PubChem SID: 164234023
• PubChem CID: 6918369

CALCULATED PROPERTIES

• Acid pKa: 15.243261
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.63871306
• LogD (pH = 7.4): 1.8410585
• Log P: 2.9544108
• Molar Refractivity: 110.2496 cm^3
• Polarizability: 34.663303 Å^3
• Polar Surface Area: 85.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 182-184°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T014500

Tegaserod is a gastroproeinetic used in the treatment of irritable bowel syndrome. A selective serotonin 5HT4-receptor partial agonist.

REFERENCES

• Appel, S., et al.: Clin. Pharmacol. Ther., 62, 546 (1997)