(2E)-but-2-enedioic acid; bis(4-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1H-indole-2-carbonitrile)

• ChemBase ID: 131791
• Molecular Formular: C36H46N6O8
• Molecular Mass: 690.78584
• Monoisotopic Mass: 690.33771246
• SMILES: CC(C)(C)NC[C@@H](COc1cccc2c1cc([nH]2)C#N)O.CC(C)(C)NC[C@@H](COc1cccc2c1cc([nH]2)C#N)O.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.N#Cc1[nH]c2c(c1)c(OC[C@H](CNC(C)(C)C)O)ccc2.N#Cc1[nH]c2c(c1)c(OC[C@H](CNC(C)(C)C)O)ccc2
• InChI: InChI=1S/2C16H21N3O2.C4H4O4/c2*1-16(2,3)18-9-12(20)10-21-15-6-4-5-14-13(15)7-11(8-17)19-14;5-3(6)1-2-4(7)8/h2*4-7,12,18-20H,9-10H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*12-;/m00./s1
• InChIKey: ZSBITJKBOWVCCI-SODPCTSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; bis(4-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1H-indole-2-carbonitrile)
• IUPAC Traditional name: bis(4-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1H-indole-2-carbonitrile); fumaric acid
• Synonyms: 4-[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-1H-indole-2-carbonitrile hemifumarate salt; S(-)-Cyanopindolol hemifumarate salt

Database IDs

• CAS Number: 874882-72-1
• PubChem SID: 24892321; 162226068
• PubChem CID: 71308473

CALCULATED PROPERTIES

• Acid pKa: 12.722954
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.4526042
• LogD (pH = 7.4): -0.55872244
• Log P: 1.7496551
• Molar Refractivity: 81.6993 cm^3
• Polarizability: 33.093365 Å^3
• Polar Surface Area: 81.07 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white solid
• Optical Rotation: [α]20/D -13.0°, c = 0.215 in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - C238

Biochem/physiol Actions
5-HT1A/1B serotonin receptor antagonist; β3-adrenoceptor antagonist.