(2Z)-but-2-enedioic acid; 1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}(2H5)propan-2-ol

• ChemBase ID: 178656
• Molecular Formular: C17H28N4O7S
• Molecular Mass: 432.49182
• Monoisotopic Mass: 432.16787026
• SMILES: C(=C\C(=O)O)\C(=O)O.c1(c(nsn1)OCC(CNC(C)(C)C)O)N1CCOCC1
• Canonical SMILES: OC(COc1nsnc1N1CCOCC1)CNC(C)(C)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C13H24N4O3S.C4H4O4/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17;5-3(6)1-2-4(7)8/h10,14,18H,4-9H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: WLRMANUAADYWEA-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}(^2H₅)propan-2-ol
• IUPAC Traditional name: 1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}(^2H₅)propan-2-ol; maleic acid
• Synonyms: 1-[(1,1-Dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-2-propanol (2Z)-2-Butenedioate-d5; (+/-)-Timolol maleate-d5; NSC 312896-d5; rac Timolol-d5 Maleate

Database IDs

• PubChem SID: 164234566
• PubChem CID: 46783095

CALCULATED PROPERTIES

• Acid pKa: 14.084203
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.86655
• LogD (pH = 7.4): -0.97262925
• Log P: 1.335706
• Molar Refractivity: 83.92 cm^3
• Polarizability: 31.508137 Å^3
• Polar Surface Area: 79.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 210-212°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T443702

Antihypertensive; antiarrhythmic (class II); antianginal; antiglaucoma agent.

REFERENCES

• Wasson, et al.: J. Med. Chem., 15, 651 (1972)
• Franciosa, et al.: Clin. Pharmacol. Ther., 13, 138 (1972)
• Heel, R.C., et al.: Drugs, 17, 38 (1972)
• Rofman, B.A., et al.: Hypertension, 2, 643 (1972)
• Mazzo, D.J., et al.: Anal. Profiles Drug Subs., 16, 641