(2R)-2,8-dimethyl-5-(morpholin-4-ylmethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

• ChemBase ID: 174823
• Molecular Formular: C32H55NO3
• Molecular Mass: 501.784
• Monoisotopic Mass: 501.41819463
• SMILES: c1(cc(c(c2c1O[C@@](CC2)(CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)C)CN1CCOCC1)O)C
• Canonical SMILES: C[C@H](CCC[C@@H](CCCC(C)C)C)CCC[C@]1(C)CCc2c(O1)c(C)cc(c2CN1CCOCC1)O
• InChI: InChI=1S/C32H55NO3/c1-24(2)10-7-11-25(3)12-8-13-26(4)14-9-16-32(6)17-15-28-29(23-33-18-20-35-21-19-33)30(34)22-27(5)31(28)36-32/h22,24-26,34H,7-21,23H2,1-6H3/t25-,26-,32-/m1/s1
• InChIKey: NHGONPYIGRKKFZ-ZAOJZYTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2,8-dimethyl-5-(morpholin-4-ylmethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• IUPAC Traditional name: (2R)-2,8-dimethyl-5-(morpholin-4-ylmethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-1-benzopyran-6-ol
• Synonyms: 2-(4-Morpholinylimino)acetonitrile; (Morpholinoimino)acetonitrile; SIN 1C; Molsidomine Impurity C; (4-Morpholinylimino)acetonitrile

Database IDs

• CAS Number: 26179-71-5
• PubChem SID: 164230733
• PubChem CID: 16116401

CALCULATED PROPERTIES

• Acid pKa: 9.35882
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 7.4433193
• LogD (pH = 7.4): 8.959442
• Log P: 9.203771
• Molar Refractivity: 152.9089 cm^3
• Polarizability: 60.122566 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M723780

(4-Morpholinylimino)acetonitrile is an impurity of Molsidomine (M488000). (4-Morpholinylimino)acetonitrile is also a metabolite of 3-Morpholino Sydnonimine (M725000). Molsidomine Impurity C.

REFERENCES

• Kankaanranta, H., et al.: Biochem. Pharmacol., 50, 197 (1987)
• Feelisch, M., et al.: Eur. J. Pharmacol., 142, 465 (1987)
• Feelisch, M., et al.: J. Cardiovasc. Pharmacol., 17, S25 (1987)
• Knowles, R., et al.: Biochem. J., 298, 249 (1987)