2-methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 172633
• Molecular Formular: C36H48O2
• Molecular Mass: 512.76512
• Monoisotopic Mass: 512.36543078
• SMILES: c1ccc2c(c1)C(=O)C(=C(C2=O)C)C/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)\C
• Canonical SMILES: C/C(=C\CC/C(=C/CC1=C(C)C(=O)c2c(C1=O)cccc2)/C)/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C
• InChI: InChI=1S/C36H48O2/c1-26(2)14-10-15-27(3)16-11-17-28(4)18-12-19-29(5)20-13-21-30(6)24-25-32-31(7)35(37)33-22-8-9-23-34(33)36(32)38/h8-9,14,16,18,20,22-24H,10-13,15,17,19,21,25H2,1-7H3/b27-16+,28-18+,29-20+,30-24+
• InChIKey: HYPYXGZDOYTYDR-HAJWAVTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: 2-methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]naphthalene-1,4-dione
• Synonyms: 2-Methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaen-1-yl]-1,4-naphthalenedione; 2-Methyl-3-farnesylgeranyl-1,4-naphthoquinone; Menaquinone; Vitamin K2(25); Vitamin MK 5; Menaquinone 5

Database IDs

• CAS Number: 1182-68-9
• PubChem SID: 164228543
• PubChem CID: 14009404

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 10.139421
• LogD (pH = 7.4): 10.139421
• Log P: 10.139421
• Molar Refractivity: 169.3094 cm^3
• Polarizability: 63.639606 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false
• H Acceptors: 2

DETAILS

Toronto Research Chemicals - M218585

Menaquinones are isoprenoid quinones of the naphthalene series and belongs to the K2 Vitamin homologs. Menaquinones were originally discovered as the anti-hemorrhagic factor and now encompasses a variety of physiological processes.

REFERENCES

• Hugenholtz, P., et al.: J. Bacteriol., 180, 4765 (1998)
• Ginet, N., et al.: Biochemistry, 40, 1812 (1998)
• Cape, J., et al.: J. Biol. Chem., 280, 34654 (1998)