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Structure Database (LMSD)

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Common Name

phylloquinone

Systematic Name

2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione

Synonyms

2-Methyl-3-phytyl-1,4-naphthoquinone
PHYLLOQUINONE
Phylloquinone
Phytonadione
Vitamin K1

LM ID

LMPR02030028

Formula

C₃₁H₄₆O₂

Exact Mass

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450.349781

Status

Curated

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Classification

Biological Context

Vitamin K1 is a fat-soluble, dietary nutrient that is essential for the synthesis of proteins important for blood-clotting, bone metabolism, and cell growth.¹ It is found in the photosynthetic tissues of green, leafy plants, where it acts as an electron acceptor forming part of the electron transport chain of Photosystem I.² Vitamin K1 also serves as a precursor to vitamin K2 and is reported to exhibit anticancer activity in various cell lines.^3,4

This information has been provided by Cayman Chemical

References

1. Beulens, J.W.J., Booth, S.L., van den Heuvel, E.G.H.M., et al. The role of menaquinones (vitamin K2) in human health. Br. J. Nutr. 110(8), 1357-1368 (2013).

2. Lamson, D.W., and Plaza, S.M. The anticancer effects of vitamin K. Altern. Med. Rev. 8(3), 303-318 (2003).

3. Plaza, S.M., and Lamson, D.W. Vitamin K2 in bone metabolism and osteoporosis. Altern. Med. Rev. 10(1), 24-35 (2005).

4. Santabarbara, S., Heathcote, P., and Evans, M.C.W. Modelling of the electron transfer reactions in Photosystem I by electron tunnelling theory: The phylloquinones bound to the PsaA and the PsaB reaction centre subunits of PS I are almost isoenergetic to the iron-sulfur cluster FX. Biochim. Biophys. Acta 1708(3), 283-310 (2005).

String Representations

InChiKey (Click to copy)

MBWXNTAXLNYFJB-NKFFZRIASA-N

InChi (Click to copy)

InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

SMILES (Click to copy)

C12C=CC=CC=1C(C(=C(C)C2=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=O