Structure Database (LMSD)

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
Calculate m/z
450.34978
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Quinones and hydroquinones [PR02]
Vitamin K [PR0203]

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

Other Databases

Wikipedia
phylloquinone
KEGG ID
C02059
HMDB ID
HMDB0004198
CHEBI ID
18067
PubChem CID
5284607
SwissLipids ID
SLM:000390033
Cayman ID
21051
PDB ID
PQN

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 2
Aromatic Rings 1
Rotatable Bonds 14
Van der Waals Molecular Volume 508.34
Topological Polar Surface Area 34.14
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 9.16
Molar Refractivity 140.90

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Updated at
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