LIPID MAPS

Structure Database (LMSD)

Common Name

Menaquinone-9

Systematic Name

2-methyl-3-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl)naphthalene-1,4-dione

Synonyms

MK-9

LM ID

LMPR02010041

Formula

C₅₆H₈₀O₂

Exact Mass

Calculate m/z

784.61583

Status

Curated

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Classification

Biological Context

Menaquinone 9 (MK-9) is a vitamin K2 analog that has been found in various bacteria, including E. coli.^1,2 MK-9 is UV-sensitive and binds to soluble nitrate reductase, a component of the bacterial electron transport chain.¹ In vivo, MK-9 increases plasma prothrombin concentration in vitamin K-deficient rats.²

This information has been provided by Cayman Chemical

References

1. Brito, F., DeMoss, J.A., and Dubourdieu, M. Isolation and identification of menaquinone-9 from purified nitrate reductase of Escherichia coli. J. Bacteriol. 177(13), 3728-3735 (1995).

2. Craciun, A.M., Groenen-van Dooren, M.M., Thijssen, H.H., et al. Induction of prothrombin synthesis by K-vitamins compared in vitamin K-deficient and in brodifacoum-treated rats. Biochim. Biophys. Acta 1380(1), 75-81 (1998).

String Representations

InChiKey (Click to copy)

WCRXHNIUHQUASO-UVZVDVBNSA-N

InChi (Click to copy)

InChI=1S/C56H80O2/c1-42(2)22-14-23-43(3)24-15-25-44(4)26-16-27-45(5)28-17-29-46(6)30-18-31-47(7)32-19-33-48(8)34-20-35-49(9)36-21-37-50(10)40-41-52-51(11)55(57)53-38-12-13-39-54(53)56(52)58/h12-13,22,24,26,28,30,32,34,36,38-40H,14-21,23,25,27,29,31,33,35,37,41H2,1-11H3/b43-24+,44-26+,45-28+,46-30+,47-32+,48-34+,49-36+,50-40+

SMILES (Click to copy)

C1(C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C)C(=O)C2=C(C=CC=C2)C(=O)C=1C