MiMeDB: Showing metabocard for Menatetrenone (MMDBc0000274)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:48:25 UTC

Update Date

2024-10-13 10:31:18 UTC

Metabolite ID

MMDBc0000274

Metabolite Identification

Common Name

Menatetrenone

Description

Menatetrenone, also known as MK-4, is a vitamin K compound used as a hemostatic agent, and also as adjunctive therapy for the pain of osteoporosis. Menatetrenone is one of the nine forms of vitamin K2 and is a short-chain menaquinone. MK-4 is produced via conversion of vitamin K1 in the body, in the testes, pancreas and arterial walls (Wikipedia ). Vitamin K2 is found in brassicas. Vitamin K2 is widely distributed in green leaves and vegetables. It is a fat-soluble dietary factor effective in controlling blood coagulation. All members of the vitamin K group of vitamins share a methylated naphthoquinone ring structure and vary in the aliphatic side chain attached at the 3-position. Phylloquinone (also known as vitamin K1) invariably contains in its side chain four isoprenoid residues, one of which is unsaturated. Human milk contains between 1 and 4 micrograms/litre of vitamin K1, while formula-derived milk can contain up to 100 micrograms/litre in supplemented formulas. Vitamin K2 concentrations in human milk appear to be much lower than those of vitamin K1. It is estimated that there is a 0.25 to 1.7 percent occurrence of vitamin K deficiency bleeding in the first week of the infant's life with a prevalence of 2-10 cases per 100,000 births. The biochemistry of how vitamin K is used to convert glutamic acid (Glu) to gamma-carboxyglutamic acid (Gla) has been elucidated over the past thirty years in academic laboratories throughout the world. Within the cell, vitamin K undergoes electron reduction to a reduced form of vitamin K (called vitamin K hydroquinone) by the enzyme vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes vitamin K hydroquinone to allow carboxylation of Glu to Gla; this enzyme is called the gamma-glutamyl carboxylase or the vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize vitamin K hydroquinone to vitamin K epoxide at the same time. The carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted into vitamin K by the vitamin K epoxide reductase. These two enzymes comprise the so-called vitamin K cycle. Vitamin K2 is one of the reasons why vitamin K is rarely deficient in a human diet (vitamin K is continually recycled in our cells). Vitamin K1 is also known as phylloquinone or phytomenadione (also called phytonadione). Vitamin K2 (menaquinone, menatetrenone) is normally produced by bacteria in the large intestine, and dietary deficiency is extremely rare unless the intestines are heavily damaged or are unable to absorb the molecule, or due to decreased production by normal flora, as seen in broad spectrum antibiotic use.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306301800182D          

 36 37  0  0  0  0            999 V2000
    9.2881   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18  7  1  0  0  0  0
 19  8  1  0  0  0  0
 21 20  1  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  2  0  0  0  0
 23  3  1  0  0  0  0
 23 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24  4  1  0  0  0  0
 24 15  1  0  0  0  0
 24 16  2  0  0  0  0
 25  5  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  2  0  0  0  0
 26  6  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  2  0  0  0  0
 28 18  2  0  0  0  0
 29 19  2  0  0  0  0
 29 28  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  2  0  0  0  0
 33 31  2  0  0  0  0
 34 14  1  0  0  0  0
 35 16  1  0  0  0  0
 36 20  1  0  0  0  0
M  END

HMDB0030017
     RDKit          3D
Menatetrenone
 73 74  0  0  0  0  0  0  0  0999 V2000
   -9.4523   -0.3062   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5857    0.1989   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6441   -0.4797    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    1.2349   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.8355    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4458    1.7756    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    0.3906   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -0.6532    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5662    0.0360   -1.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0980   -1.3140   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651   -1.3548   -2.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861   -0.8442   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203    0.5528   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -1.6692   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -1.2441    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966   -1.3560   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -0.9002    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -1.5816    2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795    0.1310    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    0.6428    1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.6211    0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8339   -0.0305    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -0.8004    2.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1985   -0.0311    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1425   -0.6584    1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400    0.6882   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8323    0.6722   -0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1163    1.3581   -1.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220    2.0535   -2.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    2.0619   -1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5213    1.3749   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802    1.3550   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2657    1.9866   -0.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9423   -0.3055   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3153    0.4133   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9094   -1.2847   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6550   -0.9720    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    0.1917    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9226   -1.3411    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7851    1.7169   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1109    2.9350    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9833    1.3928    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3925    2.3602   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634    2.2534    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5901   -1.5437    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149   -0.9780    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3849   -0.2585    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    0.7608   -2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7056   -1.6818   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.0523   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -2.3904   -2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.7788   -3.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    0.9959   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    1.1667   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.6638    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -2.6863   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -1.8758    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -0.2023    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -0.7418   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -2.4265   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6751   -0.8140    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -2.2914    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343   -2.1533    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767    0.6068   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4237    0.1528    2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.7241    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228   -0.0966    3.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5743   -1.1447    3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -1.6949    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6142    0.1149   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430    1.3221   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3649    2.5839   -3.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0406    2.6133   -2.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 29 30  1  0
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 31 32  1  0
 32 33  2  0
 32 21  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 13 53  1  0
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 14 56  1  0
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 16 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
M  END


  Mrv1652306301800182D          

 36 37  0  0  0  0            999 V2000
    9.2881   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18  7  1  0  0  0  0
 19  8  1  0  0  0  0
 21 20  1  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  2  0  0  0  0
 23  3  1  0  0  0  0
 23 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24  4  1  0  0  0  0
 24 15  1  0  0  0  0
 24 16  2  0  0  0  0
 25  5  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  2  0  0  0  0
 26  6  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  2  0  0  0  0
 28 18  2  0  0  0  0
 29 19  2  0  0  0  0
 29 28  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  2  0  0  0  0
 33 31  2  0  0  0  0
 34 14  1  0  0  0  0
 35 16  1  0  0  0  0
 36 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000274

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(=O)C2=CC=CC=C2C1=O)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O2/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/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

> <INCHI_KEY>
DKHGMERMDICWDU-GHDNBGIDSA-N

> <FORMULA>
C31H40O2

> <MOLECULAR_WEIGHT>
444.659

> <EXACT_MASS>
444.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.9249299778513

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
8.479707364333333

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.224343414413889

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
145.50680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
menatetrenone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030017
     RDKit          3D
Menatetrenone
 73 74  0  0  0  0  0  0  0  0999 V2000
   -9.4523   -0.3062   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5857    0.1989   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6441   -0.4797    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    1.2349   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.8355    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4458    1.7756    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    0.3906   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -0.6532    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5662    0.0360   -1.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0980   -1.3140   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651   -1.3548   -2.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861   -0.8442   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203    0.5528   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -1.6692   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -1.2441    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966   -1.3560   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -0.9002    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -1.5816    2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795    0.1310    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    0.6428    1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.6211    0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8339   -0.0305    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -0.8004    2.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1985   -0.0311    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1425   -0.6584    1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400    0.6882   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8323    0.6722   -0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1163    1.3581   -1.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220    2.0535   -2.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    2.0619   -1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5213    1.3749   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802    1.3550   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2657    1.9866   -0.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9423   -0.3055   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3153    0.4133   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9094   -1.2847   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6550   -0.9720    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    0.1917    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9226   -1.3411    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7851    1.7169   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1109    2.9350    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9833    1.3928    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3925    2.3602   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634    2.2534    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5901   -1.5437    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149   -0.9780    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3849   -0.2585    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    0.7608   -2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7056   -1.6818   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.0523   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -2.3904   -2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.7788   -3.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    0.9959   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    1.1667   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.6638    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -2.6863   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -1.8758    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -0.2023    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -0.7418   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -2.4265   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6751   -0.8140    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -2.2914    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343   -2.1533    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767    0.6068   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4237    0.1528    2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.7241    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228   -0.0966    3.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5743   -1.1447    3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -1.6949    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6142    0.1149   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430    1.3221   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3649    2.5839   -3.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0406    2.6133   -2.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 21  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 13 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
M  END

HEADER    PROTEIN                                 30-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-18         0                                  
HETATM    1  C   UNK     0      17.338  22.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.672  20.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  20.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  17.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338  20.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670  16.170   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      12.003  16.170   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       9.336  11.550   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.668   6.930   0.000  0.00  0.00           H+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6   26                                                            
CONECT    7    8   18                                                       
CONECT    8    7   19                                                       
CONECT    9   12   13                                                       
CONECT   10   14   15                                                       
CONECT   11   16   17                                                       
CONECT   12    9   22                                                       
CONECT   13    9   23                                                       
CONECT   14   10   23   34                                                  
CONECT   15   10   24                                                       
CONECT   16   11   24   35                                                  
CONECT   17   11   25                                                       
CONECT   18    7   28                                                       
CONECT   19    8   29                                                       
CONECT   20   21   25   36                                                  
CONECT   21   20   27                                                       
CONECT   22    1    2   12                                                  
CONECT   23    3   13   14                                                  
CONECT   24    4   15   16                                                  
CONECT   25    5   17   20                                                  
CONECT   26    6   27   30                                                  
CONECT   27   21   26   31                                                  
CONECT   28   18   29   30                                                  
CONECT   29   19   28   31                                                  
CONECT   30   26   28   32                                                  
CONECT   31   27   29   33                                                  
CONECT   32   30                                                            
CONECT   33   31                                                            
CONECT   34   14                                                            
CONECT   35   16                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

COMPND    HMDB0030017
HETATM    1  C1  UNL     1      -9.452  -0.306  -1.321  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.586   0.199  -0.215  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.644  -0.480   1.081  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.800   1.235  -0.443  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.893   1.835   0.563  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.446   1.776   0.092  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.986   0.391  -0.140  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.953  -0.653   0.901  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.566   0.036  -1.365  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.098  -1.314  -1.667  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.665  -1.355  -2.136  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.686  -0.844  -1.168  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.720   0.553  -0.680  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.720  -1.669  -0.717  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.308  -1.244   0.259  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.697  -1.356  -0.289  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.672  -0.900   0.768  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.773  -1.582   2.088  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.479   0.131   0.547  1.00  0.00           C  
HETATM   20  C20 UNL     1       4.459   0.643   1.515  1.00  0.00           C  
HETATM   21  C21 UNL     1       5.848   0.621   0.992  1.00  0.00           C  
HETATM   22  C22 UNL     1       6.834  -0.030   1.577  1.00  0.00           C  
HETATM   23  C23 UNL     1       6.610  -0.800   2.826  1.00  0.00           C  
HETATM   24  C24 UNL     1       8.199  -0.031   1.030  1.00  0.00           C  
HETATM   25  O1  UNL     1       9.142  -0.658   1.595  1.00  0.00           O  
HETATM   26  C25 UNL     1       8.540   0.688  -0.191  1.00  0.00           C  
HETATM   27  C26 UNL     1       9.832   0.672  -0.686  1.00  0.00           C  
HETATM   28  C27 UNL     1      10.116   1.358  -1.833  1.00  0.00           C  
HETATM   29  C28 UNL     1       9.122   2.053  -2.481  1.00  0.00           C  
HETATM   30  C29 UNL     1       7.826   2.062  -1.973  1.00  0.00           C  
HETATM   31  C30 UNL     1       7.521   1.375  -0.815  1.00  0.00           C  
HETATM   32  C31 UNL     1       6.180   1.355  -0.247  1.00  0.00           C  
HETATM   33  O2  UNL     1       5.266   1.987  -0.831  1.00  0.00           O  
HETATM   34  H1  UNL     1      -8.942  -0.306  -2.289  1.00  0.00           H  
HETATM   35  H2  UNL     1     -10.315   0.413  -1.412  1.00  0.00           H  
HETATM   36  H3  UNL     1      -9.909  -1.285  -1.079  1.00  0.00           H  
HETATM   37  H4  UNL     1      -9.655  -0.972   1.188  1.00  0.00           H  
HETATM   38  H5  UNL     1      -8.574   0.192   1.960  1.00  0.00           H  
HETATM   39  H6  UNL     1      -7.923  -1.341   1.156  1.00  0.00           H  
HETATM   40  H7  UNL     1      -7.785   1.717  -1.430  1.00  0.00           H  
HETATM   41  H8  UNL     1      -7.111   2.935   0.688  1.00  0.00           H  
HETATM   42  H9  UNL     1      -6.983   1.393   1.553  1.00  0.00           H  
HETATM   43  H10 UNL     1      -5.392   2.360  -0.832  1.00  0.00           H  
HETATM   44  H11 UNL     1      -4.763   2.253   0.820  1.00  0.00           H  
HETATM   45  H12 UNL     1      -5.590  -1.544   0.630  1.00  0.00           H  
HETATM   46  H13 UNL     1      -3.915  -0.978   1.151  1.00  0.00           H  
HETATM   47  H14 UNL     1      -5.385  -0.259   1.844  1.00  0.00           H  
HETATM   48  H15 UNL     1      -4.566   0.761  -2.196  1.00  0.00           H  
HETATM   49  H16 UNL     1      -4.706  -1.682  -2.546  1.00  0.00           H  
HETATM   50  H17 UNL     1      -4.295  -2.052  -0.867  1.00  0.00           H  
HETATM   51  H18 UNL     1      -2.376  -2.390  -2.435  1.00  0.00           H  
HETATM   52  H19 UNL     1      -2.618  -0.779  -3.101  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.688   0.996  -0.780  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.397   1.167  -1.318  1.00  0.00           H  
HETATM   55  H22 UNL     1      -2.014   0.664   0.364  1.00  0.00           H  
HETATM   56  H23 UNL     1      -0.715  -2.686  -1.100  1.00  0.00           H  
HETATM   57  H24 UNL     1       0.273  -1.876   1.189  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.151  -0.202   0.601  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.866  -0.742  -1.185  1.00  0.00           H  
HETATM   60  H27 UNL     1       1.906  -2.426  -0.577  1.00  0.00           H  
HETATM   61  H28 UNL     1       2.675  -0.814   2.868  1.00  0.00           H  
HETATM   62  H29 UNL     1       1.936  -2.291   2.244  1.00  0.00           H  
HETATM   63  H30 UNL     1       3.734  -2.153   2.136  1.00  0.00           H  
HETATM   64  H31 UNL     1       3.377   0.607  -0.439  1.00  0.00           H  
HETATM   65  H32 UNL     1       4.424   0.153   2.489  1.00  0.00           H  
HETATM   66  H33 UNL     1       4.198   1.724   1.723  1.00  0.00           H  
HETATM   67  H34 UNL     1       6.123  -0.097   3.553  1.00  0.00           H  
HETATM   68  H35 UNL     1       7.574  -1.145   3.259  1.00  0.00           H  
HETATM   69  H36 UNL     1       6.010  -1.695   2.646  1.00  0.00           H  
HETATM   70  H37 UNL     1      10.614   0.115  -0.161  1.00  0.00           H  
HETATM   71  H38 UNL     1      11.143   1.322  -2.191  1.00  0.00           H  
HETATM   72  H39 UNL     1       9.365   2.584  -3.377  1.00  0.00           H  
HETATM   73  H40 UNL     1       7.041   2.613  -2.487  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4    4
CONECT    3   37   38   39
CONECT    4    5   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8    9    9
CONECT    8   45   46   47
CONECT    9   10   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   14   14
CONECT   13   53   54   55
CONECT   14   15   56
CONECT   15   16   57   58
CONECT   16   17   59   60
CONECT   17   18   19   19
CONECT   18   61   62   63
CONECT   19   20   64
CONECT   20   21   65   66
CONECT   21   22   22   32
CONECT   22   23   24
CONECT   23   67   68   69
CONECT   24   25   25   26
CONECT   26   27   27   31
CONECT   27   28   70
CONECT   28   29   29   71
CONECT   29   30   72
CONECT   30   31   31   73
CONECT   31   32
CONECT   32   33   33
END

HMDB0030017
     RDKit          3D
Menatetrenone
 73 74  0  0  0  0  0  0  0  0999 V2000
   -9.4523   -0.3062   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5857    0.1989   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6441   -0.4797    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    1.2349   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.8355    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4458    1.7756    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    0.3906   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -0.6532    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5662    0.0360   -1.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0980   -1.3140   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651   -1.3548   -2.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861   -0.8442   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203    0.5528   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -1.6692   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -1.2441    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966   -1.3560   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -0.9002    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -1.5816    2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795    0.1310    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    0.6428    1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.6211    0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8339   -0.0305    1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -0.8004    2.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1985   -0.0311    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1425   -0.6584    1.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400    0.6882   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8323    0.6722   -0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1163    1.3581   -1.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220    2.0535   -2.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    2.0619   -1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5213    1.3749   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802    1.3550   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2657    1.9866   -0.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9423   -0.3055   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3153    0.4133   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9094   -1.2847   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6550   -0.9720    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    0.1917    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9226   -1.3411    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7851    1.7169   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1109    2.9350    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9833    1.3928    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3925    2.3602   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634    2.2534    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5901   -1.5437    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149   -0.9780    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3849   -0.2585    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    0.7608   -2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7056   -1.6818   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.0523   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -2.3904   -2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.7788   -3.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    0.9959   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    1.1667   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.6638    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -2.6863   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -1.8758    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -0.2023    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -0.7418   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -2.4265   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6751   -0.8140    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -2.2914    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343   -2.1533    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767    0.6068   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4237    0.1528    2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.7241    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228   -0.0966    3.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5743   -1.1447    3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -1.6949    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6142    0.1149   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430    1.3221   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3649    2.5839   -3.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0406    2.6133   -2.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 21  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 13 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 18 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
M  END

Synonyms

Value	Source
2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinone	ChEBI
2-Methyl-3-geranylgeranyl-1,4-naphthoquinone	ChEBI
2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinone	ChEBI
Menaquinone 4	ChEBI
Menaquinone K4	ChEBI
Menatetrenona	ChEBI
Menatetrenonum	ChEBI
MK-4	ChEBI
MK4	ChEBI
Vitamin K2(20)	ChEBI
Vitamin MK 4	ChEBI
Vitamin K2	Kegg
Menaquinone-4	ChEBI
(e,e,e)-Isomer OF menatetrenone	MeSH, HMDB
2-Methyl-3-all-trans-tetraprenyl-1,4-naphthoquinone	MeSH, HMDB
Kefton-2	MeSH, HMDB
Vitamin MK-4	MeSH, HMDB
Vitamin K 2	MeSH
Vitamin K quinone	MeSH
Menaquinone	MeSH
Menaquinones	MeSH

Molecular Formula

C₃₁H₄₀O₂

Average Mass

444.659

Monoisotopic Mass

444.302830528

IUPAC Name

2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1,4-dihydronaphthalene-1,4-dione

Traditional Name

menatetrenone

CAS Registry Number

863-61-6

SMILES

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(=O)C2=CC=CC=C2C1=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C31H40O2/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/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

InChI Key

DKHGMERMDICWDU-GHDNBGIDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Menaquinones

Alternative Parents

Substituents

Menaquinone
Diterpenoid
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

menaquinone (CHEBI:78277 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00049 g/L	ALOGPS
logP	7.24	ALOGPS
logP	8.48	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	145.51 m³·mol⁻¹	ChemAxon
Polarizability	54.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193201	NAD(P)H dehydrogenase [quinone] 1	Unknown	P15559	Homo sapiens
MMDBp0193465	Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	8	Human ; Human supragingival plaque; Human feces; Human subgingival plaque; Human saliva	Microbial culture
Bacteria/Eubacteria	Bacteroidetes	6	Human feces; Human ; Human urine; Human stool; Human saliva; Human mucosa; Human supragingival plaque; Human gastric fluid; Human subgingival plaque; Human sputum	Microbial culture
Bacteria/Eubacteria	Proteobacteria	3	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Microbial culture
Bacteria/Eubacteria	Firmicutes	11	Human saliva; Human ; Human feces; Human subgingival plaque; Human supragingival plaque	Microbial culture

Exposure Sources

Food Exposures

Source Type	Source Sub-type	Source Name	Data Source	Reference
Animal	Not Available	American lobster	FooDB	34893796
Animal	Not Available	Atlantic halibut	FooDB	34893796
Animal	Not Available	Atlantic salmon	FooDB	34893796
Animal	Not Available	Channel catfish	FooDB	34893796
Animal	Not Available	Chinook salmon	FooDB	34893796
Animal	Not Available	Chum salmon	FooDB	34893796
Animal	Not Available	Clawed lobster	FooDB	34893796
Animal	Not Available	Eastern oyster	FooDB	34893796
Animal	Not Available	Flatfish	FooDB	34893796
Animal	Not Available	Gadiformes	FooDB	34893796
Animal	Not Available	Hippoglossus (common halibut)	FooDB	34893796
Animal	Not Available	Lemon sole	FooDB	34893796
Animal	Not Available	Mollusks	FooDB	34893796
Animal	Not Available	Pacific cod	FooDB	34893796
Animal	Not Available	Pacific halibut	FooDB	34893796
Animal	Not Available	Pacific ocean perch	FooDB	34893796
Animal	Not Available	Pacific rockfish	FooDB	34893796
Animal	Not Available	Pollock	FooDB	34893796
Animal	Not Available	Rainbow trout	FooDB	34893796
Animal	Not Available	Scallop	FooDB	34893796
Animal	Not Available	Sheefish	FooDB	34893796
Animal	Not Available	Smelt	FooDB	34893796
Animal	Not Available	Sockeye salmon	FooDB	34893796
Animal	Not Available	True sole	FooDB	34893796
Animal	Not Available	Whitefish	FooDB	34893796
Plant	Not Available	Amaranth	FooDB	34893796
Plant	Not Available	Cauliflower	FooDB	34893796
Plant	Not Available	Feijoa	FooDB	34893796
Plant	Not Available	Kale	FooDB	34893796
Plant	Not Available	Lambsquarters	FooDB	34893796
Plant	Not Available	Maitake	FooDB	34893796
Plant	Not Available	Oyster mushroom	FooDB	34893796
Plant	Not Available	Prairie turnip	FooDB	34893796
Plant	Not Available	Quinoa	FooDB	34893796
Plant	Not Available	Soy bean	FooDB	34893796
Plant	Not Available	Teff	FooDB	34893796
Plant	Not Available	Wasabi	FooDB	34893796
Plant	Bean	Common bean	FooDB	34893796
Plant	Cocoa products	Cocoa bean	FooDB	34893796
Animal	Egg	Whitefish	FooDB	34893796
Plant	Fruit	Alaska blueberry	FooDB	34893796
Plant	Fruit	Common chokecherry	FooDB	34893796
Plant	Fruit	European plum	FooDB	34893796
Plant	Fruit	Garden tomato	FooDB	34893796
Plant	Fruit	Garden tomato (var.)	FooDB	34893796
Plant	Fruit	Plains prickly pear	FooDB	34893796
Plant	Fruit	Rose hip	FooDB	34893796
Plant	Fruit	Salmonberry	FooDB	34893796
Animal	Milk	Cow	FooDB	34893796
Plant	Oil	Canola oil	FooDB	34893796
Plant	Oil	Coconut oil	FooDB	34893796
Plant	Oil	Flaxseed	FooDB	34893796
Plant	Seed	Amaranth	FooDB	34893796
Plant	Seed	Sunburst squash (pattypan squash)	FooDB	34893796
Plant	Seed	Winter squash	FooDB	34893796
Plant	Shoot	Narrowleaf cattail	FooDB	34893796
Animal	Meat	See All	FooDB	34893796

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0030017

DrugBank ID

DB12148

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029792

KNApSAcK ID

Not Available

Chemspider ID

4445530

KEGG Compound ID

C00828

BioCyc ID

CPD-9726

BiGG ID

Not Available

Wikipedia Link

Menatetrenone

METLIN ID

Not Available

PubChem Compound

5282367

PDB ID

Not Available

ChEBI ID

78277

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Menatetrenone (MMDBc0000274)

MOL for #<Metabolite:0x00007f920027b138>

3D MOL for #<Metabolite:0x00007f920027b138>

3D SDF for #<Metabolite:0x00007f920027b138>

3D-SDF for #<Metabolite:0x00007f920027b138>

PDB for #<Metabolite:0x00007f920027b138>

3D PDB for #<Metabolite:0x00007f920027b138>

SMILES for #<Metabolite:0x00007f920027b138>

INCHI for #<Metabolite:0x00007f920027b138>

Structure for #<Metabolite:0x00007f920027b138>

3D Structure for #<Metabolite:0x00007f920027b138>