MiMeDB: Showing metabocard for Demethylphylloquinone (MMDBc0049894)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:42 UTC

Update Date

2024-04-30 20:40:05 UTC

Metabolite ID

MMDBc0049894

Metabolite Identification

Common Name

Demethylphylloquinone

Description

Demethylphylloquinone is a form of vitamin K that occurs in nature as part of a series of compounds with a common 2-methyl-1,4 naphthoquinone nucleus and differing isoprenoid side chains at the 3 position. Vitamin K forms comprise a single major plant form, phylloquinone with a phytyl side chain and a family of bacterially synthesized menaquinones (MKs) with multiprenyl side chains. Bacterially produced menaquinones are biologically active forms of vitamin K that are present in high concentrations in the human lower bowel. Both phylloquinone and menaquinones are bioactive in hepatic gamma-carboxylation but long-chain MKs are less well absorbed. Liver stores of vitamin K are relatively small. The hepatic reserves of phylloquinone (approximately 10% of the total) are labile and turn over at a faster rate than menaquinones. Vitamin K is recognised as a factor required for normal blood coagulation, and in relation to its role in bone metabolism. Vitamin K is a substrate for a liver microsomal enzyme that catalyzes the conversion of specific glutamyl residues to gamma-carboxyglutamyl residues in a limited number of proteins. These include the vitamin K-dependent clotting factors: prothrombin (factor II), factor VII, factor IX, and factor X. In the absence of vitamin K, nonfunctional clotting factors are synthesized and hemorrhage can result. Vitamin K is a coenzyme for glutamate carboxylase, which mediates the conversion of glutamate to gamma-carboxyglutamate (Gla). There are at least three Gla proteins associated with bone tissue, of which osteocalcin is the most abundant and best known. Trabecular and cortical bone appear to contain substantial concentrations of both phylloquinone and menaquinones. (PMID: 8642453 , 8527227 , 15018483 , 1573141 ).

Structure

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


  Mrv1652309122022562D          

 32 33  0  0  0  0            999 V2000
 9966.5115 9973.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9967.9370 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9968.6506 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5115 9969.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9969.3643 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.0782 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.3643 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.7920 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5057 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2191 9972.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9972.9325 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2191 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.6479 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9974.3613 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9975.0767 9972.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9975.7901 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9975.0767 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9976.5034 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.2189 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9323 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.6456 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9323 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.0867 9972.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9964.3742 9971.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9964.3742 9971.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.0867 9970.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5113 9972.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.7988 9971.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.7988 9971.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5113 9970.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9967.2238 9971.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9967.2238 9971.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
  1 27  2  0  0  0  0
 32  2  1  0  0  0  0
 30  4  2  0  0  0  0
 26 29  2  0  0  0  0
 23 28  2  0  0  0  0
M  END

HMDB0004649
     RDKit          3D
Demethylphylloquinone
 76 77  0  0  0  0  0  0  0  0999 V2000
   -3.8844    1.0774   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    0.0809    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -0.6362    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.6848    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.0311    0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2194    0.9512    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1509    1.6179    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8943    2.5466    0.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3089    1.2911   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2038    1.9398   -1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3085    1.5824   -3.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5021    0.5679   -3.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -0.0703   -2.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4920    0.2712   -1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -0.3860   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8262   -1.3238   -0.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.0547    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0854    1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147   -1.1301    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394   -1.4710    0.3320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3180   -2.8026   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -1.2996    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739   -2.1744    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -2.2125    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562   -1.0345    1.4605 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0679   -0.2674    2.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4253   -0.1016    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    1.0565    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    2.0589   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087    1.6057   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560    2.9053   -2.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.6466   -2.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400    0.7225   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    1.9187   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    1.6030    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -1.3523    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8602   -1.7827    1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7372   -0.3237    2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1393    1.2329    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8286    2.7418   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0206    2.1092   -3.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5753    0.2857   -4.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0056   -0.8536   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    0.9109    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.4015   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404   -2.0887    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -0.7935    2.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621   -0.1676    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -1.8921    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636   -0.7112   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -3.1232   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -2.7546   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943   -3.6049    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -1.5847   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -0.2092    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -3.2336    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -2.0761    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -3.0665    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -2.6622    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3470   -1.4698    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177    0.2142    3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.5833    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7549   -0.8790    3.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9947   -0.7197   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967    0.2320   -0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848    1.5679    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2589    0.6951    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0453    2.9791    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    2.5136   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361    1.2680   -1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771    3.0218   -2.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    3.7577   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1511    2.7103   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8812   -0.3899   -2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4977    1.0440   -3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3978    0.5949   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
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 15 16  2  0
  2 17  1  0
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 15  5  1  0
 14  9  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
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 17 44  1  0
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 19 48  1  0
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 20 50  1  6
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 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
M  END


  Mrv1652309122022562D          

 32 33  0  0  0  0            999 V2000
 9966.5115 9973.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9967.9370 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9968.6506 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5115 9969.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9969.3643 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.0782 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.3643 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.7920 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5057 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2191 9972.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9972.9325 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2191 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.6479 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9974.3613 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9975.0767 9972.3094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9975.7901 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9975.0767 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9976.5034 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.2189 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9323 9972.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.6456 9971.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9323 9973.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.0867 9972.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9964.3742 9971.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9964.3742 9971.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.0867 9970.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5113 9972.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.7988 9971.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9965.7988 9971.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9966.5113 9970.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9967.2238 9971.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9967.2238 9971.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
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  9 10  1  0  0  0  0
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  1 27  2  0  0  0  0
 32  2  1  0  0  0  0
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 26 29  2  0  0  0  0
 23 28  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049894

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24H,8-16,20H2,1-5H3/b25-19+/t23-,24-/m1/s1

> <INCHI_KEY>
UDYIPZFWVJJQJF-KQPZCCJBSA-N

> <FORMULA>
C30H44O2

> <MOLECULAR_WEIGHT>
436.68

> <EXACT_MASS>
436.334130657

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.22633794501712

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
8.38

> <JCHEM_LOGP>
9.300895319

> <ALOGPS_LOGS>
-7.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.479469686844748

> <JCHEM_PKA_STRONGEST_BASIC>
-7.173838497036545

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
138.59969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phytyl-1,4-naphthoquinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004649
     RDKit          3D
Demethylphylloquinone
 76 77  0  0  0  0  0  0  0  0999 V2000
   -3.8844    1.0774   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    0.0809    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -0.6362    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.6848    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.0311    0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2194    0.9512    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1509    1.6179    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8943    2.5466    0.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3089    1.2911   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2038    1.9398   -1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3085    1.5824   -3.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5021    0.5679   -3.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -0.0703   -2.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4920    0.2712   -1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -0.3860   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8262   -1.3238   -0.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.0547    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0854    1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147   -1.1301    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394   -1.4710    0.3320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3180   -2.8026   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -1.2996    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739   -2.1744    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -2.2125    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562   -1.0345    1.4605 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0679   -0.2674    2.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4253   -0.1016    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    1.0565    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    2.0589   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087    1.6057   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560    2.9053   -2.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.6466   -2.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400    0.7225   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    1.9187   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    1.6030    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -1.3523    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8602   -1.7827    1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7372   -0.3237    2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1393    1.2329    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8286    2.7418   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0206    2.1092   -3.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5753    0.2857   -4.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0056   -0.8536   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    0.9109    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.4015   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404   -2.0887    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -0.7935    2.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621   -0.1676    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -1.8921    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636   -0.7112   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -3.1232   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -2.7546   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943   -3.6049    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -1.5847   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -0.2092    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -3.2336    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -2.0761    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -3.0665    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -2.6622    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3470   -1.4698    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177    0.2142    3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.5833    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7549   -0.8790    3.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9947   -0.7197   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967    0.2320   -0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848    1.5679    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2589    0.6951    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0453    2.9791    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    2.5136   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361    1.2680   -1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771    3.0218   -2.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    3.7577   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1511    2.7103   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8812   -0.3899   -2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4977    1.0440   -3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3978    0.5949   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 15  5  1  0
 14  9  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
M  END

HEADER    PROTEIN                                 12-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-20         0                                  
HETATM    1  O   UNK     0    8604.1558616.517   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8606.8168614.978   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8608.1488614.204   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8604.1558610.342   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8609.4808614.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8610.8138614.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8609.4808616.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8612.1458614.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8613.4778614.204   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8614.8098614.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8616.1418614.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8614.8098616.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8617.4768614.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8618.8088614.204   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8620.1438614.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8621.4758614.204   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8620.1438616.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8622.8068614.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8624.1428614.204   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8625.4748614.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8626.8058614.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8625.4748616.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8601.4958614.966   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8600.1658614.198   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8600.1658612.662   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8601.4958611.894   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8604.1548614.966   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8602.8248614.198   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8602.8248612.662   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8604.1548611.895   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8605.4848612.662   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8605.4848614.198   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2    3   32                                                       
CONECT    3    2    5                                                       
CONECT    4   30                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5    8                                                       
CONECT    7    5                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24   28                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   29                                                       
CONECT   27   28   32    1                                                  
CONECT   28   27   29   23                                                  
CONECT   29   28   30   26                                                  
CONECT   30   29   31    4                                                  
CONECT   31   30   32                                                       
CONECT   32   27   31    2                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0004649
HETATM    1  C1  UNL     1      -3.884   1.077  -0.048  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.322   0.081   0.876  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.067  -0.636   1.668  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.508  -0.685   1.869  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.426  -0.031   0.964  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.219   0.951   1.414  1.00  0.00           C  
HETATM    7  C7  UNL     1      -8.151   1.618   0.529  1.00  0.00           C  
HETATM    8  O1  UNL     1      -8.894   2.547   0.959  1.00  0.00           O  
HETATM    9  C8  UNL     1      -8.309   1.291  -0.882  1.00  0.00           C  
HETATM   10  C9  UNL     1      -9.204   1.940  -1.707  1.00  0.00           C  
HETATM   11  C10 UNL     1      -9.308   1.582  -3.042  1.00  0.00           C  
HETATM   12  C11 UNL     1      -8.502   0.568  -3.527  1.00  0.00           C  
HETATM   13  C12 UNL     1      -7.614  -0.070  -2.692  1.00  0.00           C  
HETATM   14  C13 UNL     1      -7.492   0.271  -1.352  1.00  0.00           C  
HETATM   15  C14 UNL     1      -6.564  -0.386  -0.457  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.826  -1.324  -0.915  1.00  0.00           O  
HETATM   17  C15 UNL     1      -1.813  -0.055   0.833  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.294  -1.085   1.773  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.215  -1.130   1.678  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.739  -1.471   0.332  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.318  -2.803  -0.194  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.273  -1.300   0.230  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.974  -2.174   1.197  1.00  0.00           C  
HETATM   24  C22 UNL     1       4.437  -2.213   1.219  1.00  0.00           C  
HETATM   25  C23 UNL     1       5.256  -1.034   1.461  1.00  0.00           C  
HETATM   26  C24 UNL     1       5.068  -0.267   2.711  1.00  0.00           C  
HETATM   27  C25 UNL     1       5.425  -0.102   0.277  1.00  0.00           C  
HETATM   28  C26 UNL     1       6.284   1.056   0.643  1.00  0.00           C  
HETATM   29  C27 UNL     1       6.508   2.059  -0.395  1.00  0.00           C  
HETATM   30  C28 UNL     1       7.209   1.606  -1.629  1.00  0.00           C  
HETATM   31  C29 UNL     1       7.356   2.905  -2.487  1.00  0.00           C  
HETATM   32  C30 UNL     1       6.469   0.647  -2.491  1.00  0.00           C  
HETATM   33  H1  UNL     1      -4.040   0.722  -1.085  1.00  0.00           H  
HETATM   34  H2  UNL     1      -3.109   1.919  -0.205  1.00  0.00           H  
HETATM   35  H3  UNL     1      -4.706   1.603   0.423  1.00  0.00           H  
HETATM   36  H4  UNL     1      -3.460  -1.352   2.320  1.00  0.00           H  
HETATM   37  H5  UNL     1      -5.860  -1.783   1.934  1.00  0.00           H  
HETATM   38  H6  UNL     1      -5.737  -0.324   2.913  1.00  0.00           H  
HETATM   39  H7  UNL     1      -7.139   1.233   2.473  1.00  0.00           H  
HETATM   40  H8  UNL     1      -9.829   2.742  -1.286  1.00  0.00           H  
HETATM   41  H9  UNL     1     -10.021   2.109  -3.668  1.00  0.00           H  
HETATM   42  H10 UNL     1      -8.575   0.286  -4.552  1.00  0.00           H  
HETATM   43  H11 UNL     1      -7.006  -0.854  -3.109  1.00  0.00           H  
HETATM   44  H12 UNL     1      -1.343   0.911   1.051  1.00  0.00           H  
HETATM   45  H13 UNL     1      -1.602  -0.401  -0.223  1.00  0.00           H  
HETATM   46  H14 UNL     1      -1.740  -2.089   1.598  1.00  0.00           H  
HETATM   47  H15 UNL     1      -1.562  -0.794   2.808  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.662  -0.168   1.995  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.583  -1.892   2.409  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.364  -0.711  -0.419  1.00  0.00           H  
HETATM   51  H19 UNL     1       1.101  -3.123  -0.943  1.00  0.00           H  
HETATM   52  H20 UNL     1      -0.631  -2.755  -0.792  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.294  -3.605   0.559  1.00  0.00           H  
HETATM   54  H22 UNL     1       2.536  -1.585  -0.800  1.00  0.00           H  
HETATM   55  H23 UNL     1       2.394  -0.209   0.444  1.00  0.00           H  
HETATM   56  H24 UNL     1       2.638  -3.234   0.936  1.00  0.00           H  
HETATM   57  H25 UNL     1       2.562  -2.076   2.248  1.00  0.00           H  
HETATM   58  H26 UNL     1       4.725  -3.067   1.925  1.00  0.00           H  
HETATM   59  H27 UNL     1       4.761  -2.662   0.216  1.00  0.00           H  
HETATM   60  H28 UNL     1       6.347  -1.470   1.561  1.00  0.00           H  
HETATM   61  H29 UNL     1       6.018   0.214   3.023  1.00  0.00           H  
HETATM   62  H30 UNL     1       4.343   0.583   2.560  1.00  0.00           H  
HETATM   63  H31 UNL     1       4.755  -0.879   3.581  1.00  0.00           H  
HETATM   64  H32 UNL     1       5.995  -0.720  -0.471  1.00  0.00           H  
HETATM   65  H33 UNL     1       4.497   0.232  -0.176  1.00  0.00           H  
HETATM   66  H34 UNL     1       5.785   1.568   1.533  1.00  0.00           H  
HETATM   67  H35 UNL     1       7.259   0.695   1.088  1.00  0.00           H  
HETATM   68  H36 UNL     1       7.045   2.979   0.040  1.00  0.00           H  
HETATM   69  H37 UNL     1       5.497   2.514  -0.652  1.00  0.00           H  
HETATM   70  H38 UNL     1       8.236   1.268  -1.452  1.00  0.00           H  
HETATM   71  H39 UNL     1       6.377   3.022  -2.990  1.00  0.00           H  
HETATM   72  H40 UNL     1       7.527   3.758  -1.830  1.00  0.00           H  
HETATM   73  H41 UNL     1       8.151   2.710  -3.229  1.00  0.00           H  
HETATM   74  H42 UNL     1       6.881  -0.390  -2.512  1.00  0.00           H  
HETATM   75  H43 UNL     1       6.498   1.044  -3.573  1.00  0.00           H  
HETATM   76  H44 UNL     1       5.398   0.595  -2.286  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3   17
CONECT    3    4   36
CONECT    4    5   37   38
CONECT    5    6    6   15
CONECT    6    7   39
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   43
CONECT   14   15
CONECT   15   16   16
CONECT   17   18   44   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   22   50
CONECT   21   51   52   53
CONECT   22   23   54   55
CONECT   23   24   56   57
CONECT   24   25   58   59
CONECT   25   26   27   60
CONECT   26   61   62   63
CONECT   27   28   64   65
CONECT   28   29   66   67
CONECT   29   30   68   69
CONECT   30   31   32   70
CONECT   31   71   72   73
CONECT   32   74   75   76
END

HMDB0004649
     RDKit          3D
Demethylphylloquinone
 76 77  0  0  0  0  0  0  0  0999 V2000
   -3.8844    1.0774   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    0.0809    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -0.6362    1.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.6848    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.0311    0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2194    0.9512    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1509    1.6179    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8943    2.5466    0.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3089    1.2911   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2038    1.9398   -1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3085    1.5824   -3.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5021    0.5679   -3.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -0.0703   -2.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4920    0.2712   -1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -0.3860   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8262   -1.3238   -0.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.0547    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0854    1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147   -1.1301    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394   -1.4710    0.3320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3180   -2.8026   -0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -1.2996    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739   -2.1744    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -2.2125    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562   -1.0345    1.4605 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0679   -0.2674    2.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4253   -0.1016    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837    1.0565    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    2.0589   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087    1.6057   -1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560    2.9053   -2.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.6466   -2.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400    0.7225   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    1.9187   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    1.6030    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -1.3523    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8602   -1.7827    1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7372   -0.3237    2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1393    1.2329    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8286    2.7418   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0206    2.1092   -3.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5753    0.2857   -4.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0056   -0.8536   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    0.9109    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.4015   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404   -2.0887    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -0.7935    2.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621   -0.1676    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -1.8921    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636   -0.7112   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -3.1232   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -2.7546   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943   -3.6049    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -1.5847   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -0.2092    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -3.2336    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -2.0761    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -3.0665    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -2.6622    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3470   -1.4698    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177    0.2142    3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.5833    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7549   -0.8790    3.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9947   -0.7197   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967    0.2320   -0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848    1.5679    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2589    0.6951    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0453    2.9791    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    2.5136   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361    1.2680   -1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771    3.0218   -2.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    3.7577   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1511    2.7103   -3.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8812   -0.3899   -2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4977    1.0440   -3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3978    0.5949   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 15  5  1  0
 14  9  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
M  END

Synonyms

Value	Source
PHNQ CPD	HMDB
2-Phytyl-1,4-naphthoquinone	HMDB
2-[(2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecenyl]-1,4-naphthalenedione	HMDB
Nor-alpha-phylloquinone	HMDB
Nor-α-phylloquinone	HMDB
Norvitamin K	HMDB
Demethylphylloquinone	ChEBI

Molecular Formula

C₃₀H₄₄O₂

Average Mass

436.68

Monoisotopic Mass

436.334130657

IUPAC Name

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

Traditional Name

2-phytyl-1,4-naphthoquinone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H44O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24H,8-16,20H2,1-5H3/b25-19+/t23-,24-/m1/s1

InChI Key

UDYIPZFWVJJQJF-KQPZCCJBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

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

phylloquinones (CHEBI:31087 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.7e-05 g/L	ALOGPS
logP	8.38	ALOGPS
logP	9.3	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	12.48	ChemAxon
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	14	ChemAxon
Refractivity	138.6 m³·mol⁻¹	ChemAxon
Polarizability	54.23 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0125900000-60ee1796aba3070aecfd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4912000000-0c3cb0b67fd0cded41a8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-2910000000-1f5a699bad595e9e1781	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000900000-386f84e878751722959d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-0900700000-4029e6872c46a289779a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fl1-0968300000-5c6ffbc09a6370adf5ae	2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007527	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available		VMH	30371894

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	Proteobacteria	141	Human feces; Human sputum; Human unknown; Pig ; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	43	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	94	Human feces; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	149	Human feces; Human ; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	13	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	nah	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004649

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023391

KNApSAcK ID

Not Available

Chemspider ID

26333244

KEGG Compound ID

Not Available

BioCyc ID

CPD-6947

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56927684

PDB ID

Not Available

ChEBI ID

31087

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Suttie JW: Vitamin K and human nutrition. J Am Diet Assoc. 1992 May;92(5):585-90. [PubMed:1573141 ]
Suttie JW: The importance of menaquinones in human nutrition. Annu Rev Nutr. 1995;15:399-417. doi: 10.1146/annurev.nu.15.070195.002151. [PubMed:8527227 ]
Shearer MJ, Bach A, Kohlmeier M: Chemistry, nutritional sources, tissue distribution and metabolism of vitamin K with special reference to bone health. J Nutr. 1996 Apr;126(4 Suppl):1181S-6S. doi: 10.1093/jn/126.suppl_4.1181S. [PubMed:8642453 ]
Bugel S: Vitamin K and bone health. Proc Nutr Soc. 2003 Nov;62(4):839-43. doi: 10.1079/PNS2003305. [PubMed:15018483 ]

Showing metabocard for Demethylphylloquinone (MMDBc0049894)

MOL for #<Metabolite:0x00007fecf2104488>

3D MOL for #<Metabolite:0x00007fecf2104488>

3D SDF for #<Metabolite:0x00007fecf2104488>

3D-SDF for #<Metabolite:0x00007fecf2104488>

PDB for #<Metabolite:0x00007fecf2104488>

3D PDB for #<Metabolite:0x00007fecf2104488>

SMILES for #<Metabolite:0x00007fecf2104488>

INCHI for #<Metabolite:0x00007fecf2104488>

Structure for #<Metabolite:0x00007fecf2104488>

3D Structure for #<Metabolite:0x00007fecf2104488>