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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 23:06:49 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004649

Secondary Accession Numbers

HMDB04649

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
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 11 13  1  0  0  0  0
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 16 18  1  0  0  0  0
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 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
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   -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
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    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
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    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
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    2.5361   -1.5847   -0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    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
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  1  2  1  0
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 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
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 30  4  2  0  0  0  0
 26 29  2  0  0  0  0
 23 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004649

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₃₀H₄₄O₂

Average Molecular Weight

436.68

Monoisotopic Molecular Weight

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

34625-86-0

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004649)

Source

Endogenous

Endogenous (HMDB: HMDB0004649)

Animal

Animal (HMDB: HMDB0004649)

Microbe

Microbe (HMDB: HMDB0004649)

Exogenous

Food

Food (HMDB: HMDB0004649)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Exogenous (HMDB: HMDB0004649)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0004649)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0004649)
Phylloquinol Biosynthesis (PathBank: SMP0012040)

Lipid metabolism pathway (HMDB: HMDB0004649)

Cellular process

Cell signaling (HMDB: HMDB0004649)

Biochemical process

Lipid transport (HMDB: HMDB0004649)

Role

Biological role

Energy source (HMDB: HMDB0004649)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004649)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	8.719	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	212.315	30932474
DeepCCS	[M-H]-	209.957	30932474
DeepCCS	[M-2H]-	242.841	30932474
DeepCCS	[M+Na]+	218.832	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	11.11 minutes	32390414
Predicted by Siyang on May 30, 2022	35.6832 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4055.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1181.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	439.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	653.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	820.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1672.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1529.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	172.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3123.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1132.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2896.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1201.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	831.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	842.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	988.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demethylphylloquinone	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O	4267.0	Standard polar	33892256
Demethylphylloquinone	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O	3311.8	Standard non polar	33892256
Demethylphylloquinone	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=O	3394.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylphylloquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylphylloquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 10V, Positive-QTOF	splash10-000i-0125900000-60ee1796aba3070aecfd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 20V, Positive-QTOF	splash10-00di-4912000000-0c3cb0b67fd0cded41a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 40V, Positive-QTOF	splash10-05fr-2910000000-1f5a699bad595e9e1781	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 10V, Negative-QTOF	splash10-000i-0000900000-386f84e878751722959d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 20V, Negative-QTOF	splash10-00dr-0900700000-4029e6872c46a289779a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylphylloquinone 40V, Negative-QTOF	splash10-0fl1-0968300000-5c6ffbc09a6370adf5ae	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

DMPHQNO

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:8642453 ]
Suttie JW: The importance of menaquinones in human nutrition. Annu Rev Nutr. 1995;15:399-417. [PubMed:8527227 ]
Bugel S: Vitamin K and bone health. Proc Nutr Soc. 2003 Nov;62(4):839-43. [PubMed:15018483 ]
Suttie JW: Vitamin K and human nutrition. J Am Diet Assoc. 1992 May;92(5):585-90. [PubMed:1573141 ]

Showing metabocard for Demethylphylloquinone (HMDB0004649)

MOL for HMDB0004649 (Demethylphylloquinone)

3D MOL for HMDB0004649 (Demethylphylloquinone)

3D SDF for HMDB0004649 (Demethylphylloquinone)

3D-SDF for HMDB0004649 (Demethylphylloquinone)

PDB for HMDB0004649 (Demethylphylloquinone)

3D PDB for HMDB0004649 (Demethylphylloquinone)

SMILES for HMDB0004649 (Demethylphylloquinone)

INCHI for HMDB0004649 (Demethylphylloquinone)

Structure for HMDB0004649 (Demethylphylloquinone)

3D Structure for HMDB0004649 (Demethylphylloquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra