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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 14:02:40 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004198

Secondary Accession Numbers

HMDB0060502
HMDB04198
HMDB60502

Metabolite Identification

Common Name

Phylloquinol

Description

Phylloquinol, also known as vitamin K1 hydroquinone or reduced vitamin K1, is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione).

Structure

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


  Mrv1652309042000302D          

 33 34  0  0  1  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0025    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 12  1  0  0  0  0
  3  1  2  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  2  0  0  0  0
  7 13  1  0  0  0  0
  5  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  9  2  0  0  0  0
  9 33  1  0  0  0  0
  6 10  2  0  0  0  0
  8 10  1  0  0  0  0
 13 32  1  0  0  0  0
 32 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END

HMDB0004198
     RDKit          3D
Phylloquinol
 81 82  0  0  0  0  0  0  0  0999 V2000
    2.8700    1.3398    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970    0.0061    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601   -0.3612    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465    0.4714    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9720    0.3598   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333    1.0058   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.8977   -1.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.8403   -3.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    1.4986   -4.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2708    0.0144   -3.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9098   -0.1629   -4.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024   -0.9880   -4.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4529   -1.6414   -3.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8209   -1.4741   -2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7129   -0.6340   -2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0910   -0.4850   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5397   -1.1371    0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -0.9641    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.3771    2.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745   -0.3386    3.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.2499    2.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.3191    3.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -0.8597    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.5194    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    0.4480    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8061    0.5570    0.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2251    1.0584   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    1.2047    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1217    1.3743    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698    0.2555   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5312   -0.7636    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7459   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7474   -1.6644    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206    1.6727    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.3689    2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    2.1439    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.3926    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342    1.5340    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743    0.0659    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173    1.6787   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955    1.7122   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456    2.9687   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    2.1217   -4.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5440    0.3599   -5.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4878   -1.1171   -5.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3079   -2.2972   -3.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1725   -1.9887   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.7627    0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181   -1.8754    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.5021    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386   -1.8098    2.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -2.2821    2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -0.8644    3.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    0.4861    3.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.7791    1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    2.2906    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4816    1.5467    3.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    0.9441    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.6957    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.2689    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.0941    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.4886    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.4674    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.0307    2.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.5346    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4031    1.7860   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586    1.4581   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3961    0.7812    1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622    2.1425   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.9432    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0720   -0.3042   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4995    0.7087   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4629   -0.3853    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7088   -1.1307   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2151   -2.1167   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6793   -2.4881   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7842   -1.9825    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5848   -1.2291    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
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 12 13  1  0
 13 14  2  0
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 16 17  1  0
  2 18  1  0
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 16  5  1  0
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 30 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END


  Mrv1652309042000302D          

 33 34  0  0  1  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0025    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004198

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

> <INCHI_KEY>
BUFJIHPUGZHTHL-NKFFZRIASA-N

> <FORMULA>
C31H48O2

> <MOLECULAR_WEIGHT>
452.7116

> <EXACT_MASS>
452.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.9145022523942

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.00

> <JCHEM_LOGP>
10.793461587000001

> <ALOGPS_LOGS>
-6.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.295748341144826

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.384535443373217

> <JCHEM_PKA_STRONGEST_BASIC>
-5.995354564344162

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
144.6118

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin K hydroquinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004198
     RDKit          3D
Phylloquinol
 81 82  0  0  0  0  0  0  0  0999 V2000
    2.8700    1.3398    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970    0.0061    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601   -0.3612    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465    0.4714    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9720    0.3598   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333    1.0058   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.8977   -1.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.8403   -3.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    1.4986   -4.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2708    0.0144   -3.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9098   -0.1629   -4.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024   -0.9880   -4.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4529   -1.6414   -3.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8209   -1.4741   -2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7129   -0.6340   -2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0910   -0.4850   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5397   -1.1371    0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -0.9641    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.3771    2.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745   -0.3386    3.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.2499    2.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.3191    3.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -0.8597    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.5194    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    0.4480    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8061    0.5570    0.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2251    1.0584   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    1.2047    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1217    1.3743    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698    0.2555   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5312   -0.7636    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7459   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7474   -1.6644    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206    1.6727    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.3689    2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    2.1439    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.3926    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342    1.5340    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743    0.0659    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173    1.6787   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955    1.7122   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456    2.9687   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    2.1217   -4.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5440    0.3599   -5.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4878   -1.1171   -5.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3079   -2.2972   -3.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1725   -1.9887   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.7627    0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181   -1.8754    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.5021    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386   -1.8098    2.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -2.2821    2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -0.8644    3.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    0.4861    3.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.7791    1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    2.2906    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4816    1.5467    3.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    0.9441    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.6957    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.2689    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.0941    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.4886    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.4674    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.0307    2.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.5346    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.2062   -1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    1.7860   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586    1.4581   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7181    2.2632    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3961    0.7812    1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622    2.1425   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.9432    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0720   -0.3042   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4995    0.7087   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4629   -0.3853    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7088   -1.1307   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2151   -2.1167   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6793   -2.4881   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7842   -1.9825    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2981   -2.6340    1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5848   -1.2291    2.0792 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
  6  8  1  0
  8  9  1  0
  8 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
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 16  5  1  0
 15 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  9 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  6
 22 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.671   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.338   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.671   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.005   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.339   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.673   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.673   3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.006   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3    6                                                  
CONECT    2    1   12    9                                                  
CONECT    3    1    4    5                                                  
CONECT    4    3   11    7                                                  
CONECT    5    3    8                                                       
CONECT    6    1   10                                                       
CONECT    7    4   13    9                                                  
CONECT    8    5   10                                                       
CONECT    9    7    2   33                                                  
CONECT   10    6    8                                                       
CONECT   11    4                                                            
CONECT   12    2                                                            
CONECT   13    7   32                                                       
CONECT   14   32   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   13   14                                                       
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0004198
HETATM    1  C1  UNL     1       2.870   1.340   1.621  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.997   0.006   1.030  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.160  -0.361   0.491  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.347   0.471   0.427  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.972   0.360  -0.911  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.533   1.006  -2.029  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.360   1.898  -1.980  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.176   0.840  -3.270  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.735   1.499  -4.408  1.00  0.00           O  
HETATM   10  C9  UNL     1       7.271   0.014  -3.377  1.00  0.00           C  
HETATM   11  C10 UNL     1       7.910  -0.163  -4.603  1.00  0.00           C  
HETATM   12  C11 UNL     1       9.002  -0.988  -4.750  1.00  0.00           C  
HETATM   13  C12 UNL     1       9.453  -1.641  -3.639  1.00  0.00           C  
HETATM   14  C13 UNL     1       8.821  -1.474  -2.397  1.00  0.00           C  
HETATM   15  C14 UNL     1       7.713  -0.634  -2.261  1.00  0.00           C  
HETATM   16  C15 UNL     1       7.091  -0.485  -1.021  1.00  0.00           C  
HETATM   17  O2  UNL     1       7.540  -1.137   0.084  1.00  0.00           O  
HETATM   18  C16 UNL     1       1.853  -0.964   0.997  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.279  -1.377   2.284  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.575  -0.339   3.053  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.600   0.250   2.238  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.243   1.319   3.138  1.00  0.00           C  
HETATM   23  C21 UNL     1      -1.536  -0.860   1.904  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.707  -0.519   1.076  1.00  0.00           C  
HETATM   25  C23 UNL     1      -3.689   0.448   1.640  1.00  0.00           C  
HETATM   26  C24 UNL     1      -4.806   0.557   0.566  1.00  0.00           C  
HETATM   27  C25 UNL     1      -4.225   1.058  -0.694  1.00  0.00           C  
HETATM   28  C26 UNL     1      -6.034   1.205   1.062  1.00  0.00           C  
HETATM   29  C27 UNL     1      -7.122   1.374   0.090  1.00  0.00           C  
HETATM   30  C28 UNL     1      -7.770   0.256  -0.579  1.00  0.00           C  
HETATM   31  C29 UNL     1      -8.531  -0.764   0.158  1.00  0.00           C  
HETATM   32  C30 UNL     1      -9.086  -1.746  -0.916  1.00  0.00           C  
HETATM   33  C31 UNL     1      -7.747  -1.664   1.074  1.00  0.00           C  
HETATM   34  H1  UNL     1       1.821   1.673   1.570  1.00  0.00           H  
HETATM   35  H2  UNL     1       3.164   1.369   2.699  1.00  0.00           H  
HETATM   36  H3  UNL     1       3.423   2.144   1.065  1.00  0.00           H  
HETATM   37  H4  UNL     1       4.215  -1.393   0.058  1.00  0.00           H  
HETATM   38  H5  UNL     1       5.234   1.534   0.696  1.00  0.00           H  
HETATM   39  H6  UNL     1       6.074   0.066   1.200  1.00  0.00           H  
HETATM   40  H7  UNL     1       3.717   1.679  -1.120  1.00  0.00           H  
HETATM   41  H8  UNL     1       3.696   1.712  -2.879  1.00  0.00           H  
HETATM   42  H9  UNL     1       4.646   2.969  -2.068  1.00  0.00           H  
HETATM   43  H10 UNL     1       4.952   2.122  -4.292  1.00  0.00           H  
HETATM   44  H11 UNL     1       7.544   0.360  -5.489  1.00  0.00           H  
HETATM   45  H12 UNL     1       9.488  -1.117  -5.707  1.00  0.00           H  
HETATM   46  H13 UNL     1      10.308  -2.297  -3.709  1.00  0.00           H  
HETATM   47  H14 UNL     1       9.173  -1.989  -1.535  1.00  0.00           H  
HETATM   48  H15 UNL     1       8.280  -1.763   0.231  1.00  0.00           H  
HETATM   49  H16 UNL     1       2.218  -1.875   0.435  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.031  -0.502   0.380  1.00  0.00           H  
HETATM   51  H18 UNL     1       2.139  -1.810   2.928  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.650  -2.282   2.130  1.00  0.00           H  
HETATM   53  H20 UNL     1       0.124  -0.864   3.957  1.00  0.00           H  
HETATM   54  H21 UNL     1       1.141   0.486   3.467  1.00  0.00           H  
HETATM   55  H22 UNL     1      -0.244   0.779   1.339  1.00  0.00           H  
HETATM   56  H23 UNL     1      -1.346   2.291   2.633  1.00  0.00           H  
HETATM   57  H24 UNL     1      -0.482   1.547   3.960  1.00  0.00           H  
HETATM   58  H25 UNL     1      -2.109   0.944   3.685  1.00  0.00           H  
HETATM   59  H26 UNL     1      -0.944  -1.696   1.404  1.00  0.00           H  
HETATM   60  H27 UNL     1      -1.891  -1.269   2.905  1.00  0.00           H  
HETATM   61  H28 UNL     1      -2.331  -0.094   0.076  1.00  0.00           H  
HETATM   62  H29 UNL     1      -3.236  -1.489   0.774  1.00  0.00           H  
HETATM   63  H30 UNL     1      -3.276   1.467   1.780  1.00  0.00           H  
HETATM   64  H31 UNL     1      -4.178   0.031   2.538  1.00  0.00           H  
HETATM   65  H32 UNL     1      -5.054  -0.535   0.390  1.00  0.00           H  
HETATM   66  H33 UNL     1      -3.819   0.206  -1.283  1.00  0.00           H  
HETATM   67  H34 UNL     1      -3.403   1.786  -0.608  1.00  0.00           H  
HETATM   68  H35 UNL     1      -5.059   1.458  -1.344  1.00  0.00           H  
HETATM   69  H36 UNL     1      -5.718   2.263   1.361  1.00  0.00           H  
HETATM   70  H37 UNL     1      -6.396   0.781   1.997  1.00  0.00           H  
HETATM   71  H38 UNL     1      -6.862   2.143  -0.715  1.00  0.00           H  
HETATM   72  H39 UNL     1      -7.944   1.943   0.651  1.00  0.00           H  
HETATM   73  H40 UNL     1      -7.072  -0.304  -1.290  1.00  0.00           H  
HETATM   74  H41 UNL     1      -8.499   0.709  -1.338  1.00  0.00           H  
HETATM   75  H42 UNL     1      -9.463  -0.385   0.648  1.00  0.00           H  
HETATM   76  H43 UNL     1      -9.709  -1.131  -1.621  1.00  0.00           H  
HETATM   77  H44 UNL     1      -8.215  -2.117  -1.466  1.00  0.00           H  
HETATM   78  H45 UNL     1      -9.679  -2.488  -0.381  1.00  0.00           H  
HETATM   79  H46 UNL     1      -6.784  -1.982   0.654  1.00  0.00           H  
HETATM   80  H47 UNL     1      -8.298  -2.634   1.246  1.00  0.00           H  
HETATM   81  H48 UNL     1      -7.585  -1.229   2.079  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   18
CONECT    3    4   37
CONECT    4    5   38   39
CONECT    5    6    6   16
CONECT    6    7    8
CONECT    7   40   41   42
CONECT    8    9   10   10
CONECT    9   43
CONECT   10   11   15
CONECT   11   12   12   44
CONECT   12   13   45
CONECT   13   14   14   46
CONECT   14   15   47
CONECT   15   16   16
CONECT   16   17
CONECT   17   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   23   55
CONECT   22   56   57   58
CONECT   23   24   59   60
CONECT   24   25   61   62
CONECT   25   26   63   64
CONECT   26   27   28   65
CONECT   27   66   67   68
CONECT   28   29   69   70
CONECT   29   30   71   72
CONECT   30   31   73   74
CONECT   31   32   33   75
CONECT   32   76   77   78
CONECT   33   79   80   81
END

HMDB0004198
     RDKit          3D
Phylloquinol
 81 82  0  0  0  0  0  0  0  0999 V2000
    2.8700    1.3398    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970    0.0061    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601   -0.3612    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465    0.4714    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9720    0.3598   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333    1.0058   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.8977   -1.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.8403   -3.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    1.4986   -4.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2708    0.0144   -3.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9098   -0.1629   -4.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024   -0.9880   -4.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4529   -1.6414   -3.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8209   -1.4741   -2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7129   -0.6340   -2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0910   -0.4850   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5397   -1.1371    0.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -0.9641    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.3771    2.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5745   -0.3386    3.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.2499    2.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.3191    3.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -0.8597    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.5194    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    0.4480    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8061    0.5570    0.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2251    1.0584   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0336    1.2047    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1217    1.3743    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7698    0.2555   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5312   -0.7636    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0859   -1.7459   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7474   -1.6644    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206    1.6727    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.3689    2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    2.1439    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.3926    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342    1.5340    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743    0.0659    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173    1.6787   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955    1.7122   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456    2.9687   -2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    2.1217   -4.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5440    0.3599   -5.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4878   -1.1171   -5.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3079   -2.2972   -3.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1725   -1.9887   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.7627    0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181   -1.8754    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.5021    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386   -1.8098    2.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -2.2821    2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -0.8644    3.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    0.4861    3.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.7791    1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    2.2906    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4816    1.5467    3.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    0.9441    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.6957    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.2689    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.0941    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -1.4886    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.4674    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.0307    2.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.5346    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.2062   -1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    1.7860   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586    1.4581   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7181    2.2632    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3961    0.7812    1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622    2.1425   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9444    1.9432    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0720   -0.3042   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4995    0.7087   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4629   -0.3853    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7088   -1.1307   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2151   -2.1167   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6793   -2.4881   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7842   -1.9825    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2981   -2.6340    1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5848   -1.2291    2.0792 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
  6  8  1  0
  8  9  1  0
  8 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
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 16  5  1  0
 15 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  9 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  6
 22 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Phytonadiol	ChEBI
Vitamin K hydroquinone	ChEBI
Vitamin K1 hydroquinone	ChEBI
Reduced vitamin K1	HMDB
Dihydrovitamin K1	HMDB
Dihydroxyvitamin K	HMDB
Reduced vitamin K	HMDB
[R-[R,r-(e)]]-2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediol	HMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenediol	HMDB
(e)-2-Methyl-3-phytyl-1,4-naphthalenediol	HMDB
2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthalenediol	HMDB
2-Methyl-3-phytyl-1,4-naphthohydroquinone	HMDB
Dihydro-phylloquinone	HMDB
Reduced phylloquinone	HMDB
Α-phyllohydroquinone	HMDB
alpha-Phyllohydroquinone	HMDB
Phylloquinol	HMDB

Chemical Formula

C₃₁H₄₈O₂

Average Molecular Weight

452.7116

Monoisotopic Molecular Weight

452.36543078

IUPAC Name

2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-diol

Traditional Name

vitamin K hydroquinone

CAS Registry Number

572-96-3

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C

InChI Identifier

InChI=1S/C31H48O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

InChI Key

BUFJIHPUGZHTHL-NKFFZRIASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Prenylbenzoquinol
1-naphthol
Naphthalene
Hydroquinone
Benzenoid
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyprenylhydroquinone (CHEBI:28433 )
Vitamin K (LMPR02030030 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0060502)

Source

Endogenous

Endogenous (HMDB: HMDB0060502)

Animal

Animal (HMDB: HMDB0060502)

Exogenous

Food

Food (HMDB: HMDB0060502)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

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)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

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)

Brassica

Brassicas (FooDB: FOOD00857)

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)
Citrus (FooDB: FOOD00859)

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)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

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)

Fruits (FooDB: FOOD00871)

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)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

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

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

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

Tea

Herbal tea

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

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

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

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Exogenous (HMDB: HMDB0060502)

Process

Role

Biological role

Energy source (HMDB: HMDB0060502)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0060502)

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.9e-05 g/L	ALOGPS
logP	9	ALOGPS
logP	10.79	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	144.61 m³·mol⁻¹	ChemAxon
Polarizability	56.91 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]+	216.884	30932474
DeepCCS	[M-H]-	214.489	30932474
DeepCCS	[M-2H]-	247.371	30932474
DeepCCS	[M+Na]+	222.797	30932474
AllCCS	[M+H]+	222.2	32859911
AllCCS	[M+H-H2O]+	220.2	32859911
AllCCS	[M+NH4]+	224.0	32859911
AllCCS	[M+Na]+	224.5	32859911
AllCCS	[M-H]-	217.1	32859911
AllCCS	[M+Na-2H]-	220.0	32859911
AllCCS	[M+HCOO]-	223.3	32859911

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.	10.72 minutes	32390414
Predicted by Siyang on May 30, 2022	39.2219 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	54.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4867.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1282.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	514.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	748.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	933.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1941.2 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	1722.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	146.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3372.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1281.7 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	3325.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1228.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1040.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1028.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	904.2 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	9.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phylloquinol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C	4366.7	Standard polar	33892256
Phylloquinol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C	3352.3	Standard non polar	33892256
Phylloquinol	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C	3569.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phylloquinol,1TMS,isomer #1	C/C(=C\CC1=C(C)C(O)=C2C=CC=CC2=C1O[Si](C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3519.4	Semi standard non polar	33892256
Phylloquinol,1TMS,isomer #2	C/C(=C\CC1=C(C)C(O[Si](C)(C)C)=C2C=CC=CC2=C1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3517.9	Semi standard non polar	33892256
Phylloquinol,2TMS,isomer #1	C/C(=C\CC1=C(C)C(O[Si](C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3532.2	Semi standard non polar	33892256
Phylloquinol,1TBDMS,isomer #1	C/C(=C\CC1=C(C)C(O)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3755.0	Semi standard non polar	33892256
Phylloquinol,1TBDMS,isomer #2	C/C(=C\CC1=C(C)C(O[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3749.2	Semi standard non polar	33892256
Phylloquinol,2TBDMS,isomer #1	C/C(=C\CC1=C(C)C(O[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C	3979.4	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 - Phylloquinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-7985400000-4cfe604c94178a729cf3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phylloquinol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-3202290000-25d2205e065a0bc3f3c6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phylloquinol 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 - Phylloquinol 10V, Positive-QTOF	splash10-0udi-0231900000-da7eef794d2e18b29e5e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 20V, Positive-QTOF	splash10-05ra-4894400000-0c348ad8b15b7a428570	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 40V, Positive-QTOF	splash10-0a4i-9772200000-7096132ee959664099b9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 10V, Negative-QTOF	splash10-0udi-0000900000-dddf4ff7cce1cd10e63d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 20V, Negative-QTOF	splash10-0udi-0000900000-0e62002f1cd3fa58a876	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 40V, Negative-QTOF	splash10-00di-1922500000-1cdb8ac94dc6ec135bc1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 10V, Positive-QTOF	splash10-0udi-0213900000-8b373faac5ad9f297e5b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 20V, Positive-QTOF	splash10-0a4s-9606200000-8fc6ca059ad0776f02f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 40V, Positive-QTOF	splash10-053b-9640000000-1310e158a977feb080ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 10V, Negative-QTOF	splash10-0udi-0000900000-ce8af0c741feb6e6a8a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 20V, Negative-QTOF	splash10-0udr-0510900000-67cf209cf7be0a03a70a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phylloquinol 40V, Negative-QTOF	splash10-02tj-0629300000-4674747e6c430d2d5c93	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Vitamin K Metabolism		Not Available
Acenocoumarol Action Pathway		Not Available
Coagulation		Not Available
Enoxaparin Action Pathway		Not Available
Fondaparinux Action Pathway		Not Available

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

FDB031116

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03313

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280585

PDB ID

Not Available

ChEBI ID

28433

Food Biomarker Ontology

Not Available

VMH ID

M02829

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Masaki, Yukio; Hashimoto, Kinji; Kaji, Kenji. Synthetic studies on isoprenoidquinones. II. Syntheses of ubiquinone-10, phylloquinone, and menaquinone-4 by a chain-extending method utilizing terminally functionalized isoprenoidhydroquinones. Chemical & Pharmaceutical Bulletin (1984), 32(10), 3959-67.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tovar A, Ameho CK, Blumberg JB, Peterson JW, Smith D, Booth SL: Extrahepatic tissue concentrations of vitamin K are lower in rats fed a high vitamin E diet. Nutr Metab (Lond). 2006 Jul 20;3:29. [PubMed:16857056 ]
Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. NAD(P)H dehydrogenase [quinone] 1

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO1
Uniprot ID:: P15559
Molecular weight:: 30867.405

Reactions

Vitamin K1 + NADH + Hydrogen Ion → Phylloquinol + NAD	details

Enzyme Details

2. Vitamin K-dependent gamma-carboxylase

General function:: Involved in gamma-glutamyl carboxylase activity
Specific function:: Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:: GGCX
Uniprot ID:: P38435
Molecular weight:: 87560.065

Reactions

[Peptidyl]-4-carboxyglutamate + Vitamin K1 2,3-epoxide + Water → [peptidyl]-glutamate + CO(2) + Oxygen + Phylloquinol	details
Gla protein + Vitamin K1 2,3-epoxide + Water → Gla protein precursor + Phylloquinol + Carbon dioxide + Oxygen	details

Enzyme Details

3. Vitamin K epoxide reductase complex subunit 1

General function:: Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:: Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:: VKORC1
Uniprot ID:: Q9BQB6
Molecular weight:: 18234.3

Reactions

Phylloquinol + Oxidized dithiothreitol → Vitamin K1 2,3-epoxide + 1,4-Dithiothreitol	details

Showing metabocard for Phylloquinol (HMDB0004198)

MOL for HMDB0004198 (Phylloquinol)

3D MOL for HMDB0004198 (Phylloquinol)

3D SDF for HMDB0004198 (Phylloquinol)

3D-SDF for HMDB0004198 (Phylloquinol)

PDB for HMDB0004198 (Phylloquinol)

3D PDB for HMDB0004198 (Phylloquinol)

SMILES for HMDB0004198 (Phylloquinol)

INCHI for HMDB0004198 (Phylloquinol)

Structure for HMDB0004198 (Phylloquinol)

3D Structure for HMDB0004198 (Phylloquinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions