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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:23 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002972

Secondary Accession Numbers

HMDB0062451
HMDB02972
HMDB62451

Metabolite Identification

Common Name

Vitamin K1 2,3-epoxide

Description

Vitamin K1 2,3-epoxide (CAS: 25486-55-9) is a vitamin K derivative. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Within the cell, vitamin K undergoes electron reduction to a reduced form of vitamin K (called vitamin K hydroquinone) by the enzyme vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes vitamin K hydroquinone to allow carboxylation of glutamate into gamma-carboxyglutamate (Gla). This enzyme is called the gamma-glutamyl carboxylase or the vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize vitamin K hydroquinone into vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted into vitamin K by the vitamin K epoxide reductase. These two enzymes comprise the so-called vitamin K cycle. One of the reasons why vitamin K is rarely deficient in a human diet is because vitamin K is continually recycled in our cells. Vitamin K 2,3-epoxide is the substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Significantly increased level of serum vitamin K epoxide has been found in patients with familial multiple coagulation factor deficiency (PMID: 12384421 ). Accumulation of vitamin K1-2,3-epoxide in plasma is also a sensitive marker of the coumarin-like activity of drugs (PMID: 2401753 ).

Structure

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

  Mrv1652305281918102D          

 34 36  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
    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
    2.1375    0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368   -1.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 10  2  0  0  0  0
  3  1  2  0  0  0  0
  3  4  1  0  0  0  0
  4  9  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  2  0  0  0  0
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  7  8  1  0  0  0  0
 11 30  1  0  0  0  0
 30 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 33 34  1  0  0  0  0
 33 32  1  0  0  0  0
 34 31  1  6  0  0  0
 33 31  1  6  0  0  0
  4 34  1  0  0  0  0
 34 11  1  0  0  0  0
  2 33  1  0  0  0  0
M  END

HMDB0002972
     RDKit          3D
Vitamin K1 2,3-epoxide
 80 82  0  0  0  0  0  0  0  0999 V2000
   -2.4441   -0.8456    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.3928   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2617    0.1766    0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2902   -0.3419    1.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4090    0.9478    0.7159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4082    2.0879    1.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311    1.0586   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2160    2.0132   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5212   -0.0570   -1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.7383   -1.3522   -2.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6432   -2.1578   -3.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4269   -0.8676   -1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.5743   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.9725   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    1.0749   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.6064   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771    0.5425   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    1.2619    0.3880 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    1.9536   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    0.6112    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -0.7228    1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4341   -0.2204   -0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3253    2.1642   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8243    2.9926   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    1.4090   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.8603    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8408   -1.1998    1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7337   -3.8473   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -3.1610    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.6484   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629   -1.1484   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.0306   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1176    0.9928   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5258    0.5055    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -1.4886    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6379   -0.9831   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8146    0.5295    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4930    1.8067   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296    1.4221   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417    2.3967    0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6622   -0.9624   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3109    0.2377    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
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  7  5  1  0
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 27 64  1  6
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 30 70  1  0
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 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END

  Mrv1652305281918102D          

 34 36  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
    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
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   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
    2.1375    0.0001    0.0000 O   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  2  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 10  2  0  0  0  0
  3  1  2  0  0  0  0
  3  4  1  0  0  0  0
  4  9  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
 11 30  1  0  0  0  0
 30 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 33 34  1  0  0  0  0
 33 32  1  0  0  0  0
 34 31  1  6  0  0  0
 33 31  1  6  0  0  0
  4 34  1  0  0  0  0
 34 11  1  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002972

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-,30-,31+/m1/s1

> <INCHI_KEY>
KUTXFBIHPWIDJQ-BTPXSFBUSA-N

> <FORMULA>
C31H46O3

> <MOLECULAR_WEIGHT>
466.706

> <EXACT_MASS>
466.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.23339570729761

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

> <ALOGPS_LOGP>
8.28

> <JCHEM_LOGP>
9.222648346666666

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.368148124765553

> <JCHEM_POLAR_SURFACE_AREA>
46.67

> <JCHEM_REFRACTIVITY>
141.68849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphtho[2,3-b]oxirene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002972
     RDKit          3D
Vitamin K1 2,3-epoxide
 80 82  0  0  0  0  0  0  0  0999 V2000
   -2.4441   -0.8456    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.3928   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    0.9639    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533    0.4343    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2617    0.1766    0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2902   -0.3419    1.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4090    0.9478    0.7159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4082    2.0879    1.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311    1.0586   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2160    2.0132   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5212   -0.0570   -1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7066   -0.2924   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7383   -1.3522   -2.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6432   -2.1578   -3.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4581   -1.9372   -2.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4269   -0.8676   -1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.5743   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.9725   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    1.0749   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.6064   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771    0.5425   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    1.2619    0.3880 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    1.9536   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    0.6112    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -0.7228    1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7993   -1.5253    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656   -1.8347   -0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2734   -2.9047   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227   -0.6177   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8692    0.0561   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -0.6581   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1654    0.3088    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4018    1.5376   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4566   -0.4709    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160   -0.7583    1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055   -1.5901    0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -1.3716    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2357    1.9040   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0708    1.2400    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -0.5210    1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0553    1.7927    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4863    2.4161    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8458    2.9776    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5876    0.3360   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6533   -1.5390   -3.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7160   -2.9883   -3.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5792   -2.5454   -2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    1.8736   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.3135   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7290    2.4669    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    2.0983   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    0.2029    0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341   -0.2204   -0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617    2.2006    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    2.1642   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8243    2.9926   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    1.4090   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.8603    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.3172    1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -1.4697    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.8760    2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408   -1.1998    1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7585   -2.5829    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094   -2.2124   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -3.8473   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -3.1610    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.6484   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629   -1.1484   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.0306   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1176    0.9928   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5258    0.5055    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -1.4886    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6379   -0.9831   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8146    0.5295    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4930    1.8067   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296    1.4221   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417    2.3967    0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3843   -1.2685    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6622   -0.9624   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3109    0.2377    0.7764 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
  9 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
 17 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
  7  5  1  0
 16 11  1  0
 17  5  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  1
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  6
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END

HEADER    PROTEIN                                 28-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-19         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  O   UNK     0       1.334   3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.671   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.671   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.338   3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.339   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.673   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.673   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.006   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.990   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.429  -2.106   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
CONECT    1    2    3    6                                                  
CONECT    2    1   10   33                                                  
CONECT    3    1    4    5                                                  
CONECT    4    3    9   34                                                  
CONECT    5    3    7                                                       
CONECT    6    1    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    4                                                            
CONECT   10    2                                                            
CONECT   11   30   34                                                       
CONECT   12   30   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   11   12                                                       
CONECT   31   34   33                                                       
CONECT   32   33                                                            
CONECT   33   34   32   31    2                                             
CONECT   34   33   31    4   11                                             
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

COMPND    HMDB0002972
HETATM    1  C1  UNL     1      -2.444  -0.846   0.659  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.785   0.393  -0.047  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.962   0.964   0.204  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.953   0.434   1.156  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.262   0.177   0.462  1.00  0.00           C  
HETATM    6  O1  UNL     1      -7.290  -0.342   1.343  1.00  0.00           O  
HETATM    7  C6  UNL     1      -7.409   0.948   0.716  1.00  0.00           C  
HETATM    8  C7  UNL     1      -7.408   2.088   1.676  1.00  0.00           C  
HETATM    9  C8  UNL     1      -8.431   1.059  -0.347  1.00  0.00           C  
HETATM   10  O2  UNL     1      -9.216   2.013  -0.496  1.00  0.00           O  
HETATM   11  C9  UNL     1      -8.521  -0.057  -1.307  1.00  0.00           C  
HETATM   12  C10 UNL     1      -9.707  -0.292  -1.983  1.00  0.00           C  
HETATM   13  C11 UNL     1      -9.738  -1.352  -2.880  1.00  0.00           C  
HETATM   14  C12 UNL     1      -8.643  -2.158  -3.108  1.00  0.00           C  
HETATM   15  C13 UNL     1      -7.458  -1.937  -2.440  1.00  0.00           C  
HETATM   16  C14 UNL     1      -7.427  -0.868  -1.536  1.00  0.00           C  
HETATM   17  C15 UNL     1      -6.198  -0.574  -0.791  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.114  -0.972  -1.249  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.938   1.075  -1.043  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.639   1.606  -0.583  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.277   0.543  -0.035  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.578   1.262   0.388  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.260   1.954  -0.728  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.258   0.611   1.492  1.00  0.00           C  
HETATM   25  C22 UNL     1       2.756  -0.723   1.581  1.00  0.00           C  
HETATM   26  C23 UNL     1       3.799  -1.525   1.045  1.00  0.00           C  
HETATM   27  C24 UNL     1       4.166  -1.835  -0.335  1.00  0.00           C  
HETATM   28  C25 UNL     1       5.273  -2.905  -0.398  1.00  0.00           C  
HETATM   29  C26 UNL     1       4.723  -0.618  -1.084  1.00  0.00           C  
HETATM   30  C27 UNL     1       5.869   0.056  -0.451  1.00  0.00           C  
HETATM   31  C28 UNL     1       7.152  -0.658  -0.260  1.00  0.00           C  
HETATM   32  C29 UNL     1       8.165   0.309   0.418  1.00  0.00           C  
HETATM   33  C30 UNL     1       8.402   1.538  -0.418  1.00  0.00           C  
HETATM   34  C31 UNL     1       9.457  -0.471   0.570  1.00  0.00           C  
HETATM   35  H1  UNL     1      -2.116  -0.758   1.693  1.00  0.00           H  
HETATM   36  H2  UNL     1      -3.306  -1.590   0.659  1.00  0.00           H  
HETATM   37  H3  UNL     1      -1.619  -1.372   0.088  1.00  0.00           H  
HETATM   38  H4  UNL     1      -4.236   1.904  -0.319  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.071   1.240   1.939  1.00  0.00           H  
HETATM   40  H6  UNL     1      -4.661  -0.521   1.639  1.00  0.00           H  
HETATM   41  H7  UNL     1      -7.055   1.793   2.682  1.00  0.00           H  
HETATM   42  H8  UNL     1      -8.486   2.416   1.823  1.00  0.00           H  
HETATM   43  H9  UNL     1      -6.846   2.978   1.296  1.00  0.00           H  
HETATM   44  H10 UNL     1     -10.588   0.336  -1.814  1.00  0.00           H  
HETATM   45  H11 UNL     1     -10.653  -1.539  -3.409  1.00  0.00           H  
HETATM   46  H12 UNL     1      -8.716  -2.988  -3.835  1.00  0.00           H  
HETATM   47  H13 UNL     1      -6.579  -2.545  -2.584  1.00  0.00           H  
HETATM   48  H14 UNL     1      -2.510   1.874  -1.574  1.00  0.00           H  
HETATM   49  H15 UNL     1      -1.746   0.314  -1.835  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.729   2.467   0.134  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.147   2.098  -1.481  1.00  0.00           H  
HETATM   52  H18 UNL     1      -0.143   0.203   0.933  1.00  0.00           H  
HETATM   53  H19 UNL     1       0.434  -0.220  -0.784  1.00  0.00           H  
HETATM   54  H20 UNL     1       1.062   2.201   0.945  1.00  0.00           H  
HETATM   55  H21 UNL     1       3.325   2.164  -0.460  1.00  0.00           H  
HETATM   56  H22 UNL     1       1.824   2.993  -0.966  1.00  0.00           H  
HETATM   57  H23 UNL     1       2.149   1.409  -1.706  1.00  0.00           H  
HETATM   58  H24 UNL     1       1.619   0.860   2.461  1.00  0.00           H  
HETATM   59  H25 UNL     1       3.151   1.317   1.756  1.00  0.00           H  
HETATM   60  H26 UNL     1       1.809  -1.470   1.557  1.00  0.00           H  
HETATM   61  H27 UNL     1       2.888  -0.876   2.781  1.00  0.00           H  
HETATM   62  H28 UNL     1       4.841  -1.200   1.551  1.00  0.00           H  
HETATM   63  H29 UNL     1       3.759  -2.583   1.583  1.00  0.00           H  
HETATM   64  H30 UNL     1       3.309  -2.212  -0.950  1.00  0.00           H  
HETATM   65  H31 UNL     1       4.734  -3.847  -0.770  1.00  0.00           H  
HETATM   66  H32 UNL     1       5.604  -3.161   0.620  1.00  0.00           H  
HETATM   67  H33 UNL     1       6.000  -2.648  -1.157  1.00  0.00           H  
HETATM   68  H34 UNL     1       5.163  -1.148  -2.034  1.00  0.00           H  
HETATM   69  H35 UNL     1       3.924   0.031  -1.424  1.00  0.00           H  
HETATM   70  H36 UNL     1       6.118   0.993  -1.068  1.00  0.00           H  
HETATM   71  H37 UNL     1       5.526   0.506   0.542  1.00  0.00           H  
HETATM   72  H38 UNL     1       7.103  -1.489   0.463  1.00  0.00           H  
HETATM   73  H39 UNL     1       7.638  -0.983  -1.206  1.00  0.00           H  
HETATM   74  H40 UNL     1       7.815   0.530   1.442  1.00  0.00           H  
HETATM   75  H41 UNL     1       9.493   1.807  -0.311  1.00  0.00           H  
HETATM   76  H42 UNL     1       8.130   1.422  -1.474  1.00  0.00           H  
HETATM   77  H43 UNL     1       7.842   2.397   0.005  1.00  0.00           H  
HETATM   78  H44 UNL     1       9.384  -1.269   1.342  1.00  0.00           H  
HETATM   79  H45 UNL     1       9.662  -0.962  -0.411  1.00  0.00           H  
HETATM   80  H46 UNL     1      10.311   0.238   0.776  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   19
CONECT    3    4   38
CONECT    4    5   39   40
CONECT    5    6    7   17
CONECT    6    7
CONECT    7    8    9
CONECT    8   41   42   43
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   44
CONECT   13   14   14   45
CONECT   14   15   46
CONECT   15   16   16   47
CONECT   16   17
CONECT   17   18   18
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   24   54
CONECT   23   55   56   57
CONECT   24   25   58   59
CONECT   25   26   60   61
CONECT   26   27   62   63
CONECT   27   28   29   64
CONECT   28   65   66   67
CONECT   29   30   68   69
CONECT   30   31   70   71
CONECT   31   32   72   73
CONECT   32   33   34   74
CONECT   33   75   76   77
CONECT   34   78   79   80
END

HMDB0002972
     RDKit          3D
Vitamin K1 2,3-epoxide
 80 82  0  0  0  0  0  0  0  0999 V2000
   -2.4441   -0.8456    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.3928   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    0.9639    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533    0.4343    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2617    0.1766    0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2902   -0.3419    1.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4090    0.9478    0.7159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4082    2.0879    1.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311    1.0586   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2160    2.0132   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5212   -0.0570   -1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7066   -0.2924   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7383   -1.3522   -2.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6432   -2.1578   -3.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4581   -1.9372   -2.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4269   -0.8676   -1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.5743   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.9725   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    1.0749   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.6064   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771    0.5425   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    1.2619    0.3880 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    1.9536   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    0.6112    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -0.7228    1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7993   -1.5253    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656   -1.8347   -0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2734   -2.9047   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227   -0.6177   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8692    0.0561   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -0.6581   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1654    0.3088    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4018    1.5376   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4566   -0.4709    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160   -0.7583    1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055   -1.5901    0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191   -1.3716    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2357    1.9040   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0708    1.2400    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -0.5210    1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0553    1.7927    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4863    2.4161    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8458    2.9776    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5876    0.3360   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6533   -1.5390   -3.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7160   -2.9883   -3.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5792   -2.5454   -2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    1.8736   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.3135   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7290    2.4669    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    2.0983   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    0.2029    0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341   -0.2204   -0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617    2.2006    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    2.1642   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8243    2.9926   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    1.4090   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.8603    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.3172    1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -1.4697    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.8760    2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408   -1.1998    1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7585   -2.5829    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094   -2.2124   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -3.8473   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -3.1610    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.6484   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629   -1.1484   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.0306   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1176    0.9928   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5258    0.5055    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1030   -1.4886    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6379   -0.9831   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8146    0.5295    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4930    1.8067   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296    1.4221   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417    2.3967    0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3843   -1.2685    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6622   -0.9624   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3109    0.2377    0.7764 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
  9 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
 17 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
  7  5  1  0
 16 11  1  0
 17  5  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  1
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  6
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2,3-Epoxyphytyl)menaquinone	HMDB
2,3-Epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone	HMDB
2,3-Epoxyphylloquinone	HMDB
1a,7a-Dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dione	HMDB
Phylloquinone oxide	HMDB
Phylloquinone epoxide	HMDB
Phylloquinone-2,3-epoxide	HMDB
Vitamin K1 oxide	HMDB
Vitamin K epoxide	HMDB
Vitamin K(1) oxide	HMDB
Vitamin K1 epoxide	HMDB
1,4-Naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinone	HMDB
Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxide	HMDB
Phylloquinone, epoxide	HMDB
Vitamin K 2,3-epoxide	HMDB
Vitamin K1, epoxide	HMDB
Phylloquinone 2,3-epoxide	HMDB
Vitamin K oxide	HMDB
Vitamin K1 2,3-epoxide	HMDB

Chemical Formula

C₃₁H₄₆O₃

Average Molecular Weight

466.706

Monoisotopic Molecular Weight

466.344695341

IUPAC Name

(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

Traditional Name

(1aS,7aR)-1a-methyl-7a-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphtho[2,3-b]oxirene-2,7-dione

CAS Registry Number

85955-78-8

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=O

InChI Identifier

InChI=1S/C31H46O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-,30-,31+/m1/s1

InChI Key

KUTXFBIHPWIDJQ-BTPXSFBUSA-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
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
Benzenoid
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2851012)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002972)

Source

Endogenous

Endogenous (HMDB: HMDB0002972)

Animal

Animal (HMDB: HMDB0002972)

Exogenous

Food

Food (HMDB: HMDB0002972)

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)

Exogenous (HMDB: HMDB0002972)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002972)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002972)
Vitamin K Metabolism (PathBank: SMP0063591)

Lipid metabolism pathway (HMDB: HMDB0002972)

Drug action pathway

Enoxaparin Action Pathway (PathBank: SMP0000272)
Fondaparinux Action Pathway (PathBank: SMP0000273)
Heparin Action Pathway (PathBank: SMP0000274)
Ardeparin Action Pathway (PathBank: SMP0000275)
Argatroban Action Pathway (PathBank: SMP0000276)
Bivalirudin Action Pathway (PathBank: SMP0000277)
Lepirudin Action Pathway (PathBank: SMP0000278)
Ximelagatran Action Pathway (PathBank: SMP0000279)
Alteplase Action Pathway (PathBank: SMP0000280)
Anistreplase Action Pathway (PathBank: SMP0000281)
Streptokinase Action Pathway (PathBank: SMP0000282)
Tenecteplase Action Pathway (PathBank: SMP0000283)
Urokinase Action Pathway (PathBank: SMP0000284)
Reteplase Action Pathway (PathBank: SMP0000285)
Aminocaproic Acid Action Pathway (PathBank: SMP0000286)
Tranexamic Acid Action Pathway (PathBank: SMP0000287)
Aprotinin Action Pathway (PathBank: SMP0000288)
Warfarin Action Pathway (PathBank: SMP0000268)
Acenocoumarol Action Pathway (PathBank: SMP0000269)
Dicumarol Action Pathway (PathBank: SMP0000270)
Phenprocoumon Action Pathway (PathBank: SMP0000271)
Phenindione Action Pathway (PathBank: SMP0000655)
Dicoumarol Action Pathway (PathBank: SMP0000656)

Cellular process

Cell signaling (HMDB: HMDB0002972)

Biochemical process

Lipid transport (HMDB: HMDB0002972)

Multicellular process

Coagulation (PathBank: SMP0119368)

Role

Biological role

Energy source (HMDB: HMDB0002972)

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	2.2e-05 g/L	ALOGPS
logP	8.28	ALOGPS
logP	9.22	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.67 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	141.69 m³·mol⁻¹	ChemAxon
Polarizability	56.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	250.55	30932474
DeepCCS	[M+Na]+	226.461	30932474
AllCCS	[M+H]+	221.3	32859911
AllCCS	[M+H-H2O]+	219.6	32859911
AllCCS	[M+NH4]+	222.9	32859911
AllCCS	[M+Na]+	223.4	32859911
AllCCS	[M-H]-	218.0	32859911
AllCCS	[M+Na-2H]-	221.0	32859911
AllCCS	[M+HCOO]-	224.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vitamin K1 2,3-epoxide	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=O	4192.2	Standard polar	33892256
Vitamin K1 2,3-epoxide	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=O	3284.5	Standard non polar	33892256
Vitamin K1 2,3-epoxide	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=O	3350.3	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 - Vitamin K1 2,3-epoxide 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 - Vitamin K1 2,3-epoxide 10V, Negative-QTOF	splash10-014i-0000900000-34d4a26fdf7a1cd26730	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 20V, Negative-QTOF	splash10-014r-0200900000-9ed845fe28276c1a2640	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 40V, Negative-QTOF	splash10-004r-0209100000-2b233ea9a16eecb88522	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 10V, Positive-QTOF	splash10-014i-0012900000-5563789bc0b75fbe920c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 20V, Positive-QTOF	splash10-0a4j-9730300000-4af0219041341f3904b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin K1 2,3-epoxide 40V, Positive-QTOF	splash10-0002-9711000000-82abc89ed052cf2ea570	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0000021 uM	Adult (>18 years old)	Both	Normal	2851012	details

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

FDB023087

KNApSAcK ID

Not Available

Chemspider ID

34993195

KEGG Compound ID

C05849

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3030

PubChem Compound

90479364

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Komatsu K, Kayashima N, Ariyoshi N, Shirahata A: [Vitamin K]. Nihon Rinsho. 1993 Apr;51(4):943-51. [PubMed:8483276 ]
Hirauchi K, Sakano T, Nagaoka T, Morimoto A: Simultaneous determination of vitamin K1, vitamin K1 2,3-epoxide and menaquinone-4 in human plasma by high-performance liquid chromatography with fluorimetric detection. J Chromatogr. 1988 Aug 19;430(1):21-9. [PubMed:2851012 ]
McBurney A, Shearer MJ, Barkhan P: Changes in the urinary metabolites of phylloquinone (vitamin K1) in man following therapeutic anticoagulation with warfarin. Biochem Pharmacol. 1978 Feb 1;27(3):273-8. [PubMed:619911 ]
Fregin A, Rost S, Wolz W, Krebsova A, Muller CR, Oldenburg J: Homozygosity mapping of a second gene locus for hereditary combined deficiency of vitamin K-dependent clotting factors to the centromeric region of chromosome 16. Blood. 2002 Nov 1;100(9):3229-32. [PubMed:12384421 ]
Trenk D, Wagner F, Bechtold H, Nies B, Jahnchen E: Lack of effect of cefixime on the metabolism of vitamin K1. J Clin Pharmacol. 1990 Aug;30(8):737-42. [PubMed:2401753 ]

Enzymes

Enzyme Details

1. 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

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

Showing metabocard for Vitamin K1 2,3-epoxide (HMDB0002972)

MOL for HMDB0002972 (Vitamin K1 2,3-epoxide)

3D MOL for HMDB0002972 (Vitamin K1 2,3-epoxide)

3D SDF for HMDB0002972 (Vitamin K1 2,3-epoxide)

3D-SDF for HMDB0002972 (Vitamin K1 2,3-epoxide)

PDB for HMDB0002972 (Vitamin K1 2,3-epoxide)

3D PDB for HMDB0002972 (Vitamin K1 2,3-epoxide)

SMILES for HMDB0002972 (Vitamin K1 2,3-epoxide)

INCHI for HMDB0002972 (Vitamin K1 2,3-epoxide)

Structure for HMDB0002972 (Vitamin K1 2,3-epoxide)

3D Structure for HMDB0002972 (Vitamin K1 2,3-epoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions