NP-MRD: Showing NP-Card for Menatetrenone (NP0049975)

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Record Information

Version

2.0

Created at

2022-03-17 21:21:10 UTC

Updated at

2024-09-03 04:17:42 UTC

NP-MRD ID

NP0049975

Natural Product DOI

https://doi.org/10.57994/1137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Menatetrenone

Description

Menatetrenone, also known as menaquinone 4 or vitamin K2, belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group. Menatetrenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Menatetrenone exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Menatetrenone is found, on average, in the highest concentration within a few different foods, such as sausages, cold cuts, and eggs and in a lower concentration in pink salmons, empanada, and macaroni and cheeses. Menatetrenone has also been detected, but not quantified in, several different foods, such as common pea, other soy products, feijoa, alaska pollocks, and enokitakes. This could make menatetrenone a potential biomarker for the consumption of these foods. Menatetrenone was first documented in 2013 (PMID: 22692649). Menatetrenone has been used in trials studying the treatment of Diabetes, Osteoporosis, Prediabetic State, and Hepatocellular Carcinoma (PMID: 23169578) (PMID: 23346882) (PMID: 23702931) (PMID: 23832575) (PMID: 24085302) (PMID: 24138531).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306301800182D          

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


  Mrv1652306301800182D          

 36 37  0  0  0  0            999 V2000
    9.2881   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18  7  1  0  0  0  0
 19  8  1  0  0  0  0
 21 20  1  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  2  0  0  0  0
 23  3  1  0  0  0  0
 23 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24  4  1  0  0  0  0
 24 15  1  0  0  0  0
 24 16  2  0  0  0  0
 25  5  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  2  0  0  0  0
 26  6  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  2  0  0  0  0
 28 18  2  0  0  0  0
 29 19  2  0  0  0  0
 29 28  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  2  0  0  0  0
 33 31  2  0  0  0  0
 34 14  1  0  0  0  0
 35 16  1  0  0  0  0
 36 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049975

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

> <INCHI_KEY>
DKHGMERMDICWDU-GHDNBGIDSA-N

> <FORMULA>
C31H40O2

> <MOLECULAR_WEIGHT>
444.659

> <EXACT_MASS>
444.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.9249299778513

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
8.479707364333333

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.224343414413889

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
145.50680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
menatetrenone

> <JCHEM_VEBER_RULE>
0

$$$$

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

View in JSmol

Synonyms

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

Chemical Formula

C₃₁H₄₀O₂

Average Mass

444.6590 Da

Monoisotopic Mass

444.30283 Da

IUPAC Name

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

Traditional Name

menatetrenone

CAS Registry Number

863-61-6

SMILES

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

InChI Identifier

InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

InChI Key

DKHGMERMDICWDU-GHDNBGIDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amaranthus	FooDB	USDA
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	USDA
Bos taurus X Bison bison	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	USDA
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Caridea	FooDB	USDA
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chenopodium album	FooDB	USDA
Chenopodium quinoa	FooDB	USDA
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Coregonus	FooDB	USDA
Crassostrea virginica	FooDB	USDA
Cucurbita maxima	FooDB	USDA
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	USDA
Eutrema japonicum	FooDB	USDA
Feijoa sellowiana	FooDB	USDA
Gadiformes	FooDB	USDA
Gadus macrocephalus	FooDB	USDA
Gallus gallus	FooDB	FooDB
Glycine max	FooDB	USDA
Grifola frondosa	FooDB	USDA
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	USDA
Hippoglossus stenolepis	FooDB	USDA
Homarus americanus	FooDB	USDA
Ictalurus punctatus	FooDB	USDA
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Linum usitatissimum	FooDB	USDA
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Microstomus kitt	FooDB	USDA
Nephropidae	FooDB	USDA
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Olea europaea	FooDB	USDA
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus keta	FooDB	USDA
Oncorhynchus mykiss	FooDB	USDA
Oncorhynchus nerka	FooDB	USDA
Oncorhynchus tshawytscha	FooDB	USDA
Opuntia macrorhiza	FooDB	USDA
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	USDA
Osmeridae	FooDB	USDA
Ovis aries	FooDB	FooDB
Panicum miliaceum	FooDB	USDA
Pectinidae	FooDB	USDA
Pediomelum esculentum	FooDB	USDA
Phaseolus vulgaris	FooDB	USDA
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pleuronectiformes	FooDB	USDA
Pleurotus ostreatus	FooDB	USDA
Pollachius	FooDB	USDA
Prunus domestica	FooDB	USDA
Prunus dulcis	FooDB	USDA
Prunus virginiana	FooDB	USDA
Rosa	FooDB	USDA
Rubus spectabilis	FooDB	USDA
Salmo salar	FooDB	USDA
Sebastes	FooDB	USDA
Sebastes alutus	FooDB	USDA
Siluriformes	FooDB	USDA
Solanum lycopersicum	FooDB	USDA
Solanum lycopersicum var. lycopersicum	FooDB	USDA
Solanum tuberosum	FooDB	USDA
Soleidae	FooDB	USDA
Sorghum bicolor	FooDB	USDA
Stenodus leucichthys	FooDB	USDA
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	USDA
Triticum spelta	FooDB	USDA
Triticum turanicum	FooDB	USDA
Typha angustifolia	FooDB	USDA
Vaccinium ovalifolium	FooDB	USDA
Zea mays L.	FooDB	USDA

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Menaquinones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

menaquinone (CHEBI:78277 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

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

External Links

HMDB ID

HMDB0030017

DrugBank ID

DB12148

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029792

KNApSAcK ID

Not Available

Chemspider ID

4445530

KEGG Compound ID

C00828

BioCyc ID

CPD-9726

BiGG ID

Not Available

Wikipedia Link

Menatetrenone

METLIN ID

Not Available

PubChem Compound

5282367

PDB ID

Not Available

ChEBI ID

78277

Good Scents ID

Not Available

References

General References

Suzuki K, Tsuji S, Fukushima Y, Nakase T, Hamada M, Tomita T, Yoshikawa H: Clinical results of alendronate monotherapy and combined therapy with menatetrenone (VitK(2)) in postmenopausal RA patients. Mod Rheumatol. 2013 May;23(3):450-5. doi: 10.1007/s10165-012-0678-x. Epub 2012 Jun 13. [PubMed:22692649 ]
Nickerson ML, Bosley AD, Weiss JS, Kostiha BN, Hirota Y, Brandt W, Esposito D, Kinoshita S, Wessjohann L, Morham SG, Andresson T, Kruth HS, Okano T, Dean M: The UBIAD1 prenyltransferase links menaquinone-4 [corrected] synthesis to cholesterol metabolic enzymes. Hum Mutat. 2013 Feb;34(2):317-29. doi: 10.1002/humu.22230. Epub 2012 Nov 27. [PubMed:23169578 ]
Iwamoto J, Sato Y: Menatetrenone for the treatment of osteoporosis. Expert Opin Pharmacother. 2013 Mar;14(4):449-58. doi: 10.1517/14656566.2013.763796. Epub 2013 Jan 25. [PubMed:23346882 ]
Koitaya N, Sekiguchi M, Tousen Y, Nishide Y, Morita A, Yamauchi J, Gando Y, Miyachi M, Aoki M, Komatsu M, Watanabe F, Morishita K, Ishimi Y: Low-dose vitamin K2 (MK-4) supplementation for 12 months improves bone metabolism and prevents forearm bone loss in postmenopausal Japanese women. J Bone Miner Metab. 2014 Mar;32(2):142-50. doi: 10.1007/s00774-013-0472-7. Epub 2013 May 24. [PubMed:23702931 ]
Inoue K, Hamano T, Nango N, Matsui I, Tomida K, Mikami S, Fujii N, Nakano C, Obi Y, Shimomura A, Kusunoki Y, Rakugi H, Isaka Y, Tsubakihara Y: Multidetector-row computed tomography is useful to evaluate the therapeutic effects of bisphosphonates in glucocorticoid-induced osteoporosis. J Bone Miner Metab. 2014 May;32(3):271-80. doi: 10.1007/s00774-013-0485-2. Epub 2013 Jul 6. [PubMed:23832575 ]
Hirota Y, Tsugawa N, Nakagawa K, Suhara Y, Tanaka K, Uchino Y, Takeuchi A, Sawada N, Kamao M, Wada A, Okitsu T, Okano T: Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats. J Biol Chem. 2013 Nov 15;288(46):33071-80. doi: 10.1074/jbc.M113.477356. Epub 2013 Sep 30. [PubMed:24085302 ]
Edson KZ, Prasad B, Unadkat JD, Suhara Y, Okano T, Guengerich FP, Rettie AE: Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry. 2013 Nov 19;52(46):8276-85. doi: 10.1021/bi401208m. Epub 2013 Nov 7. [PubMed:24138531 ]
Guralp O, Erel CT: Effects of vitamin K in postmenopausal women: mini review. Maturitas. 2014 Mar;77(3):294-9. doi: 10.1016/j.maturitas.2013.11.002. Epub 2013 Nov 27. [PubMed:24342502 ]
Jiang Y, Zhang ZL, Zhang ZL, Zhu HM, Wu YY, Cheng Q, Wu FL, Xing XP, Liu JL, Yu W, Meng XW: Menatetrenone versus alfacalcidol in the treatment of Chinese postmenopausal women with osteoporosis: a multicenter, randomized, double-blinded, double-dummy, positive drug-controlled clinical trial. Clin Interv Aging. 2014;9:121-7. doi: 10.2147/CIA.S54107. Epub 2014 Jan 8. [PubMed:24426779 ]
Shearer MJ, Newman P: Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. J Lipid Res. 2014 Mar;55(3):345-62. doi: 10.1194/jlr.R045559. Epub 2014 Jan 31. [PubMed:24489112 ]
Rodbotten R, Gundersen T, Vermeer C, Kirkhus B: Vitamin K2 in different bovine muscles and breeds. Meat Sci. 2014 May;97(1):49-53. doi: 10.1016/j.meatsci.2014.01.005. Epub 2014 Jan 22. [PubMed:24508562 ]
Gentili A, Cafolla A, Gasperi T, Bellante S, Caretti F, Curini R, Fernandez VP: Rapid, high performance method for the determination of vitamin K(1), menaquinone-4 and vitamin K(1) 2,3-epoxide in human serum and plasma using liquid chromatography-hybrid quadrupole linear ion trap mass spectrometry. J Chromatogr A. 2014 Apr 18;1338:102-10. doi: 10.1016/j.chroma.2014.02.065. Epub 2014 Feb 28. [PubMed:24630057 ]
Hanzawa F, Sakuma E, Nomura S, Uchida T, Oda H, Ikeda S: Excess alpha-tocopherol decreases extrahepatic phylloquinone in phylloquinone-fed rats but not menaquinone-4 in menaquinone-4-fed rats. Mol Nutr Food Res. 2014 Aug;58(8):1601-9. doi: 10.1002/mnfr.201300710. Epub 2014 Apr 16. [PubMed:24737747 ]
Iwamoto J: Vitamin K(2) therapy for postmenopausal osteoporosis. Nutrients. 2014 May 16;6(5):1971-80. doi: 10.3390/nu6051971. [PubMed:24841104 ]
Iwamoto J, Sato Y, Matsumoto H: Vitamin K2 improves femoral bone strength without altering bone mineral density in gastrectomized rats. J Nutr Sci Vitaminol (Tokyo). 2014;60(2):71-7. doi: 10.3177/jnsv.60.71. [PubMed:24975215 ]

Showing NP-Card for Menatetrenone (NP0049975)

MOL for NP0049975 (Menatetrenone)

3D MOL for NP0049975 (Menatetrenone)

3D SDF for NP0049975 (Menatetrenone)

3D-SDF for NP0049975 (Menatetrenone)

PDB for NP0049975 (Menatetrenone)

3D PDB for NP0049975 (Menatetrenone)

SMILES for NP0049975 (Menatetrenone)

INCHI for NP0049975 (Menatetrenone)

Structure for NP0049975 (Menatetrenone)

3D Structure for NP0049975 (Menatetrenone)