NP-MRD: Showing NP-Card for 2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione (NP0192029)

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Record Information

Version

2.0

Created at

2022-09-04 09:08:51 UTC

Updated at

2022-09-04 09:08:51 UTC

NP-MRD ID

NP0192029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione

Description

Menaquinone-9, also known as MK-9, 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. Thus, menaquinone-9 is considered to be a quinone lipid molecule. 2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione is found in Alicyclobacillus acidocaldarius, Streptomyces indicus, Streptomyces otsuchiensis and Streptomyces roseicoloratus. 2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione was first documented in 1992 (PMID: 1542008). Menaquinone-9 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12054615) (PMID: 1552370) (PMID: 7601837) (PMID: 7638250).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08091208242D          

 66 67  0  0  0  0            999 V2000
   16.4328   24.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   23.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   20.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   18.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   15.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   13.2000    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
   15.7184   22.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8605   18.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4315   15.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5737   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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   16.4328   23.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   21.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   13.6125    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
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    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0  0  0  0
 22 14  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
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 26 16  1  0  0  0  0
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 28 17  1  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 18  1  0  0  0  0
 32 19  1  0  0  0  0
 33 19  1  0  0  0  0
 34 20  1  0  0  0  0
 35 20  1  0  0  0  0
 36 21  1  0  0  0  0
 37 21  1  0  0  0  0
 38 12  1  0  0  0  0
 39 13  1  0  0  0  0
 41 40  1  0  0  0  0
 42  1  1  0  0  0  0
 42  2  1  0  0  0  0
 42 22  2  0  0  0  0
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 43 23  1  0  0  0  0
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 59 24  1  0  0  0  0
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 63 32  1  0  0  0  0
 64 34  1  0  0  0  0
 65 36  1  0  0  0  0
 66 40  1  0  0  0  0
M  END

     RDKit          3D

138139  0  0  0  0  0  0  0  0999 V2000
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  -16.5890    2.7201    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 08091208242D          

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M  END
> <DATABASE_ID>
NP0192029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])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/C56H80O2/c1-42(2)22-14-23-43(3)24-15-25-44(4)26-16-27-45(5)28-17-29-46(6)30-18-31-47(7)32-19-33-48(8)34-20-35-49(9)36-21-37-50(10)40-41-52-51(11)55(57)53-38-12-13-39-54(53)56(52)58/h12-13,22,24,26,28,30,32,34,36,38-40H,14-21,23,25,27,29,31,33,35,37,41H2,1-11H3/b43-24+,44-26+,45-28+,46-30+,47-32+,48-34+,49-36+,50-40+

> <INCHI_KEY>
WCRXHNIUHQUASO-UVZVDVBNSA-N

> <FORMULA>
C56H80O2

> <MOLECULAR_WEIGHT>
785.2332

> <EXACT_MASS>
784.615831804

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
102.14611828729178

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
10.23

> <JCHEM_LOGP>
16.778278739333334

> <ALOGPS_LOGS>
-6.62

> <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>
264.5198

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-AUG-12         0                                  
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HETATM   41  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   42                                                            
CONECT    2   42                                                            
CONECT    3   43                                                            
CONECT    4   44                                                            
CONECT    5   45                                                            
CONECT    6   46                                                            
CONECT    7   47                                                            
CONECT    8   48                                                            
CONECT    9   49                                                            
CONECT   10   50                                                            
CONECT   11   51                                                            
CONECT   12   13   38                                                       
CONECT   13   12   39                                                       
CONECT   14   22   23                                                       
CONECT   15   24   25                                                       
CONECT   16   26   27                                                       
CONECT   17   28   29                                                       
CONECT   18   30   31                                                       
CONECT   19   32   33                                                       
CONECT   20   34   35                                                       
CONECT   21   36   37                                                       
CONECT   22   14   42                                                       
CONECT   23   14   43                                                       
CONECT   24   15   43   59                                                  
CONECT   25   15   44                                                       
CONECT   26   16   44   60                                                  
CONECT   27   16   45                                                       
CONECT   28   17   45   61                                                  
CONECT   29   17   46                                                       
CONECT   30   18   46   62                                                  
CONECT   31   18   47                                                       
CONECT   32   19   47   63                                                  
CONECT   33   19   48                                                       
CONECT   34   20   48   64                                                  
CONECT   35   20   49                                                       
CONECT   36   21   49   65                                                  
CONECT   37   21   50                                                       
CONECT   38   12   53                                                       
CONECT   39   13   54                                                       
CONECT   40   41   50   66                                                  
CONECT   41   40   52                                                       
CONECT   42    1    2   22                                                  
CONECT   43    3   23   24                                                  
CONECT   44    4   25   26                                                  
CONECT   45    5   27   28                                                  
CONECT   46    6   29   30                                                  
CONECT   47    7   31   32                                                  
CONECT   48    8   33   34                                                  
CONECT   49    9   35   36                                                  
CONECT   50   10   37   40                                                  
CONECT   51   11   52   55                                                  
CONECT   52   41   51   56                                                  
CONECT   53   38   54   55                                                  
CONECT   54   39   53   56                                                  
CONECT   55   51   53   57                                                  
CONECT   56   52   54   58                                                  
CONECT   57   55                                                            
CONECT   58   56                                                            
CONECT   59   24                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   30                                                            
CONECT   63   32                                                            
CONECT   64   34                                                            
CONECT   65   36                                                            
CONECT   66   40                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  134    0
END

View in JSmol

Synonyms

Value	Source
Menaquinone 9	ChEBI
Menaquinone with nine isoprene units	ChEBI
MK-9	ChEBI
MK9	ChEBI

Chemical Formula

C₅₆H₈₀O₂

Average Mass

785.2332 Da

Monoisotopic Mass

784.61583 Da

IUPAC Name

2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]-1,4-dihydronaphthalene-1,4-dione

Traditional Name

2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])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/C56H80O2/c1-42(2)22-14-23-43(3)24-15-25-44(4)26-16-27-45(5)28-17-29-46(6)30-18-31-47(7)32-19-33-48(8)34-20-35-49(9)36-21-37-50(10)40-41-52-51(11)55(57)53-38-12-13-39-54(53)56(52)58/h12-13,22,24,26,28,30,32,34,36,38-40H,14-21,23,25,27,29,31,33,35,37,41H2,1-11H3/b43-24+,44-26+,45-28+,46-30+,47-32+,48-34+,49-36+,50-40+

InChI Key

WCRXHNIUHQUASO-UVZVDVBNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alicyclobacillus acidocaldarius	LOTUS Database	35616633
Streptomyces indicus	LOTUS Database	35616633
Streptomyces otsuchiensis	LOTUS Database	35616633
Streptomyces roseicoloratus	LOTUS Database	35616633

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

Polyterpenoid
Menaquinone
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

Ubiquinones (LMPR02010041 )

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	10.23	ALOGPS
logP	16.78	ChemAxon
logS	-6.6	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	26	ChemAxon
Refractivity	264.52 m³·mol⁻¹	ChemAxon
Polarizability	102.15 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-9720

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6289935

PDB ID

Not Available

ChEBI ID

44147

Good Scents ID

Not Available

References

General References

Das SK, Chatterjee D, Uddin M: Induction of pro-renin converting enzyme mk9 by thyroid hormone in the guinea-pig liver. Biochem Biophys Res Commun. 2002 Apr 26;293(1):412-5. doi: 10.1016/S0006-291X(02)00250-4. [PubMed:12054615 ]
Ichihashi T, Takagishi Y, Uchida K, Yamada H: Colonic absorption of menaquinone-4 and menaquinone-9 in rats. J Nutr. 1992 Mar;122(3):506-12. doi: 10.1093/jn/122.3.506. [PubMed:1542008 ]
Will BH, Suttie JW: Comparative metabolism of phylloquinone and menaquinone-9 in rat liver. J Nutr. 1992 Apr;122(4):953-8. doi: 10.1093/jn/122.4.953. [PubMed:1552370 ]
Brito F, DeMoss JA, Dubourdieu M: Isolation and identification of menaquinone-9 from purified nitrate reductase of Escherichia coli. J Bacteriol. 1995 Jul;177(13):3728-35. doi: 10.1128/jb.177.13.3728-3735.1995. [PubMed:7601837 ]
Reedstrom CK, Suttie JW: Comparative distribution, metabolism, and utilization of phylloquinone and menaquinone-9 in rat liver. Proc Soc Exp Biol Med. 1995 Sep;209(4):403-9. doi: 10.3181/00379727-209-43915. [PubMed:7638250 ]
LOTUS database [Link]

Showing NP-Card for 2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione (NP0192029)

MOL for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

3D MOL for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

3D SDF for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

3D-SDF for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

PDB for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

3D PDB for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

SMILES for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

INCHI for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

Structure for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)

3D Structure for NP0192029 (2-methyl-3-[(2e,6e,10e,14e,18e,22e,26e,30e)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]naphthalene-1,4-dione)