NP-MRD: Showing NP-Card for alpha-Tocopherolquinone (NP0047963)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:48 UTC

Updated at

2022-03-17 20:48:48 UTC

NP-MRD ID

NP0047963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Tocopherolquinone

Description

Alpha-Tocopherolquinone, also known as D 178 or eutrophyl, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Alpha-Tocopherolquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, alpha-Tocopherolquinone has been detected, but not quantified in, several different foods, such as anises, barley, brassicas, and spinachs. alpha-Tocopherolquinone is found in Beilschmiedia erythrophloia, Beilschmiedia tsangii, Bidens pilosa, Caulerpa racemosa, Cryptocarya chinensis, Fatoua villosa, Garcinia multiflora, Gentiana lutea , Hellenia speciosa, Ixora coccinea, Himalaiella deltoidea, Litsea acutivena, Muntingia calabura, Myriactis humilis, Nepeta tuberosa, Parentucellia latifolia, Photinia lucida, Selaginella delicatula, Spinacia oleracea , Swertia angustifolia, Synsepalum dulcificum, Vitex negundo and Zanthoxylum beecheyanum. This could make alpha-tocopherolquinone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307472D          

 32 32  0  0  0  0            999 V2000
   10.0026    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8782    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7032    1.3480    0.0000 O   0  0  0  0  0  0  0  0  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
 18 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20 12  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  4  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  0  0  0  0
 24 23  2  0  0  0  0
 25  7  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  2  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29  8  1  0  0  0  0
 29 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 27  2  0  0  0  0
 31 28  2  0  0  0  0
 32 29  1  0  0  0  0
M  END


  Mrv0541 05061307472D          

 32 32  0  0  0  0            999 V2000
   10.0026    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8782    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7032    1.3480    0.0000 O   0  0  0  0  0  0  0  0  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
 18 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20 12  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  4  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23  5  1  0  0  0  0
 24  6  1  0  0  0  0
 24 23  2  0  0  0  0
 25  7  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  2  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29  8  1  0  0  0  0
 29 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 27  2  0  0  0  0
 31 28  2  0  0  0  0
 32 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3

> <INCHI_KEY>
LTVDFSLWFKLJDQ-UHFFFAOYSA-N

> <FORMULA>
C29H50O3

> <MOLECULAR_WEIGHT>
446.7055

> <EXACT_MASS>
446.375995466

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.216355578100234

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
7.09

> <JCHEM_LOGP>
9.029761174

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.43694867913376

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8580785637670599

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
137.42569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      18.672   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.005   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.340   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.675   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.011   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.344   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.344   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.239   5.184   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.673   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.007   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.342   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.339   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.006   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.674   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.341   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.008   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.677   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.676   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.343   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.340   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.675   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.678   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      41.344   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.344   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      40.010   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      42.678   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.010   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      36.009   3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      44.011   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      38.677   6.930   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      36.779   2.516   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8   29                                                            
CONECT    9   12   13                                                       
CONECT   10   14   15                                                       
CONECT   11   16   18                                                       
CONECT   12    9   20                                                       
CONECT   13    9   21                                                       
CONECT   14   10   21                                                       
CONECT   15   10   22                                                       
CONECT   16   11   22                                                       
CONECT   17   19   26                                                       
CONECT   18   11   29                                                       
CONECT   19   17   29                                                       
CONECT   20    1    2   12                                                  
CONECT   21    3   13   14                                                  
CONECT   22    4   15   16                                                  
CONECT   23    5   24   27                                                  
CONECT   24    6   23   28                                                  
CONECT   25    7   26   27                                                  
CONECT   26   17   25   28                                                  
CONECT   27   23   25   30                                                  
CONECT   28   24   26   31                                                  
CONECT   29    8   18   19   32                                             
CONECT   30   27                                                            
CONECT   31   28                                                            
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
a-Tocopherolquinone	Generator
Α-tocopherolquinone	Generator
a-Tocopheryl quinone	HMDB
a-Tocoquinone	HMDB
alpha-Tocopherol quinone	HMDB
alpha-Tocopheroquinone	HMDB
alpha-Tocopheryl quinone	HMDB
D 178	HMDB
Eutrophyl	HMDB
Ipotensil	HMDB
Metorena	HMDB
Tensiopress	HMDB
Trimina	HMDB
Vitapressina	HMDB
delta-Tocopherylquinone	MeSH
2 (3-Hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinone	MeSH
alpha-Tocoquinone	MeSH
Tocopherolquinone	MeSH
Tocopherylquinone, ((3R,7R,11R*)-(+-))-isomer	MeSH
gamma-Tocopherylquinone	MeSH
Tocopherylquinone	MeSH
Vitamin e quinone	MeSH
alpha-Tocopherolquinone	MeSH

Chemical Formula

C₂₉H₅₀O₃

Average Mass

446.7055 Da

Monoisotopic Mass

446.37600 Da

IUPAC Name

2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

7559-04-8

SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O

InChI Identifier

InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3

InChI Key

LTVDFSLWFKLJDQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Beilschmiedia erythrophloia	Plant	KNApSAcK
Beilschmiedia tsangii	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Caulerpa racemosa	LOTUS Database	35616633
Cryptocarya chinensis	LOTUS Database	35616633
Fatoua villosa	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633
Gentiana lutea	Plant	KNApSAcK
Hellenia speciosa	LOTUS Database	35616633
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ixora coccinea	LOTUS Database	35616633
Jurinea deltoidea	LOTUS Database	35616633
Litsea acutivena	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Myriactis humilis	LOTUS Database	35616633
Nepeta tuberosa	LOTUS Database	35616633
Parentucellia latifolia	LOTUS Database	35616633
Photinia lucida	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Selaginella delicatula	LOTUS Database	35616633
Spinacia oleracea	Plant	KNApSAcK
Swertia angustifolia	LOTUS Database	35616633
Synsepalum dulcificum	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Zanthoxylum beecheyanum	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Prenylbenzoquinone
Quinone
P-benzoquinone
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	7.09	ALOGPS
logP	9.03	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	19.44	ChemAxon
pKa (Strongest Basic)	-0.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	137.43 m³·mol⁻¹	ChemAxon
Polarizability	57.22 Å³	ChemAxon
Number of Rings	1	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

HMDB0034408

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012799

KNApSAcK ID

Not Available

Chemspider ID

22627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for alpha-Tocopherolquinone (NP0047963)

MOL for NP0047963 (alpha-Tocopherolquinone)

3D MOL for NP0047963 (alpha-Tocopherolquinone)

3D SDF for NP0047963 (alpha-Tocopherolquinone)

3D-SDF for NP0047963 (alpha-Tocopherolquinone)

PDB for NP0047963 (alpha-Tocopherolquinone)

3D PDB for NP0047963 (alpha-Tocopherolquinone)

SMILES for NP0047963 (alpha-Tocopherolquinone)

INCHI for NP0047963 (alpha-Tocopherolquinone)

Structure for NP0047963 (alpha-Tocopherolquinone)

3D Structure for NP0047963 (alpha-Tocopherolquinone)