NP-MRD: Showing NP-Card for α-tocopherylquinone (NP0264502)

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Record Information

Version

1.0

Created at

2022-09-08 08:03:23 UTC

Updated at

2022-09-08 08:03:23 UTC

NP-MRD ID

NP0264502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-tocopherylquinone

Description

2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. α-tocopherylquinone is found in Beilschmiedia erythrophloia, Beilschmiedia tsangii, Caulerpa racemosa, Cryptocarya chinensis, Garcinia multiflora, Himalaiella deltoidea, Litsea acutivena, Muntingia calabura, Myriactis humilis, Parentucellia latifolia, Photinia lucida, Selaginella delicatula, Swertia angustifolia, Synsepalum dulcificum and Vitex negundo. 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041412562D          

 34 34  0  0  1  0            999 V2000
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   21.4341    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 32  1  1  0  0  0
 21 33  1  6  0  0  0
 22 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05041412562D          

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 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  1  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  4  1  1  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  1  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
 29 32  1  1  0  0  0
 21 33  1  6  0  0  0
 22 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0264502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@@](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/t21-,22-,29-/m1/s1

> <INCHI_KEY>
LTVDFSLWFKLJDQ-IEOSBIPESA-N

> <FORMULA>
C29H50O3

> <MOLECULAR_WEIGHT>
446.7055

> <EXACT_MASS>
446.375995466

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.207617571598725

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+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   33                                             
CONECT   22    4   15   16   34                                             
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                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
Alpha-Tocopherylquinone	ChEMBL
a-Tocopherylquinone	Generator
α-tocopherylquinone	Generator
a-Tocopherolquinone	Generator
α-tocopherolquinone	Generator
alpha-Tocopherol quinone	MeSH
delta-Tocopherylquinone	MeSH
alpha-Tocopheryl quinone	MeSH
Tocopherylquinone, ((3R,7R,11R*)-(+-))-isomer	MeSH
Eutrophyl	MeSH
alpha-Tocoquinone	MeSH
gamma-Tocopherylquinone	MeSH
Tocopherylquinone	MeSH
Vitamin e quinone	MeSH
2 (3-Hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinone	MeSH
Tocopherolquinone	MeSH

Chemical Formula

C₂₉H₅₀O₃

Average Mass

446.7055 Da

Monoisotopic Mass

446.37600 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@@](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/t21-,22-,29-/m1/s1

InChI Key

LTVDFSLWFKLJDQ-IEOSBIPESA-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
Beilschmiedia erythrophloia	LOTUS Database	35616633
Beilschmiedia tsangii	LOTUS Database	35616633
Caulerpa racemosa	LOTUS Database	35616633
Cryptocarya chinensis	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633
Jurinea deltoidea	LOTUS Database	35616633
Litsea acutivena	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Myriactis humilis	LOTUS Database	35616633
Parentucellia latifolia	LOTUS Database	35616633
Photinia lucida	LOTUS Database	35616633
Selaginella delicatula	LOTUS Database	35616633
Swertia angustifolia	LOTUS Database	35616633
Synsepalum dulcificum	LOTUS Database	35616633
Vitex negundo	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

organic molecular entity (CHEBI:46468 )

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	57.21 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

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2734086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for α-tocopherylquinone (NP0264502)

MOL for NP0264502 (α-tocopherylquinone)

3D MOL for NP0264502 (α-tocopherylquinone)

3D SDF for NP0264502 (α-tocopherylquinone)

3D-SDF for NP0264502 (α-tocopherylquinone)

PDB for NP0264502 (α-tocopherylquinone)

3D PDB for NP0264502 (α-tocopherylquinone)

SMILES for NP0264502 (α-tocopherylquinone)

INCHI for NP0264502 (α-tocopherylquinone)

Structure for NP0264502 (α-tocopherylquinone)

3D Structure for NP0264502 (α-tocopherylquinone)