NP-MRD: Showing NP-Card for β-tocopherol (NP0246915)

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Record Information

Version

1.0

Created at

2022-09-07 08:32:14 UTC

Updated at

2022-09-07 08:32:14 UTC

NP-MRD ID

NP0246915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-tocopherol

Description

β-Tocopherol belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. β-tocopherol is found in Cupania latifolia. β-Tocopherol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305221920202D          

 30 31  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652305221920202D          

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M  END
> <DATABASE_ID>
NP0246915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=C(C)C(O)=CC(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3

> <INCHI_KEY>
WGVKWNUPNGFDFJ-UHFFFAOYSA-N

> <FORMULA>
C28H48O2

> <MOLECULAR_WEIGHT>
416.6795

> <EXACT_MASS>
416.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.03868291415948

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.81

> <JCHEM_LOGP>
9.994295870666667

> <ALOGPS_LOGS>
-7.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.47268342050907

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852415884494152

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
130.33289999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.26e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-tocopherol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      13.411 -10.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.744 -12.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.079 -12.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.414 -12.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.329  -6.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.288 -11.167   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.759 -11.970   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.412 -10.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.746 -10.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.081 -10.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.078 -10.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.745 -10.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.413 -10.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.080 -10.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.747 -10.020   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.255 -11.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.415 -10.020   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.738 -11.970   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.835  -7.361   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.744 -10.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.079 -10.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.414 -10.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.318  -7.628   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.298  -9.988   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.782 -10.255   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.825  -8.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.792  -9.075   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.748 -10.790   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      37.342  -8.273   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      31.275  -9.343   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   28                                                            
CONECT    8   11   12                                                       
CONECT    9   13   14                                                       
CONECT   10   15   17                                                       
CONECT   11    8   20                                                       
CONECT   12    8   21                                                       
CONECT   13    9   21                                                       
CONECT   14    9   22                                                       
CONECT   15   10   22                                                       
CONECT   16   18   25                                                       
CONECT   17   10   28                                                       
CONECT   18   16   28                                                       
CONECT   19   23   26                                                       
CONECT   20    1    2   11                                                  
CONECT   21    3   12   13                                                  
CONECT   22    4   14   15                                                  
CONECT   23    5   19   27                                                  
CONECT   24    6   25   26                                                  
CONECT   25   16   24   27                                                  
CONECT   26   19   24   29                                                  
CONECT   27   23   25   30                                                  
CONECT   28    7   17   18   30                                             
CONECT   29   26                                                            
CONECT   30   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₈O₂

Average Mass

416.6795 Da

Monoisotopic Mass

416.36543 Da

IUPAC Name

2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

β-tocopherol

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=C(C)C(O)=CC(C)=C2O1

InChI Identifier

InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3

InChI Key

WGVKWNUPNGFDFJ-UHFFFAOYSA-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
Cupania latifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
Diterpenoid
1-benzopyran
Benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

vitamin E (BETA-TOCOPHEROL )

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	8.81	ALOGPS
logP	9.99	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	130.33 m³·mol⁻¹	ChemAxon
Polarizability	54.04 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

FDB031301

KNApSAcK ID

Not Available

Chemspider ID

77632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tocopherol

METLIN ID

Not Available

PubChem Compound

86052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for β-tocopherol (NP0246915)

MOL for NP0246915 (β-tocopherol)

3D MOL for NP0246915 (β-tocopherol)

3D SDF for NP0246915 (β-tocopherol)

3D-SDF for NP0246915 (β-tocopherol)

PDB for NP0246915 (β-tocopherol)

3D PDB for NP0246915 (β-tocopherol)

SMILES for NP0246915 (β-tocopherol)

INCHI for NP0246915 (β-tocopherol)

Structure for NP0246915 (β-tocopherol)

3D Structure for NP0246915 (β-tocopherol)