NP-MRD: Showing NP-Card for vita e (NP0270525)

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Record Information

Version

2.0

Created at

2022-09-08 16:29:06 UTC

Updated at

2022-09-08 16:29:06 UTC

NP-MRD ID

NP0270525

Secondary Accession Numbers

None

Natural Product Identification

Common Name

vita e

Description

α-Tocopherol, also known as vitamin e, 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. α-Tocopherol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, α-tocopherol has been detected, but not quantified in, several different foods, such as german camomiles, summer savories, abiyuchs, common buckwheats, and hyacinth beans. This could make α-tocopherol a potential biomarker for the consumption of these foods. α-Tocopherol has three stereocenters, so it is a chiral molecule. This mix of stereoisomers is often called dl-α-tocopheryl acetate. The SRR may be named 2-epi-α-tocopherol, the diastereomeric mixture of RRR-α-tocopherol and 2-epi-α-tocopherol may be called 2-ambo-α-tocopherol (formerly named dl-α-tocopherol). However, 1 IU of this mixture of diastereomers is not now considered equivalent to 1 IU of natural RRR-α-tocopherol, and the Institute of Medicine and the USDA now convert IUs of the racemic mixture to milligrams of equivalent RRR using 1 IU racemic mixture 0.45 "Mg α-tocopherol". Older name of RRR-α-tocopherol is d-α-tocopherol, but this d/l naming should be no longer used, because whether l-α-tocopherol should mean SSS enantiomer or the SRR diastereomer is not clear, from historical reasons. The mixture of all eight diastereomers is called all-rac-α-tocopherolOne IU of tocopherol is defined as ⅔ milligrams of RRR-α-tocopherol (formerly named d-α-tocopherol, or sometimes ddd-α-tocopherol). The eight stereoisomers of α-tocopherol differ the configuration on these stereocenters. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. α-Tocopherol is a type of vitamin E. It has E number "E307". vita e is found in Acca sellowiana, Albifimbria verrucaria, Antidesma pentandrum, Calea jamaicensis, Corymbia citriodora, Cupania americana, Cystoseira barbata, Daphne gnidium, Dictyota dichotoma, Dioscorea alata, Diospyros maritima, Euglena gracilis, Euscaphis japonica, Ficus pumila, Fossombronia alaskana, Goniophlebium mengtzeense, Hemerocallis fulva, Labisia pumila, Litsea acutivena, Machilus zuihoensis, Neolitsea hiiranensis, Oncorhynchus keta, Piper aduncum, Piper guineense, Pittosporum tobira, Rhododendron formosanum, Rhodomyrtus tomentosa, Trichilia claussenii, Vaccinium myrtillus and Xylocarpus granatum. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081715502D          

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M  END

     RDKit          3D

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M  END


  Mrv1652310081715502D          

 31 32  0  0  0  0            999 V2000
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   18.0973   -5.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1920   -4.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5670   -4.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4724   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0044   -4.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7546   -5.0050    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  1  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  2  0  0  0  0
 27 25  1  0  0  0  0
 28 24  2  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  1  0  0  0  0
 31 28  1  0  0  0  0
 31 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270525

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3

> <INCHI_KEY>
GVJHHUAWPYXKBD-UHFFFAOYSA-N

> <FORMULA>
C29H50O2

> <MOLECULAR_WEIGHT>
430.717

> <EXACT_MASS>
430.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.1786256708737

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.84

> <JCHEM_LOGP>
10.507717260000002

> <ALOGPS_LOGS>
-7.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802178125613777

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852614901775799

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
135.37409999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.04e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vita E

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         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      35.362  -5.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.329  -6.448   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.288 -11.167   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.759 -11.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.412 -10.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.746 -10.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.081 -10.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.078 -10.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.745 -10.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.413 -10.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.080 -10.020   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.747 -10.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.255 -11.702   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.415 -10.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.738 -11.970   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      34.835  -7.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.318  -7.628   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.298  -9.988   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      33.782 -10.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.825  -8.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.792  -9.075   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.748 -10.790   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      37.342  -8.273   0.000  0.00  0.00           O+0
HETATM   31  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   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   31                                             
CONECT   30   27                                                            
CONECT   31   28   29                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Vitamin e	MeSH

Chemical Formula

C₂₉H₅₀O₂

Average Mass

430.7170 Da

Monoisotopic Mass

430.38108 Da

IUPAC Name

2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

vita E

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3

InChI Key

GVJHHUAWPYXKBD-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
Acca sellowiana	LOTUS Database	35616633
Albifimbria verrucaria	LOTUS Database	35616633
Antidesma pentandrum	LOTUS Database	35616633
Calea jamaicensis	LOTUS Database	35616633
Corymbia citriodora	LOTUS Database	35616633
Cupania americana	LOTUS Database	35616633
Cystoseira barbata	LOTUS Database	35616633
Daphne gnidium	LOTUS Database	35616633
Dictyota dichotoma	LOTUS Database	35616633
Dioscorea alata	LOTUS Database	35616633
Diospyros maritima	LOTUS Database	35616633
Euglena gracilis	LOTUS Database	35616633
Euscaphis japonica	LOTUS Database	35616633
Ficus pumila	LOTUS Database	35616633
Fossombronia alaskana	LOTUS Database	35616633
Goniophlebium mengtzeense	LOTUS Database	35616633
Hemerocallis fulva	LOTUS Database	35616633
Labisia pumila	LOTUS Database	35616633
Litsea acutivena	LOTUS Database	35616633
Machilus zuihoensis	LOTUS Database	35616633
Neolitsea hiiranensis	LOTUS Database	35616633
Oncorhynchus keta	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Pittosporum tobira	LOTUS Database	35616633
Rhododendron formosanum	LOTUS Database	35616633
Rhodomyrtus tomentosa	LOTUS Database	35616633
Trichilia claussenii	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633
Xylocarpus granatum	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
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 (ALPHA-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	8.84	ALOGPS
logP	10.51	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	10.8	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	135.37 m³·mol⁻¹	ChemAxon
Polarizability	56.18 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

HMDB0165342

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031279

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Tocopherol

METLIN ID

Not Available

PubChem Compound

2116

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for vita e (NP0270525)

MOL for NP0270525 (vita e)

3D MOL for NP0270525 (vita e)

3D SDF for NP0270525 (vita e)

3D-SDF for NP0270525 (vita e)

PDB for NP0270525 (vita e)

3D PDB for NP0270525 (vita e)

SMILES for NP0270525 (vita e)

INCHI for NP0270525 (vita e)

Structure for NP0270525 (vita e)

3D Structure for NP0270525 (vita e)