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Showing NP-Card for (-)-α-tocopherol (NP0194902)

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Record Information
Version2.0
Created at2022-09-04 12:39:31 UTC
Updated at2022-09-04 12:39:31 UTC
NP-MRD IDNP0194902
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-α-tocopherol
Description(-)-Alpha-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. (-)-α-tocopherol is found in Calea jamaicensis, Cystoseira barbata, Euglena gracilis and Piper aduncum. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain (-)-alpha-tocopherol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0194902 ((-)-α-tocopherol)


  Mrv0541 05041412512D          

 33 34  0  0  1  0            999 V2000
    7.1843   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8987   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7566   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6145   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9438   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3189   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4401   -5.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9421   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3277   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1856   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0435   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6132   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0422   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4711   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9000   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3290   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8152   -6.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7579   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0027   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8987   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7566   -5.7803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6145   -5.7803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6617   -3.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8492   -4.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9098   -5.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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  2  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
   10.0422   -6.1928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9000   -6.1928    0.0000 H   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  1  0  0  0
 21 13  1  0  0  0  0
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 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  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  1  0  0  0
 29 18  1  6  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
 21 32  1  6  0  0  0
 22 33  1  6  0  0  0
M  END
Download

3D MOL for NP0194902 ((-)-α-tocopherol)

Download
3D SDF for NP0194902 ((-)-α-tocopherol)

  Mrv0541 05041412512D          

 33 34  0  0  1  0            999 V2000
    7.1843   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8987   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7566   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6145   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9438   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3189   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4401   -5.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9421   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3277   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1856   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0435   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6132   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0422   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4711   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9000   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3290   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8152   -6.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7579   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0027   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8987   -5.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7566   -5.7803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6145   -5.7803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6617   -3.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8492   -4.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9098   -5.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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  2  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
   10.0422   -6.1928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9000   -6.1928    0.0000 H   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  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  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  1  0  0  0
 29 18  1  6  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
 21 32  1  6  0  0  0
 22 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0194902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](C)(CCCC(C)C)CCC[C@]([H])(C)CCC[C@@]1(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/t21-,22-,29-/m0/s1

> <INCHI_KEY>
GVJHHUAWPYXKBD-SYZUXVNWSA-N

> <FORMULA>
C29H50O2

> <MOLECULAR_WEIGHT>
430.7061

> <EXACT_MASS>
430.381080844

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
55.64208773249428

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,5,7,8-tetramethyl-2-[(4S,8S)-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>
(-)-α-tocopherol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0194902 ((-)-α-tocopherol)
Download
PDB for NP0194902 ((-)-α-tocopherol)
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  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   33  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   32                                             
CONECT   22    4   15   16   33                                             
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                                                       
CONECT   32   21                                                            
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Download
3D PDB for NP0194902 ((-)-α-tocopherol)
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SMILES for NP0194902 ((-)-α-tocopherol)
[H][C@](C)(CCCC(C)C)CCC[C@]([H])(C)CCC[C@@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1
Download
INCHI for NP0194902 ((-)-α-tocopherol)
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/t21-,22-,29-/m0/s1
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View in JSmol
Synonyms
ValueSource
VITAMIN eChEBI
(-)-a-TocopherolGenerator
(-)-Α-tocopherolGenerator
Chemical FormulaC29H50O2
Average Mass430.7061 Da
Monoisotopic Mass430.38108 Da
IUPAC Name(2S)-2,5,7,8-tetramethyl-2-[(4S,8S)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name(-)-α-tocopherol
CAS Registry NumberNot Available
SMILES
[H][C@](C)(CCCC(C)C)CCC[C@]([H])(C)CCC[C@@]1(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/t21-,22-,29-/m0/s1
InChI KeyGVJHHUAWPYXKBD-SYZUXVNWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calea jamaicensisLOTUS Database
Cystoseira barbataLOTUS Database
Euglena gracilisLOTUS Database
Piper aduncumLOTUS Database
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassQuinone and hydroquinone lipids  
Direct ParentTocopherols  
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.84ALOGPS
logP10.51ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity135.37 m³·mol⁻¹ChemAxon
Polarizability55.64 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1742129  
PDB IDNot Available
ChEBI ID46430  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]