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Showing NP-Card for (R)-alpha-Tocotrienol (NP0333824)

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Record Information
Version2.0
Created at2024-09-09 20:42:33 UTC
Updated at2024-09-09 20:42:34 UTC
NP-MRD IDNP0333824
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-alpha-Tocotrienol
DescriptionOccurs in wheat, barley, rye and palm oil. Alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions.; Compared to tocopherols, alpha- Tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentration help to prevent stroke-related neurodegeneration. (PMID: 16771695 ). Alpha- Tocotrienol is found to have vitamine E activity.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333824 ((R)-alpha-Tocotrienol)


  Mrv2104 05242323142D          

 33 34  0  0  0  0            999 V2000
   -7.8126   -3.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0607   -2.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8714   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4340    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9984   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7179   -2.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5287   -0.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -1.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9037   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2465   -0.1108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
Download

3D MOL for NP0333824 ((R)-alpha-Tocotrienol)

Download
3D SDF for NP0333824 ((R)-alpha-Tocotrienol)

  Mrv2104 05242323142D          

 33 34  0  0  0  0            999 V2000
   -7.8126   -3.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0607   -2.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8714   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4340    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4358   -1.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7179   -2.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6233   -1.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5287   -0.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -1.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5304   -2.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3411   -1.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -0.1108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.0882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  0  0  0  0
  6 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 29  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 18  1  0  0  0  0
 12 20  2  0  0  0  0
 13 21  1  0  0  0  0
 14 32  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  1  0  0  0  0
 16 33  1  0  0  0  0
 16 22  2  0  0  0  0
 17 19  1  0  0  0  0
 17 26  1  0  0  0  0
 18 29  1  0  0  0  0
 19 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 27  2  0  0  0  0
 24 28  2  0  0  0  0
 25 26  2  0  0  0  0
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 26 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CCC1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)=C(/C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1/C29H44O2/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/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14-,22-16+

> <INCHI_KEY>
RZFHLOLGZPDCHJ-AZUPUNDDNA-N

> <FORMULA>
C29H44O2

> <MOLECULAR_WEIGHT>
424.669

> <EXACT_MASS>
424.334130657

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.42752890845948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5,7,8-tetramethyl-2-[(3E,7Z)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_LOGP>
9.290978816

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802140056151512

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852669250142677

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
137.92409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,5,7,8-tetramethyl-2-[(3E,7Z)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0333824 ((R)-alpha-Tocotrienol)
Download
PDB for NP0333824 ((R)-alpha-Tocotrienol)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0     -14.583  -6.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.047  -4.171   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.960  -0.742   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.410   0.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.850   2.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.013  -3.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.464  -2.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.377   0.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.540  -5.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.497  -3.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.454  -1.654   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.947  -2.566   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.904  -0.852   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.860   0.863   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.057  -5.350   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.970  -1.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.420  -1.119   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      -7.927  -0.207   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.914  -2.031   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   32   21                                                  
CONECT   15   10   22                                                       
CONECT   16   11   33   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                                                       
CONECT   32   14                                                            
CONECT   33   16                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Download
3D PDB for NP0333824 ((R)-alpha-Tocotrienol)
Download
SMILES for NP0333824 ((R)-alpha-Tocotrienol)
[H]\C(CC\C(C)=C(/[H])CCC1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)=C(/C)CCC=C(C)C
Download
INCHI for NP0333824 ((R)-alpha-Tocotrienol)
InChI=1/C29H44O2/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/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14-,22-16+
Download
View in JSmol
Synonyms
ValueSource
(R)-a-TocotrienolGenerator
(R)-Α-tocotrienolGenerator
Chemical FormulaC29H44O2
Average Mass424.6690 Da
Monoisotopic Mass424.33413 Da
IUPAC Name2,5,7,8-tetramethyl-2-[(3E,7Z)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran-6-ol
Traditional Name2,5,7,8-tetramethyl-2-[(3E,7Z)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran-6-ol
CAS Registry NumberNot Available
SMILES
[H]\C(CC\C(C)=C(/[H])CCC1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)=C(/C)CCC=C(C)C
InChI Identifier
InChI=1/C29H44O2/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/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14-,22-16+
InChI KeyRZFHLOLGZPDCHJ-AZUPUNDDNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassQuinone and hydroquinone lipids  
Direct ParentTocotrienols  
Alternative Parents
Substituents
  • Tocotrienol
    • 

  • Diterpenoid
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP9.29ChemAxon
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 Count9ChemAxon
Refractivity137.92 m³·mol⁻¹ChemAxon
Polarizability53.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References