NP-MRD: Showing NP-Card for (2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol (NP0173821)

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Record Information

Version

2.0

Created at

2022-09-03 11:00:36 UTC

Updated at

2022-09-03 11:00:36 UTC

NP-MRD ID

NP0173821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol

Description

Plastochromanol-8, also known as gamma-tocotrienol or tocotrienol, gamma, 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. Thus, plastochromanol-8 is considered to be a quinone. (2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol is found in Cucumaria frondosa and Dioscorea alata. (2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol was first documented in 2020 (PMID: 32931882). Based on a literature review a small amount of articles have been published on Plastochromanol-8 (PMID: 35888732) (PMID: 35404409) (PMID: 33556703) (PMID: 33483975).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213002D          

 55 56  0  0  1  0            999 V2000
  -17.6121   13.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7997   13.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2694   14.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5175   12.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7050   12.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4229   11.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6104   11.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0801   12.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3282   10.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5158   10.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2336    9.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4211    9.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8908   10.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1390    9.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3265    8.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0443    8.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2319    7.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7016    8.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0426    6.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5123    6.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7604    5.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9480    5.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6658    4.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3819    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  6  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
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 48 50  2  0  0  0  0
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 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 46 54  1  0  0  0  0
 54 55  1  0  0  0  0
 42 55  1  0  0  0  0
M  END

     RDKit          3D

137138  0  0  0  0  0  0  0  0999 V2000
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   -8.0323   -0.9909    2.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4835    1.0489    0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7759    1.8426   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0558    3.1022   -2.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    1.7538   -2.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0200    0.9022   -2.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2358    1.0352    1.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032213002D          

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 42 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C53H82O2/c1-40(2)21-13-22-41(3)23-14-24-42(4)25-15-26-43(5)27-16-28-44(6)29-17-30-45(7)31-18-32-46(8)33-19-34-47(9)35-20-37-53(12)38-36-50-39-51(54)48(10)49(11)52(50)55-53/h21,23,25,27,29,31,33,35,39,54H,13-20,22,24,26,28,30,32,34,36-38H2,1-12H3/b41-23+,42-25+,43-27+,44-29+,45-31+,46-33+,47-35+/t53-/m1/s1

> <INCHI_KEY>
PTMZTTPJFDLIOR-HCCCIJMNSA-N

> <FORMULA>
C53H82O2

> <MOLECULAR_WEIGHT>
751.237

> <EXACT_MASS>
750.63148188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
137

> <JCHEM_AVERAGE_POLARIZABILITY>
100.31931971467921

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,7,8-trimethyl-2-[(3E,7E,11E,15E,19E,23E,27E)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
10.20

> <JCHEM_LOGP>
17.07612880166667

> <ALOGPS_LOGS>
-6.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.47042231417464

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852470626655554

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
251.89590000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,7,8-trimethyl-2-[(3E,7E,11E,15E,19E,23E,27E)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0     -32.876  25.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -31.359  25.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -30.369  26.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -30.833  23.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -29.316  23.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -28.789  21.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -27.273  21.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -26.283  22.873   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -26.746  20.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -25.229  19.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -24.703  18.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -23.186  18.265   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -22.196  19.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -22.659  16.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -21.143  16.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -20.616  15.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -19.099  14.835   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -18.110  16.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -18.573  13.388   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.056  13.121   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -16.529  11.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -15.013  11.406   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.023  12.586   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.486   9.959   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.970   9.692   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.443   8.245   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.926   7.977   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.936   9.157   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.399   6.530   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.883   6.263   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.356   4.816   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.840   4.548   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.850   5.728   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.313   3.101   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.796   2.834   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.270   1.387   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.753   1.119   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.763   2.299   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44   55                                             
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   46   55                                                  
CONECT   55   54   42                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  112    0
END

View in JSmol

Synonyms

Value	Source
gamma-Tocotrienol	MeSH
Tocotrienol, gamma	MeSH

Chemical Formula

C₅₃H₈₂O₂

Average Mass

751.2370 Da

Monoisotopic Mass

750.63148 Da

IUPAC Name

(2R)-2,7,8-trimethyl-2-[(3E,7E,11E,15E,19E,23E,27E)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2R)-2,7,8-trimethyl-2-[(3E,7E,11E,15E,19E,23E,27E)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1

InChI Identifier

InChI=1S/C53H82O2/c1-40(2)21-13-22-41(3)23-14-24-42(4)25-15-26-43(5)27-16-28-44(6)29-17-30-45(7)31-18-32-46(8)33-19-34-47(9)35-20-37-53(12)38-36-50-39-51(54)48(10)49(11)52(50)55-53/h21,23,25,27,29,31,33,35,39,54H,13-20,22,24,26,28,30,32,34,36-38H2,1-12H3/b41-23+,42-25+,43-27+,44-29+,45-31+,46-33+,47-35+/t53-/m1/s1

InChI Key

PTMZTTPJFDLIOR-HCCCIJMNSA-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
Cucumaria frondosa	LOTUS Database	35616633
Dioscorea alata	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Polyterpenoid
Tocotrienol
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

Not Available

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	10.2	ALOGPS
logP	17.08	ChemAxon
logS	-6.7	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	24	ChemAxon
Refractivity	251.9 m³·mol⁻¹	ChemAxon
Polarizability	100.32 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

Not Available

KNApSAcK ID

C00057391

Chemspider ID

4942816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438333

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Trela-Makowej A, Leskiewicz M, Kruk J, Zadlo A, Basta-Kaim A, Szymanska R: Antioxidant and Neuroprotective Activity of Vitamin E Homologues: In Vitro Study. Metabolites. 2022 Jun 30;12(7):608. doi: 10.3390/metabo12070608. [PubMed:35888732 ]
Kim I, Kim EH, Choi YR, Kim HU: Fibrillin2 in chloroplast plastoglobules participates in photoprotection and jasmonate-induced senescence. Plant Physiol. 2022 Jun 27;189(3):1363-1379. doi: 10.1093/plphys/kiac166. [PubMed:35404409 ]
Kruk J, Szymanska R: Singlet oxygen oxidation products of carotenoids, fatty acids and phenolic prenyllipids. J Photochem Photobiol B. 2021 Mar;216:112148. doi: 10.1016/j.jphotobiol.2021.112148. Epub 2021 Jan 31. [PubMed:33556703 ]
Fernandez-Marin B, Saenz-Ceniceros A, Solanki T, Robson TM, Garcia-Plazaola JI: Alpine forbs rely on different photoprotective strategies during spring snowmelt. Physiol Plant. 2021 Jul;172(3):1506-1517. doi: 10.1111/ppl.13342. Epub 2021 Feb 16. [PubMed:33483975 ]
Kumar A, Prasad A, Sedlarova M, Ksas B, Havaux M, Pospisil P: Interplay between antioxidants in response to photooxidative stress in Arabidopsis. Free Radic Biol Med. 2020 Nov 20;160:894-907. doi: 10.1016/j.freeradbiomed.2020.08.027. Epub 2020 Sep 12. [PubMed:32931882 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol (NP0173821)

MOL for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

3D MOL for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

3D SDF for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

3D-SDF for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

PDB for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

3D PDB for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

SMILES for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

INCHI for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

Structure for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)

3D Structure for NP0173821 ((2r)-2,7,8-trimethyl-2-[(3e,7e,11e,15e,19e,23e,27e)-4,8,12,16,20,24,28,32-octamethyltritriaconta-3,7,11,15,19,23,27,31-octaen-1-yl]-3,4-dihydro-1-benzopyran-6-ol)