NP-MRD: Showing NP-Card for R-δ-tocotrienol (NP0014309)

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Record Information

Version

2.0

Created at

2021-01-05 23:30:52 UTC

Updated at

2021-08-19 23:59:52 UTC

NP-MRD ID

NP0014309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

R-δ-tocotrienol

Provided By

NPAtlas

Description

Delta-Tocotrienol, also known as δ-tocotrienol or tocotrienol, delta, 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, delta-tocotrienol is considered to be a quinone. Delta-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Delta-Tocotrienol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. R-δ-tocotrienol is found in Bixa orellana, Cratoxylum cochinchinense, Cystophora monilifera, Garcinia kola, Kielmeyera coriacea, Kielmeyera lathrophyton, Kielmeyera reticulata and Sargassum siliquastrum. R-δ-tocotrienol was first documented in 2011 (PMID: 21598300). Based on a literature review a small amount of articles have been published on delta-Tocotrienol (PMID: 22816285) (PMID: 24486300) (PMID: 24294967).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119543D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242119543D          

 69 70  0  0  0  0            999 V2000
    6.8535    1.4426   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5614    0.4094    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3807    0.8033    1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4393   -0.8611   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6339   -1.3155   -1.3916 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5204   -2.2294   -1.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5444   -1.5794   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9401   -1.1063    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -1.4298   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2075   -0.8061    0.3428 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6332    0.3797   -0.3794 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5714    1.0709    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    1.7048    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    1.1381   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626    1.8193    0.4091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8424    0.8708    0.8027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5299    0.0983   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6735   -0.8281   -1.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    1.0602   -1.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3608    0.3903   -1.9495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3655    0.1013   -0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7009    0.3533   -1.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5271    0.0465    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8913    0.2909   -0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0411   -0.5000    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6864   -0.7583    1.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1585   -1.3457    2.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8761   -0.4404    0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342   -0.6791    0.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3523    1.6053   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8977    2.4075   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7975    1.1535   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3178    1.2937    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6170   -0.0349    1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.6032    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658   -1.6194    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012   -0.4726   -2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3469   -1.9052   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870   -2.6457   -1.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9182   -3.1154   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -1.4366    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274    0.0019    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9362   -1.5246    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0200   -1.8113   -1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501   -1.5313    0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751   -0.5961    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783    0.0299   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4311    1.1439   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    1.3277    2.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564    1.5140    2.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562    2.8101    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670    0.7094   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561    2.6389   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    2.4117    1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    0.0754    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3134   -1.7710   -1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986   -0.5069   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921   -1.2250   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2904    0.6883   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9588   -1.8954    3.1501 H   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  3  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
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 17  1  0  0  0  0
 28 21  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  0  0  0  0
 10 45  1  0  0  0  0
 10 46  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
 13 49  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
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 16 55  1  0  0  0  0
 16 56  1  0  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 18 59  1  0  0  0  0
 19 60  1  0  0  0  0
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 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 22 64  1  0  0  0  0
 24 65  1  0  0  0  0
 25 66  1  0  0  0  0
 27 67  1  0  0  0  0
 27 68  1  0  0  0  0
 27 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C2O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1

> <INCHI_KEY>
ODADKLYLWWCHNB-LDYBVBFYSA-N

> <FORMULA>
C27H40O2

> <MOLECULAR_WEIGHT>
396.615

> <EXACT_MASS>
396.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.8035018709632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
8.264136037333332

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141674654384879

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85227174738162

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
127.84169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delta tocotrienol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
    6.8535    1.4426   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5614    0.4094    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3807    0.8033    1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4393   -0.8611   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6339   -1.3155   -1.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5204   -2.2294   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5444   -1.5794   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9401   -1.1063    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -1.4298   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2075   -0.8061    0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    0.3797   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    1.0709    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    1.7048    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    1.1381   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626    1.8193    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    0.8708    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5299    0.0983   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6735   -0.8281   -1.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    1.0602   -1.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3655    0.1013   -0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7009    0.3533   -1.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2904    0.6883   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9588   -1.8954    3.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 17 16  1  1
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 17  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 24 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.854   1.443  -0.678  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.561   0.409   0.115  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.381   0.803   1.274  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.439  -0.861  -0.241  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.634  -1.315  -1.392  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.520  -2.229  -1.028  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.544  -1.579  -0.103  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.940  -1.106   1.225  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.270  -1.430  -0.473  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.208  -0.806   0.343  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.633   0.380  -0.379  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.571   1.071   0.343  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.684   1.705   1.665  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.645   1.138  -0.259  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.763   1.819   0.409  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.842   0.871   0.803  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.530   0.098  -0.266  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.674  -0.828  -1.058  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.190   1.060  -1.255  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.361   0.390  -1.950  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.365   0.101  -0.872  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.701   0.353  -1.010  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.527   0.047   0.047  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.891   0.291  -0.062  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.041  -0.500   1.220  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.686  -0.758   1.366  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.159  -1.346   2.625  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.876  -0.440   0.288  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.534  -0.679   0.390  0.00  0.00           O+0
HETATM   30  H   UNK     0       7.352   1.605  -1.659  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.898   2.408  -0.145  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.798   1.153  -0.914  0.00  0.00           H+0
HETATM   33  H   UNK     0       9.318   1.294   0.880  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.617  -0.035   1.955  0.00  0.00           H+0
HETATM   35  H   UNK     0       7.859   1.603   1.845  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.966  -1.619   0.340  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.301  -0.473  -2.035  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.347  -1.905  -2.043  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.987  -2.646  -1.894  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.918  -3.115  -0.455  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.246  -1.437   2.030  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.927   0.002   1.252  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.936  -1.525   1.560  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.020  -1.811  -1.470  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.350  -1.531   0.467  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.575  -0.596   1.337  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.278   0.030  -1.366  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.431   1.144  -0.614  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.076   1.328   2.380  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.656   1.514   2.162  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.556   2.810   1.609  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.767   0.709  -1.252  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.156   2.639  -0.257  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.402   2.412   1.311  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.410   0.075   1.507  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.592   1.372   1.481  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.313  -1.771  -1.220  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.499  -0.507  -2.115  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.792  -1.225  -0.546  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.431   1.270  -2.036  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.476   1.976  -0.738  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.998  -0.568  -2.337  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.746   1.087  -2.703  0.00  0.00           H+0
HETATM   64  H   UNK     0      -8.050   0.783  -1.945  0.00  0.00           H+0
HETATM   65  H   UNK     0     -10.290   0.688  -0.898  0.00  0.00           H+0
HETATM   66  H   UNK     0      -8.738  -0.722   2.020  0.00  0.00           H+0
HETATM   67  H   UNK     0      -5.721  -0.549   3.288  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.375  -2.073   2.340  0.00  0.00           H+0
HETATM   69  H   UNK     0      -6.959  -1.895   3.150  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   33   34   35                                             
CONECT    4    2    5   36                                                  
CONECT    5    4    6   37   38                                             
CONECT    6    5    7   39   40                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   41   42   43                                             
CONECT    9    7   10   44                                                  
CONECT   10    9   11   45   46                                             
CONECT   11   10   12   47   48                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   49   50   51                                             
CONECT   14   12   15   52                                                  
CONECT   15   14   16   53   54                                             
CONECT   16   15   17   55   56                                             
CONECT   17   16   18   19   29                                             
CONECT   18   17   57   58   59                                             
CONECT   19   17   20   60   61                                             
CONECT   20   19   21   62   63                                             
CONECT   21   20   22   28                                                  
CONECT   22   21   23   64                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   65                                                       
CONECT   25   23   26   66                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   67   68   69                                             
CONECT   28   26   29   21                                                  
CONECT   29   28   17                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   13                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   19                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   22                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   27                                                            
CONECT   68   27                                                            
CONECT   69   27                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  140    0
END

RDKit          3D

69 70  0  0  0  0  0  0  0  0999 V2000
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    4.2462   -1.4366    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274    0.0019    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2904    0.6883   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7381   -0.7217    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208   -0.5494    3.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3751   -2.0729    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9588   -1.8954    3.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 17 16  1  1
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 17  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 24 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R)-2,8-Dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
Δ-tocotrienol	Generator
Tocotrienol, delta	HMDB
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-ol	HMDB
(R)-delta-Tocotrienol	HMDB
(R)-Δ-tocotrienol	HMDB
8-Methyltocotrienol	HMDB
D-delta-Tocotrienol	HMDB
D-Δ-tocotrienol	HMDB
delta-Tocotrienol	HMDB

Chemical Formula

C₂₇H₄₀O₂

Average Mass

396.6150 Da

Monoisotopic Mass

396.30283 Da

IUPAC Name

(2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

delta tocotrienol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1

InChI Key

ODADKLYLWWCHNB-LDYBVBFYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aesculus hippocastanum Hort.	KNApSAcK Database	22123792
Amaranthus hypochondriacus L.	KNApSAcK Database	22123792
Avena sativa L.	KNApSAcK Database	22123792
Bixa orellana	LOTUS Database	35616633
Bixa orellana L.	KNApSAcK Database	22123792
Calophyllum inophyllum L.	KNApSAcK Database	22123792
Carum carvi L.	KNApSAcK Database	22123792
Cinnamosma fragrans	KNApSAcK Database	22123792
Cinnamosma macrocarpa	KNApSAcK Database	22123792
Cinnamosma madagascariensis	KNApSAcK Database	22123792
Cocos nucifera L.	KNApSAcK Database	22123792
Coriandrum sativum L.	KNApSAcK Database	22123792
Cratoxylum cochinchinense	LOTUS Database	35616633
Cratoxylum sumatranum	KNApSAcK Database	22123792
Cystophora monilifera	NPAtlas	26093325
Elaeis guineensis Jacq.	KNApSAcK Database	22123792
Foeniculum vulgare L.	KNApSAcK Database	22123792
Garcinia kola	LOTUS Database	35616633
Garcinia multiflora	KNApSAcK Database	22123792
Hevea brasiliensis Mull.Arg.	KNApSAcK Database	22123792
Hordeum vulgare L.	KNApSAcK Database	22123792
Juglans regia L.	KNApSAcK Database	22123792
Kielmeyera coriacea	LOTUS Database	35616633
Kielmeyera lathrophyton	LOTUS Database	35616633
Kielmeyera reticulata	LOTUS Database	35616633
Litchi chinensis Sonn.	KNApSAcK Database	22123792
Nicotiana tabacum L.	KNApSAcK Database	22123792
Oryza sativa L.	KNApSAcK Database	22123792
Pleodendron costaricense	KNApSAcK Database	22123792
Rosmarinus officinalis L.	KNApSAcK Database	22123792
Sargassum siliquastrum	LOTUS Database	35616633
Vaccinium macrocarpon Aiton	KNApSAcK Database	22123792
Zea mays L.	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

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	517.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.9e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.840 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	7.71	ALOGPS
logP	8.26	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	10.14	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	9	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	49.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019103

HMDB ID

HMDB0030008

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tocotrienol

METLIN ID

Not Available

PubChem Compound

5282350

PDB ID

Not Available

ChEBI ID

33276

Good Scents ID

rw1679291

References

General References

Ji X, Wang Z, Geamanu A, Sarkar FH, Gupta SV: Inhibition of cell growth and induction of apoptosis in non-small cell lung cancer cells by delta-tocotrienol is associated with notch-1 down-regulation. J Cell Biochem. 2011 Oct;112(10):2773-83. doi: 10.1002/jcb.23184. [PubMed:21598300 ]
Asakawa Y, Ludwiczuk A, Harinantenaina L, Toyota M, Nishiki M, Bardon A, Nii K: Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species. Nat Prod Commun. 2012 Jun;7(6):685-92. [PubMed:22816285 ]
Singh VK, Wise SY, Scott JR, Romaine PL, Newman VL, Fatanmi OO: Radioprotective efficacy of delta-tocotrienol, a vitamin E isoform, is mediated through granulocyte colony-stimulating factor. Life Sci. 2014 Mar 11;98(2):113-22. doi: 10.1016/j.lfs.2014.01.065. Epub 2014 Jan 28. [PubMed:24486300 ]
Li XH, Ghosh SP, Ha CT, Fu D, Elliott TB, Bolduc DL, Villa V, Whitnall MH, Landauer MR, Xiao M: Delta-tocotrienol protects mice from radiation-induced gastrointestinal injury. Radiat Res. 2013 Dec;180(6):649-57. doi: 10.1667/RR13398.1. Epub 2013 Dec 2. [PubMed:24294967 ]

Showing NP-Card for R-δ-tocotrienol (NP0014309)

MOL for NP0014309 (R-δ-tocotrienol)

3D MOL for NP0014309 (R-δ-tocotrienol)

3D SDF for NP0014309 (R-δ-tocotrienol)

3D-SDF for NP0014309 (R-δ-tocotrienol)

PDB for NP0014309 (R-δ-tocotrienol)

3D PDB for NP0014309 (R-δ-tocotrienol)

SMILES for NP0014309 (R-δ-tocotrienol)

INCHI for NP0014309 (R-δ-tocotrienol)

Structure for NP0014309 (R-δ-tocotrienol)

3D Structure for NP0014309 (R-δ-tocotrienol)