NP-MRD: Showing NP-Card for 13'-Hydroxy-gamma-tocotrienol (NP0339046)

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Record Information

Version

2.0

Created at

2024-09-11 19:25:39 UTC

Updated at

2024-09-11 19:25:40 UTC

NP-MRD ID

NP0339046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13'-Hydroxy-gamma-tocotrienol

Description

13'-Hydroxy-gamma-tocotrienol, also known as 13OHGAMMATE, 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. 13'-Hydroxy-gamma-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). 13'-Hydroxy-r-tocotrienol is a precursor in dehydrogenation to form 13'-carboxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   11.0973  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -11.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -10.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -12.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -13.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -13.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7479  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -14.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8085  -16.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2198  -17.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3948  -17.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2192  -18.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9331  -18.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6482  -18.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3616  -18.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0768  -18.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7907  -18.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0774  -17.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7926  -17.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3641  -17.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3654  -16.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6495  -17.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9350  -17.2291    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  5  2  0  0  0  0
  3  4  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
  8  9  1  0  0  0  0
  8 10  2  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
 13 14  1  0  0  0  0
 13 15  2  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
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 31  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 30  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 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
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END


  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   11.0973  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -11.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -11.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -10.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599  -12.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -13.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -13.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354  -14.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7479  -14.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -14.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5729  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104  -15.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2222  -16.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8085  -16.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2198  -17.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3948  -17.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2192  -18.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9331  -18.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6482  -18.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3616  -18.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0768  -18.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7907  -18.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0774  -17.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7926  -17.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3641  -17.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3654  -16.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6495  -17.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9350  -17.2291    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  5  2  0  0  0  0
  3  4  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
  8  9  1  0  0  0  0
  8 10  2  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
 13 14  1  0  0  0  0
 13 15  2  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
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 31  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 30  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 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
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h10,13-14,18,29-30H,7-9,11-12,15-17,19H2,1-6H3/b20-10+,21-14+,22-13+/t28-/m0/s1

> <INCHI_KEY>
BUWYMGRHXZROTQ-XYSSNJNPSA-N

> <FORMULA>
C28H42O3

> <MOLECULAR_WEIGHT>
426.6313

> <EXACT_MASS>
426.31339521

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53312232180242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
6.85

> <JCHEM_LOGP>
7.496786270000002

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.64401762943001

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.470422022977031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068162575387

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
134.65759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.715 -22.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.175 -22.260   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.405 -20.928   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      19.175 -19.593   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      18.405 -23.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.175 -24.928   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.715 -24.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.485 -26.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.715 -27.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.026 -26.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.796 -27.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.336 -27.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.106 -28.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.336 -30.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.646 -28.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.415 -30.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.643 -31.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.410 -32.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.870 -32.927   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.409 -34.469   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.742 -35.241   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.077 -34.472   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.408 -35.244   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.743 -34.475   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      35.076 -35.248   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      33.744 -32.936   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.080 -32.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.413 -32.163   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.415 -30.625   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      31.079 -32.932   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      29.745 -32.161   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   22   28   31                                                  
CONECT   31   18   30                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
13'-Hydroxy-g-tocotrienol	Generator
13'-Hydroxy-γ-tocotrienol	Generator
13OHgammaTE	HMDB

Chemical Formula

C₂₈H₄₂O₃

Average Mass

426.6313 Da

Monoisotopic Mass

426.31340 Da

IUPAC Name

(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2S)-2-[(3E,7E,11E)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CC\C(C)=C\CC\C(C)=C\CC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

InChI Identifier

InChI=1S/C28H42O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h10,13-14,18,29-30H,7-9,11-12,15-17,19H2,1-6H3/b20-10+,21-14+,22-13+/t28-/m0/s1

InChI Key

BUWYMGRHXZROTQ-XYSSNJNPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Tocotrienol
Diterpenoid
Long chain fatty alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
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	6.85	ALOGPS
logP	7.5	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.66 m³·mol⁻¹	ChemAxon
Polarizability	53.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012562

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029128

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481468

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 13'-Hydroxy-gamma-tocotrienol (NP0339046)

MOL for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

3D MOL for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

3D SDF for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

3D-SDF for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

PDB for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

3D PDB for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

SMILES for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

INCHI for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

Structure for NP0339046 (13'-Hydroxy-gamma-tocotrienol)

3D Structure for NP0339046 (13'-Hydroxy-gamma-tocotrienol)