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Showing NP-Card for 13'-Hydroxy-gamma-tocopherol (NP0339045)

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Record Information
Version2.0
Created at2024-09-11 19:25:24 UTC
Updated at2024-09-11 19:25:24 UTC
NP-MRD IDNP0339045
Secondary Accession NumbersNone
Natural Product Identification
Common Name13'-Hydroxy-gamma-tocopherol
Description13'-Hydroxy-gamma-tocopherol, also known as 13'-OH-tocopherol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. 13'-Hydroxy-gamma-tocopherol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339045 (13'-Hydroxy-gamma-tocopherol)


  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   13.4421  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4421  -10.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2671  -10.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -13.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -13.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -13.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -14.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -15.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -15.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -15.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -17.2881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6171  -18.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -16.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -17.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -17.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -18.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -17.7006    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  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
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 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 18 31  1  0  0  0  0
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 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
Download

3D MOL for NP0339045 (13'-Hydroxy-gamma-tocopherol)

Download
3D SDF for NP0339045 (13'-Hydroxy-gamma-tocopherol)

  Mrv0541 02251208072D          

 31 32  0  0  1  0            999 V2000
   13.4421  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4421  -10.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2671  -10.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -11.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -13.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -13.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -13.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -14.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -15.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5546  -15.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7296  -15.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9671  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2046  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -17.2881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6171  -18.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0296  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -16.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -16.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -16.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -17.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -17.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1730  -18.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4585  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7441  -17.7006    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  1  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  1  0  0  0
  8 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
 13 14  1  1  0  0  0
 13 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
 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>
NP0339045

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O3/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/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1

> <INCHI_KEY>
QNBPVJMQPAQXML-SLGTZZLGSA-N

> <FORMULA>
C28H48O3

> <MOLECULAR_WEIGHT>
432.6789

> <EXACT_MASS>
432.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.091136926254684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(4S,8R)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.05

> <JCHEM_LOGP>
8.635570984000001

> <ALOGPS_LOGS>
-7.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.418322874869105

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.470460494567556

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7406896624370471

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
132.18459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4S,8R)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339045 (13'-Hydroxy-gamma-tocopherol)
Download
PDB for NP0339045 (13'-Hydroxy-gamma-tocopherol)
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      25.092 -22.935   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.322 -21.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.092 -20.268   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.632 -20.268   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.782 -21.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.012 -22.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.472 -22.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.702 -24.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.162 -24.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.472 -25.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.702 -26.936   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.472 -28.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.702 -29.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.162 -29.604   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.472 -30.937   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.012 -30.937   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.782 -32.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.322 -32.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.552 -33.605   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.322 -30.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.656 -29.961   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.989 -30.731   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.323 -29.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.657 -30.731   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.990 -29.961   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      29.657 -32.271   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.990 -33.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.323 -33.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.323 -34.581   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.989 -32.271   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      25.656 -33.041   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

Download
3D PDB for NP0339045 (13'-Hydroxy-gamma-tocopherol)
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SMILES for NP0339045 (13'-Hydroxy-gamma-tocopherol)
CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
Download
INCHI for NP0339045 (13'-Hydroxy-gamma-tocopherol)
InChI=1S/C28H48O3/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/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1
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View in JSmol
Synonyms
ValueSource
13'-Hydroxy-g-tocopherolGenerator
13'-Hydroxy-γ-tocopherolGenerator
13'-OH-TocopherolHMDB
Chemical FormulaC28H48O3
Average Mass432.6789 Da
Monoisotopic Mass432.36035 Da
IUPAC Name(2R)-2-[(4S,8R)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name(2R)-2-[(4S,8R)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol
CAS Registry NumberNot Available
SMILES
CC(CO)CCC[C@H](C)CCC[C@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
InChI Identifier
InChI=1S/C28H48O3/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/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1
InChI KeyQNBPVJMQPAQXML-SLGTZZLGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassQuinone and hydroquinone lipids  
Direct ParentTocopherols  
Alternative Parents
Substituents
  • Tocopherol
    • 

  • Diterpenoid
    • 

  • 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 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
logP8.05ALOGPS
logP8.64ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.18 m³·mol⁻¹ChemAxon
Polarizability55.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012561  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029127  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481467  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References