NP-MRD: Showing NP-Card for 13'-Hydroxy-alpha-tocopherol (NP0339043)

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Record Information

Version

2.0

Created at

2024-09-11 19:24:53 UTC

Updated at

2024-09-11 19:24:53 UTC

NP-MRD ID

NP0339043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13'-Hydroxy-alpha-tocopherol

Description

13'-Hydroxy-alpha-tocopherol, also known as 13-OH-a-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-alpha-tocopherol is an extremely weak basic (essentially neutral) compound (based on its pKa). The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. These remnants are taken up by the liver.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 32 33  0  0  1  0            999 V2000
   13.1637  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1637  -11.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9887  -11.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9262  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5137  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -13.9718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4512  -13.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -14.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -15.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -16.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -16.8298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4512  -16.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -17.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5137  -17.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9262  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -18.2587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3387  -18.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4656  -17.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1801  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -17.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -16.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6091  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3235  -17.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6091  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3235  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -19.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1801  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4656  -18.6712    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  6  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  6  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 32  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 31  2  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
 25 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
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END


  Mrv0541 02251208062D          

 32 33  0  0  1  0            999 V2000
   13.1637  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1637  -11.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9887  -11.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9262  -12.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5137  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -13.9718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4512  -13.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -14.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -15.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -16.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2762  -16.8298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4512  -16.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6887  -17.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5137  -17.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9262  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -18.2587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3387  -18.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7512  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4656  -17.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1801  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -17.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -16.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6091  -17.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3235  -17.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6091  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3235  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8946  -19.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1801  -18.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4656  -18.6712    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  6  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  6  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 32  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 31  2  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
 25 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
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339043

> <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)=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1

> <INCHI_KEY>
URYLCCKXLNXSRS-XIRVVSDESA-N

> <FORMULA>
C29H50O3

> <MOLECULAR_WEIGHT>
446.7055

> <EXACT_MASS>
446.375995466

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.32392379126493

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
8.07

> <JCHEM_LOGP>
9.148992373333334

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.418322874869105

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.802178125614303

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7406898159721043

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
137.22579999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-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      24.572 -24.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.802 -23.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.572 -22.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.112 -22.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.262 -23.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.492 -24.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.952 -24.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.182 -26.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.642 -26.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.952 -27.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.182 -28.748   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.952 -30.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.182 -31.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.642 -31.416   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.952 -32.749   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.492 -32.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.262 -34.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.802 -34.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.032 -35.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.802 -32.543   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.136 -31.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.470 -32.543   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.803 -31.773   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.803 -30.233   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.137 -32.543   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      30.471 -31.773   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      29.137 -34.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.471 -34.853   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.803 -34.853   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.803 -36.393   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.470 -34.083   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.136 -34.853   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   32                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   22   29   32                                                  
CONECT   32   18   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
13-OH-alpha-Tocopherol	ChEBI
13-OH-a-Tocopherol	Generator
13-OH-Α-tocopherol	Generator
13'-Hydroxy-a-tocopherol	Generator
13'-Hydroxy-α-tocopherol	Generator
13'-Hydroxy-alpha-tocopherol	ChEBI
13-Hydroxy-a-tocopherol	Generator
13-Hydroxy-α-tocopherol	Generator

Chemical Formula

C₂₉H₅₀O₃

Average Mass

446.7055 Da

Monoisotopic Mass

446.37600 Da

IUPAC Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not 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)=C2C

InChI Identifier

InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1

InChI Key

URYLCCKXLNXSRS-XIRVVSDESA-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 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
Diterpenoid
Long chain fatty alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
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

phenols (CHEBI:84962 )
primary alcohol (CHEBI:84962 )
chromanol (CHEBI:84962 )

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	8.07	ALOGPS
logP	9.15	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-1.7	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	13	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	57.32 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

HMDB0012559

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029125

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-11960

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481465

PDB ID

Not Available

ChEBI ID

84962

Good Scents ID

Not Available

References

General References

Showing NP-Card for 13'-Hydroxy-alpha-tocopherol (NP0339043)

MOL for NP0339043 (13'-Hydroxy-alpha-tocopherol)

3D MOL for NP0339043 (13'-Hydroxy-alpha-tocopherol)

3D SDF for NP0339043 (13'-Hydroxy-alpha-tocopherol)

3D-SDF for NP0339043 (13'-Hydroxy-alpha-tocopherol)

PDB for NP0339043 (13'-Hydroxy-alpha-tocopherol)

3D PDB for NP0339043 (13'-Hydroxy-alpha-tocopherol)

SMILES for NP0339043 (13'-Hydroxy-alpha-tocopherol)

INCHI for NP0339043 (13'-Hydroxy-alpha-tocopherol)

Structure for NP0339043 (13'-Hydroxy-alpha-tocopherol)

3D Structure for NP0339043 (13'-Hydroxy-alpha-tocopherol)