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Showing NP-Card for 11'-Carboxy-alpha-chromanol (NP0339026)

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Record Information
Version2.0
Created at2024-09-11 19:19:07 UTC
Updated at2024-09-11 19:19:08 UTC
NP-MRD IDNP0339026
Secondary Accession NumbersNone
Natural Product Identification
Common Name11'-Carboxy-alpha-chromanol
Description11'-Carboxy-alpha-chromanol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 11'-Carboxy-alpha-chromanol is an extremely weak basic (essentially neutral) compound (based on its pKa). In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339026 (11'-Carboxy-alpha-chromanol)


  Mrv0541 02251208062D          

 30 31  0  0  1  0            999 V2000
   12.3086  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -12.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -11.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -10.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520   -9.9796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1665   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8810   -9.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3099   -9.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -8.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -13.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -13.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -14.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -14.9297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7376  -15.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1646  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 29  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
Download

3D MOL for NP0339026 (11'-Carboxy-alpha-chromanol)

Download
3D SDF for NP0339026 (11'-Carboxy-alpha-chromanol)

  Mrv0541 02251208062D          

 30 31  0  0  1  0            999 V2000
   12.3086  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -12.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376  -12.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -11.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -10.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520   -9.9796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7376   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1665   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8810   -9.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -9.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3099   -9.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -8.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0231  -13.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -13.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376  -14.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4520  -14.9297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7376  -15.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -14.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -14.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1646  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9270  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -16.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6895  -15.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8645  -15.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 29  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h17-18,29H,7-16H2,1-6H3,(H,27,28)/t17-,18+,26+/m0/s1

> <INCHI_KEY>
FKTCHXAVPYGOSM-CUAXAMRHSA-N

> <FORMULA>
C26H42O4

> <MOLECULAR_WEIGHT>
418.6093

> <EXACT_MASS>
418.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.086101231628064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <ALOGPS_LOGP>
6.43

> <JCHEM_LOGP>
8.011319068666667

> <ALOGPS_LOGS>
-6.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178884212683

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.044405650385452

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8526149018312505

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
123.28889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339026 (11'-Carboxy-alpha-chromanol)
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PDB for NP0339026 (11'-Carboxy-alpha-chromanol)
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      22.976 -22.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.310 -23.249   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.644 -22.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.644 -20.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.977 -20.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.977 -18.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.644 -17.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.311 -17.859   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.645 -18.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.978 -17.859   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      32.312 -18.629   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      30.978 -16.319   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.310 -24.789   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.644 -25.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.644 -27.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.977 -27.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.644 -28.639   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.747 -26.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.287 -26.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.057 -27.869   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.597 -27.869   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.367 -26.535   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.367 -29.203   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      33.907 -29.203   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      31.597 -30.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.367 -31.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.057 -30.536   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.287 -31.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.287 -29.203   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      27.747 -29.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   20   27   30                                                  
CONECT   30   16   29                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

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3D PDB for NP0339026 (11'-Carboxy-alpha-chromanol)
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SMILES for NP0339026 (11'-Carboxy-alpha-chromanol)
C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
Download
INCHI for NP0339026 (11'-Carboxy-alpha-chromanol)
InChI=1S/C26H42O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h17-18,29H,7-16H2,1-6H3,(H,27,28)/t17-,18+,26+/m0/s1
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View in JSmol
Synonyms
ValueSource
11'-Carboxy-alpha-tocopherolHMDB
(4R,8S)-11-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoateGenerator
Chemical FormulaC26H42O4
Average Mass418.6093 Da
Monoisotopic Mass418.30831 Da
IUPAC Name(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid
Traditional Name(4R,8S)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundecanoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](CCC[C@@H](C)CCC(O)=O)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI Identifier
InChI=1S/C26H42O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h17-18,29H,7-16H2,1-6H3,(H,27,28)/t17-,18+,26+/m0/s1
InChI KeyFKTCHXAVPYGOSM-CUAXAMRHSA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Long-chain fatty acid
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Alkyl aryl ether
    • 

  • Branched fatty acid
    • 

  • Heterocyclic fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Benzenoid
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP6.43ALOGPS
logP8.01ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)5.04ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity123.29 m³·mol⁻¹ChemAxon
Polarizability51.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012515  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029108  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481451  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available