NP-MRD: Showing NP-Card for 11'-Carboxy-alpha-tocotrienol (NP0339027)

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Record Information

Version

2.0

Created at

2024-09-11 19:19:30 UTC

Updated at

2024-09-11 19:19:30 UTC

NP-MRD ID

NP0339027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11'-Carboxy-alpha-tocotrienol

Description

11'-Carboxy-alpha-tocotrienol, also known as alpha-CDMD(en)(,2)HC, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 11'-Carboxy-alpha-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). While the majority of research on vitamin E has focused on alpha-tocopherol, studies into tocotrienols account for less than 1% of all research into vitamin E. Tocotrienols are members of the vitamin E family. An essential nutrient for the body, vitamin E is made up of four tocopherols (alpha, beta, gamma, delta) and four tocotrienols (alpha, beta, gamma, delta). Tocotrienols are natural compounds found in select vegetable oils, wheat germ, barley, saw palmetto, and certain types of nuts and grains. This variant of vitamin E only occur at very low levels in nature.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 30 31  0  0  1  0            999 V2000
   14.7655  -12.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -12.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -11.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -10.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -9.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7655   -9.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281   -8.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -8.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281   -7.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -6.8349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7032   -7.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -13.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -13.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -14.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -15.4081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1156  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6551  -16.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3697  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -16.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -17.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7981  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5127  -16.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7981  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5127  -14.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -14.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -14.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3697  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6551  -14.9956    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 13  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  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  6  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


  Mrv0541 02251208062D          

 30 31  0  0  1  0            999 V2000
   14.7655  -12.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -12.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -11.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -10.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -9.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7655   -9.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281   -8.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -8.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281   -7.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -6.8349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7032   -7.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -13.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -13.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281  -14.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -15.4081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1156  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9406  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6551  -16.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3697  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -16.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -17.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7981  -16.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5127  -16.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7981  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5127  -14.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -14.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -14.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3697  -15.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6551  -14.9956    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 13  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  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  6  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>
NP0339027

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O4/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/h10-11,29H,7-9,12-16H2,1-6H3,(H,27,28)/b17-11+,18-10+/t26-/m1/s1

> <INCHI_KEY>
LAVCYAUSHCEKED-KYVGBUAPSA-N

> <FORMULA>
C26H38O4

> <MOLECULAR_WEIGHT>
414.5775

> <EXACT_MASS>
414.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.3782444897677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
7.200160106

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.80214063760481

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9288702970524545

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852669250214899

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
124.98889999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.95e-04 g/l

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

> <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      27.562 -23.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.022 -23.428   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.252 -22.094   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.022 -20.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.252 -19.426   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.022 -18.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.562 -18.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.252 -16.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.022 -15.426   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.252 -14.092   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      26.022 -12.758   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      23.713 -14.092   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      25.252 -24.762   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.022 -26.094   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.252 -27.428   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.022 -28.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.482 -28.762   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.022 -30.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.356 -31.072   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.690 -30.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.024 -31.072   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.024 -32.611   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.356 -30.302   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      32.690 -31.072   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      31.356 -28.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.690 -27.992   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.024 -27.992   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.024 -26.452   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.690 -28.762   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      27.356 -27.992   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

View in JSmol

Synonyms

Value	Source
11'-Carboxy-a-tocotrienol	Generator
11'-Carboxy-α-tocotrienol	Generator
alpha-CDMD(En)(,2)HC	HMDB
alpha-CDMD(En)(2)HC	HMDB
(4E,8E)-11-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoate	Generator

Chemical Formula

C₂₆H₃₈O₄

Average Mass

414.5775 Da

Monoisotopic Mass

414.27701 Da

IUPAC Name

(4E,8E)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid

Traditional Name

(4E,8E)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(CC\C=C(/C)CCC(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

InChI Identifier

InChI=1S/C26H38O4/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/h10-11,29H,7-9,12-16H2,1-6H3,(H,27,28)/b17-11+,18-10+/t26-/m1/s1

InChI Key

LAVCYAUSHCEKED-KYVGBUAPSA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

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
Unsaturated fatty acid
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 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	5.53	ALOGPS
logP	7.2	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.99 m³·mol⁻¹	ChemAxon
Polarizability	50.38 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

HMDB0012516

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029109

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

53481452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11'-Carboxy-alpha-tocotrienol (NP0339027)

MOL for NP0339027 (11'-Carboxy-alpha-tocotrienol)

3D MOL for NP0339027 (11'-Carboxy-alpha-tocotrienol)

3D SDF for NP0339027 (11'-Carboxy-alpha-tocotrienol)

3D-SDF for NP0339027 (11'-Carboxy-alpha-tocotrienol)

PDB for NP0339027 (11'-Carboxy-alpha-tocotrienol)

3D PDB for NP0339027 (11'-Carboxy-alpha-tocotrienol)

SMILES for NP0339027 (11'-Carboxy-alpha-tocotrienol)

INCHI for NP0339027 (11'-Carboxy-alpha-tocotrienol)

Structure for NP0339027 (11'-Carboxy-alpha-tocotrienol)

3D Structure for NP0339027 (11'-Carboxy-alpha-tocotrienol)