NP-MRD: Showing NP-Card for 9'-Carboxy-alpha-tocotrienol (NP0339104)

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Record Information

Version

2.0

Created at

2024-09-11 19:42:13 UTC

Updated at

2024-09-11 19:42:13 UTC

NP-MRD ID

NP0339104

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9'-Carboxy-alpha-tocotrienol

Description

9'-Carboxy-alpha-tocotrienol, also known as alpha-cdmoenhc, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 9'-Carboxy-alpha-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). 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 members of the vitamin E family. 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. 9'-Carboxy-alpha-tocotrienol is a dehydrogenation carboxylate product of 9'-hydroxy-a-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 28 29  0  0  1  0            999 V2000
   11.9326  -12.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -12.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -12.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -11.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -10.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -10.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9326  -10.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952   -9.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076   -8.6016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8703   -9.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -13.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -14.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -15.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -15.7457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2827  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8222  -16.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5367  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -16.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -17.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9652  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6797  -16.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9652  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6797  -15.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -15.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -14.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5367  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8222  -15.3332    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 11  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
  8 10  2  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
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  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
M  END


  Mrv1652303102016462D          

 28 29  0  0  1  0            999 V2000
   11.9326  -12.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -12.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -12.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -11.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -10.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -10.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9326  -10.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952   -9.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076   -8.6016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8703   -9.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -13.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -14.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6952  -15.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -15.7457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2827  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1076  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8222  -16.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5367  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -16.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -17.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9652  -16.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6797  -16.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9652  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6797  -15.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -15.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2512  -14.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5367  -15.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8222  -15.3332    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 11  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
  8 10  2  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
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  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
M  END
> <DATABASE_ID>
NP0339104

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h10-11,25H,7-9,12-14H2,1-6H3,(H,26,27)/b15-10+,16-11+/t24-/m1/s1

> <INCHI_KEY>
MEZYOZBFEXYIKB-ASKDMKCJSA-N

> <FORMULA>
C24H34O4

> <MOLECULAR_WEIGHT>
386.5244

> <EXACT_MASS>
386.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.219224660088486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
6.822957140000001

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.80214075993822

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.011796454196202

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8526692502020135

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
115.83869999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.65e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      22.274 -24.058   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.734 -24.058   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.964 -22.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.734 -21.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.964 -20.056   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.734 -18.723   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.274 -18.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.964 -17.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      20.734 -16.056   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      18.425 -17.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      19.964 -25.392   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.734 -26.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.964 -28.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.734 -29.392   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.194 -29.392   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.734 -30.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.068 -31.702   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.402 -30.932   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.736 -31.702   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.736 -33.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.068 -30.932   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      27.402 -31.702   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      26.068 -29.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.402 -28.622   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.736 -28.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.736 -27.082   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.402 -29.392   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      22.068 -28.622   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   28                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   18   25   28                                                  
CONECT   28   14   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
9'-Carboxy-a-tocotrienol	Generator
9'-Carboxy-α-tocotrienol	Generator
alpha-CDMOenHC	HMDB
(2E,6E)-9-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoate	Generator

Chemical Formula

C₂₄H₃₄O₄

Average Mass

386.5244 Da

Monoisotopic Mass

386.24571 Da

IUPAC Name

(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

Traditional Name

(2E,6E)-9-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H34O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h10-11,25H,7-9,12-14H2,1-6H3,(H,26,27)/b15-10+,16-11+/t24-/m1/s1

InChI Key

MEZYOZBFEXYIKB-ASKDMKCJSA-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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	5.36	ALOGPS
logP	6.82	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.01	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	7	ChemAxon
Refractivity	115.84 m³·mol⁻¹	ChemAxon
Polarizability	46.22 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

HMDB0012867

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029191

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

53481535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9'-Carboxy-alpha-tocotrienol (NP0339104)

MOL for NP0339104 (9'-Carboxy-alpha-tocotrienol)

3D MOL for NP0339104 (9'-Carboxy-alpha-tocotrienol)

3D SDF for NP0339104 (9'-Carboxy-alpha-tocotrienol)

3D-SDF for NP0339104 (9'-Carboxy-alpha-tocotrienol)

PDB for NP0339104 (9'-Carboxy-alpha-tocotrienol)

3D PDB for NP0339104 (9'-Carboxy-alpha-tocotrienol)

SMILES for NP0339104 (9'-Carboxy-alpha-tocotrienol)

INCHI for NP0339104 (9'-Carboxy-alpha-tocotrienol)

Structure for NP0339104 (9'-Carboxy-alpha-tocotrienol)

3D Structure for NP0339104 (9'-Carboxy-alpha-tocotrienol)