NP-MRD: Showing NP-Card for 7'-Carboxy-alpha-tocotrienol (NP0339099)

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Record Information

Version

2.0

Created at

2024-09-11 19:40:36 UTC

Updated at

2024-09-11 19:40:36 UTC

NP-MRD ID

NP0339099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7'-Carboxy-alpha-tocotrienol

Description

7'-Carboxy-alpha-tocotrienol, also known as alpha-cmhenhc, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 7'-Carboxy-alpha-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). This variant of vitamin E only occur at very low levels in nature. 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. 7'-Carboxy-alpha-tocotrienol is a dehydrogenation carboxylate product of 7'-hydroxy-a-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 25 26  0  0  1  0            999 V2000
   12.0022  -11.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772  -11.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648  -10.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772   -9.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648   -9.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772   -8.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9399   -9.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648  -11.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772  -12.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648  -13.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772  -14.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3523  -14.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1772  -14.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8918  -15.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6063  -14.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3208  -15.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3208  -16.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0347  -14.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7492  -15.3727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0347  -14.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7492  -13.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3208  -13.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3208  -12.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6063  -14.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8918  -13.7228    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  8  2  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
  5  7  2  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
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 11 25  1  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
 15 24  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339099

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-13(8-9-18(22)23)7-6-11-21(5)12-10-17-16(4)19(24)14(2)15(3)20(17)25-21/h7,24H,6,8-12H2,1-5H3,(H,22,23)/b13-7+/t21-/m1/s1

> <INCHI_KEY>
UZOSSXSASNQFOI-FAKWYAOSSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.4605

> <EXACT_MASS>
346.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.602476446638136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
5.5404458309999995

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802140327039965

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.597145997895954

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85266925033983

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
101.18629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-7-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4-methylhept-4-enoic 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      22.404 -21.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.864 -21.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.094 -19.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.864 -18.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.094 -17.051   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      20.864 -15.717   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.554 -17.051   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      20.094 -22.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.864 -23.718   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.094 -25.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.864 -26.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.324 -26.386   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.864 -27.926   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.198 -28.696   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.532 -27.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.865 -28.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.865 -30.236   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.198 -27.926   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      27.532 -28.696   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      26.198 -26.386   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.532 -25.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.865 -25.616   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.865 -24.076   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.532 -26.386   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      22.198 -25.616   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   15   22   25                                                  
CONECT   25   11   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₁H₃₀O₄

Average Mass

346.4605 Da

Monoisotopic Mass

346.21441 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H30O4/c1-13(8-9-18(22)23)7-6-11-21(5)12-10-17-16(4)19(24)14(2)15(3)20(17)25-21/h7,24H,6,8-12H2,1-5H3,(H,22,23)/b13-7+/t21-/m1/s1

InChI Key

UZOSSXSASNQFOI-FAKWYAOSSA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Benzenoid
Monocarboxylic acid or derivatives
Oxacycle
Ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	4.56	ALOGPS
logP	5.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.6	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	6	ChemAxon
Refractivity	101.19 m³·mol⁻¹	ChemAxon
Polarizability	40.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012849

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029186

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

53481530

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7'-Carboxy-alpha-tocotrienol (NP0339099)

MOL for NP0339099 (7'-Carboxy-alpha-tocotrienol)

3D MOL for NP0339099 (7'-Carboxy-alpha-tocotrienol)

3D SDF for NP0339099 (7'-Carboxy-alpha-tocotrienol)

3D-SDF for NP0339099 (7'-Carboxy-alpha-tocotrienol)

PDB for NP0339099 (7'-Carboxy-alpha-tocotrienol)

3D PDB for NP0339099 (7'-Carboxy-alpha-tocotrienol)

SMILES for NP0339099 (7'-Carboxy-alpha-tocotrienol)

INCHI for NP0339099 (7'-Carboxy-alpha-tocotrienol)

Structure for NP0339099 (7'-Carboxy-alpha-tocotrienol)

3D Structure for NP0339099 (7'-Carboxy-alpha-tocotrienol)