NP-MRD: Showing NP-Card for 13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid (NP0169929)

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Record Information

Version

2.0

Created at

2022-09-03 05:58:41 UTC

Updated at

2022-09-03 05:58:41 UTC

NP-MRD ID

NP0169929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid

Description

13-(6-Hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain. 13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid is found in Garcinia kola. 13-(6-Hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503102D          

 31 32  0  0  0  0            999 V2000
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   -3.6641    2.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2873    0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004181503102D          

 31 32  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0169929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(O)=O)=CCCC(C)=CCCC1(C)CCC2=CC(O)=CC(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)

> <INCHI_KEY>
QOFWRHWADNWKSU-UHFFFAOYSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.61959763945954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
6.42

> <JCHEM_LOGP>
7.455828636333333

> <ALOGPS_LOGS>
-5.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.141678346417196

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.071153990985888

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852271747433423

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
129.5589

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.81e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -5.850   5.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.840   4.548   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.313   3.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.796   2.834   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.270   1.387   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.753   1.119   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.763   2.299   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.356   4.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.883   6.263   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.399   6.530   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.926   7.977   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.936   9.157   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.443   8.245   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -12.970   9.692   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -13.433   7.065   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21   10                                                       
CONECT   23    6                                                            
CONECT   24    2   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
13-(6-Hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoate	Generator

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid

Traditional Name

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(O)=O)=CCCC(C)=CCCC1(C)CCC2=CC(O)=CC(C)=C2O1

InChI Identifier

InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)

InChI Key

QOFWRHWADNWKSU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia kola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Tocotrienol
Diterpenoid
Long-chain fatty acid
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Heterocyclic fatty acid
Phenol
Methyl-branched fatty acid
Branched fatty acid
Alkyl aryl ether
Unsaturated fatty acid
Benzenoid
Fatty acyl
Fatty acid
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
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	6.42	ALOGPS
logP	7.46	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	5.07	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	10	ChemAxon
Refractivity	129.56 m³·mol⁻¹	ChemAxon
Polarizability	50.62 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

74493487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid (NP0169929)

MOL for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

3D MOL for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

3D SDF for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

3D-SDF for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

PDB for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

3D PDB for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

SMILES for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

INCHI for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

Structure for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)

3D Structure for NP0169929 (13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienoic acid)