NP-MRD: Showing NP-Card for 2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol (NP0214742)

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Record Information

Version

2.0

Created at

2022-09-05 14:07:58 UTC

Updated at

2022-09-05 14:07:58 UTC

NP-MRD ID

NP0214742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol

Description

2,8-Dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol 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. 2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol is found in Bixa orellana, Cinnamosma fragrans, Cinnamosma madagascariensis, Cratoxylum cochinchinense, Cystophora monilifera, Garcinia kola, Kielmeyera coriacea and Pleodendron costaricense. 2,8-Dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500542D          

 29 30  0  0  0  0            999 V2000
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   -5.8533    4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3819    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2873    0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -0.1757    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


  Mrv1533004171500542D          

 29 30  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0214742

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3

> <INCHI_KEY>
ODADKLYLWWCHNB-UHFFFAOYSA-N

> <FORMULA>
C27H40O2

> <MOLECULAR_WEIGHT>
396.615

> <EXACT_MASS>
396.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.59841537205722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
8.264136037333332

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141674654384879

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85227174738162

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
127.84169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0     -12.443   8.245   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.926   7.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.399   6.530   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.883   6.263   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.356   4.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.840   4.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.313   3.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.796   2.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.270   1.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.753   1.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.763   2.299   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.850   5.728   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.936   9.157   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   14                                                       
CONECT   27   10                                                            
CONECT   28    6                                                            
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₂

Average Mass

396.6150 Da

Monoisotopic Mass

396.30283 Da

IUPAC Name

2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3

InChI Key

ODADKLYLWWCHNB-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
Bixa orellana	LOTUS Database	35616633
Cinnamosma fragrans	LOTUS Database	35616633
Cinnamosma madagascariensis	LOTUS Database	35616633
Cratoxylum cochinchinense	LOTUS Database	35616633
Cystophora monilifera	LOTUS Database	35616633
Garcinia kola	LOTUS Database	35616633
Kielmeyera coriacea	LOTUS Database	35616633
Pleodendron costaricense	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
1-benzopyran
Benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	7.71	ALOGPS
logP	8.26	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	49.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

53394607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol (NP0214742)

MOL for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

3D MOL for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

3D SDF for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

3D-SDF for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

PDB for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

3D PDB for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

SMILES for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

INCHI for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

Structure for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)

3D Structure for NP0214742 (2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-1-benzopyran-6-ol)