NP-MRD: Showing NP-Card for 6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran (NP0031322)

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Record Information

Version

2.0

Created at

2021-06-19 22:26:09 UTC

Updated at

2021-06-29 23:59:49 UTC

NP-MRD ID

NP0031322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran

Provided By

JEOL Database JEOL Logo

Description

2,2,8-Trimethyl-2H-chromen-6-ol belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran is found in Gunnera perpensa. 6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran was first documented in 2005 (Drewes, S. E., et al.). Based on a literature review very few articles have been published on 2,2,8-trimethyl-2H-chromen-6-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100263D          

 28 29  0  0  0  0            999 V2000
   -0.4564    0.8149   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980   -0.1669   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.2923    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.6219    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324   -0.2095    1.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9979   -1.9901    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -2.4625   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -1.5518   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.9361   -1.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -3.3389   -1.8657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7778   -3.5657   -3.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -3.5956   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -4.2937   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8378   -3.8920   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180    0.6900   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5120    0.6686   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958    1.8486   -1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    1.3596    0.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377    0.7615    1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -2.6785    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567   -3.3442   -3.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.8917   -3.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -4.5961   -3.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321   -3.3959   -0.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -4.6274   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -2.9222   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -5.3581   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575   -4.5943    0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  6  1  0  0  0  0
  6  4  2  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
 10 11  1  0  0  0  0
  2  8  1  0  0  0  0
 10 12  1  0  0  0  0
  3 18  1  0  0  0  0
  6 20  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
  5 19  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
 11 21  1  0  0  0  0
 11 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 12 26  1  0  0  0  0
M  END


  Mrv1652306202100263D          

 28 29  0  0  0  0            999 V2000
   -0.4564    0.8149   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980   -0.1669   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.2923    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682   -0.6219    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324   -0.2095    1.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9979   -1.9901    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -2.4625   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -1.5518   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.9361   -1.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -3.3389   -1.8657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7778   -3.5657   -3.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -3.5956   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -4.2937   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8378   -3.8920   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180    0.6900   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5120    0.6686   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958    1.8486   -1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    1.3596    0.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377    0.7615    1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -2.6785    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567   -3.3442   -3.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.8917   -3.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -4.5961   -3.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321   -3.3959   -0.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -4.6274   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -2.9222   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -5.3581   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575   -4.5943    0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  6  1  0  0  0  0
  6  4  2  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
 10 11  1  0  0  0  0
  2  8  1  0  0  0  0
 10 12  1  0  0  0  0
  3 18  1  0  0  0  0
  6 20  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
  5 19  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
 11 21  1  0  0  0  0
 11 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 12 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(OC(C([H])=C2[H])(C([H])([H])[H])C([H])([H])[H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O2/c1-8-6-10(13)7-9-4-5-12(2,3)14-11(8)9/h4-7,13H,1-3H3

> <INCHI_KEY>
UGRCUEXFQNLHMI-UHFFFAOYSA-N

> <FORMULA>
C12H14O2

> <MOLECULAR_WEIGHT>
190.242

> <EXACT_MASS>
190.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.338869126468996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,8-trimethyl-2H-chromen-6-ol

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.0837252856666666

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.972723647669952

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8862793859670965

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
57.4735

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,8-trimethylchromen-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.456   0.815  -1.325  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.398  -0.167  -0.573  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.380   0.292   0.316  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.168  -0.622   1.009  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.132  -0.210   1.881  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.998  -1.990   0.834  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.023  -2.462  -0.049  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.224  -1.552  -0.751  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.750  -1.936  -1.632  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.985  -3.339  -1.866  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.778  -3.566  -3.368  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.452  -3.596  -1.503  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.107  -4.294  -1.092  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.838  -3.892  -0.238  0.00  0.00           C+0
HETATM   15  H   UNK     0      -0.318   0.690  -2.403  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.512   0.669  -1.073  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.196   1.849  -1.074  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.521   1.360   0.459  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.138   0.762   1.902  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.629  -2.679   1.389  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.257  -3.344  -3.657  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.412  -2.892  -3.956  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.004  -4.596  -3.663  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.632  -3.396  -0.440  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.754  -4.627  -1.714  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.116  -2.922  -2.058  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.261  -5.358  -1.248  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.458  -4.594   0.307  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3    8                                                  
CONECT    3    4    2   18                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   19                                                       
CONECT    6    7    4   20                                                  
CONECT    7    6   14    8                                                  
CONECT    8    9    7    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   13   11   12                                             
CONECT   11   10   21   22   23                                             
CONECT   12   10   24   25   26                                             
CONECT   13   10   14   27                                                  
CONECT   14    7   13   28                                                  
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21   11                                                            
CONECT   22   11                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   12                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₂

Average Mass

190.2420 Da

Monoisotopic Mass

190.09938 Da

IUPAC Name

2,2,8-trimethyl-2H-chromen-6-ol

Traditional Name

2,2,8-trimethylchromen-6-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(OC(C([H])=C2[H])(C([H])([H])[H])C([H])([H])[H])C(=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C12H14O2/c1-8-6-10(13)7-9-4-5-12(2,3)14-11(8)9/h4-7,13H,1-3H3

InChI Key

UGRCUEXFQNLHMI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gunnera perpensa	JEOL database	Drewes, S. E., et al, Phytochemistry 66, 1812 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxacycle
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	3.03	ALOGPS
logP	3.08	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.97	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	0	ChemAxon
Refractivity	57.47 m³·mol⁻¹	ChemAxon
Polarizability	21.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10217515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14761705

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Drewes, S. E., et al. (2005). Drewes, S. E., et al, Phytochemistry 66, 1812 (2005) . Phytochem..

Showing NP-Card for 6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran (NP0031322)

MOL for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

3D MOL for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

3D SDF for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

3D-SDF for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

PDB for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

3D PDB for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

SMILES for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

INCHI for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

Structure for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)

3D Structure for NP0031322 (6-hydroxy-8-methyl-2,2-dimethyl-2H-benzopyran)