NP-MRD: Showing NP-Card for 6-Acetyl-2,2-dimethyl-2H-1-benzopyran (NP0046038)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:23 UTC

Updated at

2022-03-17 19:47:23 UTC

NP-MRD ID

NP0046038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Acetyl-2,2-dimethyl-2H-1-benzopyran

Description

6-Acetyl-2,2-dimethyl-2H-1-benzopyran 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-Acetyl-2,2-dimethyl-2H-1-benzopyran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-Acetyl-2,2-dimethyl-2H-1-benzopyran is found, on average, in the highest concentration within sunflowers. 6-Acetyl-2,2-dimethyl-2H-1-benzopyran has also been detected, but not quantified in, fats and oils. 6-Acetyl-2,2-dimethyl-2H-1-benzopyran is found in Ageratina adenophora, Ageratina conyzoides, Ageratina glechonophylla, Ageratum conyzoides, Arnica amplexicaulis, Arnica lanceolata, Arnica lessingii, Baccharis calvescens, Baccharis quitensis, Bejaranoa semistriata, Ageratina altissima, Helianthella quinquenervis, Helianthella uniflora, Helianthus annuus, Helianthus hirsutus, Hemizonia congesta, Leucoblepharis subsessilis, Madia sativa, Tithonia diversifolia, Trichogonia salviifolia, Vitex agnus-castus and Xanthium pungens. This could make 6-acetyl-2,2-dimethyl-2H-1-benzopyran a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305312D          

 15 16  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
  9  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=CC2=C(OC(C)(C)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O2/c1-9(14)10-4-5-12-11(8-10)6-7-13(2,3)15-12/h4-8H,1-3H3

> <INCHI_KEY>
ZAJTXVHECZCXLH-UHFFFAOYSA-N

> <FORMULA>
C13H14O2

> <MOLECULAR_WEIGHT>
202.2491

> <EXACT_MASS>
202.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.560481946080063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,2-dimethyl-2H-chromen-6-yl)ethan-1-one

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.4315167366666666

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.236806410998476

> <JCHEM_PKA_STRONGEST_BASIC>
-4.915994971033945

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.85420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,2-dimethylchromen-6-yl)ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.518   3.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.528   5.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   10   11                                                       
CONECT    9    1   10   14                                                  
CONECT   10    4    8    9                                                  
CONECT   11    6    8   12                                                  
CONECT   12    5   11   15                                                  
CONECT   13    2    3    7   15                                             
CONECT   14    9                                                            
CONECT   15   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
1-(2,2-Dimethyl-2H-1-benzopyran-6-yl)ethanone, 9ci	HMDB
1-(2,2-Dimethyl-2H-chromen-6-yl)ethanone	HMDB
1-(2,2-Dimethylchromen-6-yl)ethan-1-one	HMDB
6-Acetyl-2,2-dimethyl-3-chromene	HMDB
Demethoxyencecalin	HMDB
Desmethoxyencecalin	HMDB

Chemical Formula

C₁₃H₁₄O₂

Average Mass

202.2491 Da

Monoisotopic Mass

202.09938 Da

IUPAC Name

1-(2,2-dimethyl-2H-chromen-6-yl)ethan-1-one

Traditional Name

1-(2,2-dimethylchromen-6-yl)ethanone

CAS Registry Number

19013-07-1

SMILES

CC(=O)C1=CC2=C(OC(C)(C)C=C2)C=C1

InChI Identifier

InChI=1S/C13H14O2/c1-9(14)10-4-5-12-11(8-10)6-7-13(2,3)15-12/h4-8H,1-3H3

InChI Key

ZAJTXVHECZCXLH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ageratina adenophora	LOTUS Database	35616633
Ageratina conyzoides	Plant	KNApSAcK
Ageratina glechonophylla	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Arnica amplexicaulis	LOTUS Database	35616633
Arnica lanceolata	LOTUS Database	35616633
Arnica lessingii	LOTUS Database	35616633
Baccharis calvescens	LOTUS Database	35616633
Baccharis quitensis	LOTUS Database	35616633
Bejaranoa semistriata	LOTUS Database	35616633
Eupatorium rugosum	LOTUS Database	35616633
Helianthella quinquenervis	LOTUS Database	35616633
Helianthella uniflora	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus hirsutus	LOTUS Database	35616633
Hemizonia congesta	Plant	KNApSAcK
Leucoblepharis subsessilis	LOTUS Database	35616633
Madia sativa	LOTUS Database	35616633
Tithonia diversifolia	LOTUS Database	35616633
Trichogonia salviifolia	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Xanthium pungens	LOTUS Database	35616633

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
Acetophenone
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
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	3.09	ALOGPS
logP	2.43	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	16.24	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.85 m³·mol⁻¹	ChemAxon
Polarizability	22.56 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

HMDB0030816

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002772

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

177040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Acetyl-2,2-dimethyl-2H-1-benzopyran (NP0046038)

MOL for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

3D MOL for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

3D SDF for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

3D-SDF for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

PDB for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

3D PDB for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

SMILES for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

INCHI for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

Structure for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)

3D Structure for NP0046038 (6-Acetyl-2,2-dimethyl-2H-1-benzopyran)