NP-MRD: Showing NP-Card for Dillapiol (NP0045999)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:44 UTC

Updated at

2022-03-17 19:46:44 UTC

NP-MRD ID

NP0045999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dillapiol

Description

Dillapiol, also known as apiole (dill), belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Dillapiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Dillapiol is a spice and wood tasting compound. Outside of the human body, Dillapiol is found, on average, in the highest concentration within dills and cumins. Dillapiol has also been detected, but not quantified in, several different foods, such as corianders, fennels, herbs and spices, and parsley. This could make dillapiol a potential biomarker for the consumption of these foods. Dillapiol is found in Anethum sowa , Asarum yaeyamense, Brucea javanica, Bunium persicum, Codonopsis cordifolioidea, Coriandrum sativum, Crithmum maritimum , Endicheria aff., Erigeron spp., Laurelia serrata, Ligusticum scoticum , Ocotea aciphylla, Peperomia pellucida, Perilla frutescens, Peucedanum zenkeri, Pimpinella serbica, Piper aduncum , Piper auritum, Piper guineense, Piper marginatum, Piper novae-hollandiae, Piper pedicellosum, Piper regnellii, Piper solmsianum, Piper spp., Protium heptaphyllum, Stellaria pallida, Tipuana tipu and Xylopia sericea . Dillapiol is an organic chemical compound and essential oil commonly extracted from dill weed, though can be found in a variety of other plants.

Structure

MOL SDF PDB SMILES InChI

Dillapiole
  Mrv1652309251700152D          

 16 17  0  0  0  0            999 V2000
    1.7383   -0.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383    0.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -0.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -1.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190    0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 12  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
 11 13  1  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(CC=C)=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

> <INCHI_KEY>
LIKYNOPXHGPMIH-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.944835214004673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.3797074853333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.401145947371453

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
59.03860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dillapiol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dillapiole                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-17         0                                  
HETATM    1  O   UNK     0       3.245  -1.143   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.245   1.335   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.703  -1.444   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.036  -2.984   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.370   0.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.702  -0.674   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.702   0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.370  -0.674   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.036  -1.444   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.036   1.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.703   1.636   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.346   0.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.703   3.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.037  -0.674   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.370  -3.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.037   3.946   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    7   12                                                       
CONECT    3    8   14                                                       
CONECT    4    9   15                                                       
CONECT    5    8   10   11                                                  
CONECT    6    1    7    9                                                  
CONECT    7    2    6   10                                                  
CONECT    8    3    5    9                                                  
CONECT    9    4    6    8                                                  
CONECT   10    5    7                                                       
CONECT   11    5   13                                                       
CONECT   12    1    2                                                       
CONECT   13   11   16                                                       
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9ci)	HMDB
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)-benzene	HMDB
1-Allyl-2,3-dimethoxy-4,5-methylenedioxybenzene	HMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole	HMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
6-Allyl-4,5-dimethoxy-1,3-benzodioxole	HMDB
Apiole (dill)	HMDB
Dill apiol	HMDB
Dill apiole	HMDB
Dillapiole	HMDB
Dillapiol	KEGG
2-Methyl-5-(1-methylethenyl)-1,3-benzodioxole	MeSH
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene	MeSH
5-Allyl 6,7-dimethoxy 1,3-benzodioxole	MeSH

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2372 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

dillapiol

CAS Registry Number

484-31-1

SMILES

COC1=C(OC)C(CC=C)=CC2=C1OCO2

InChI Identifier

InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

InChI Key

LIKYNOPXHGPMIH-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
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anethum sowa	Plant	KNApSAcK
Asarum yaeyamense	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Bunium persicum	Plant	KNApSAcK
Codonopsis cordifolioidea	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crithmum maritimum	Plant	KNApSAcK
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Endicheria aff.	-	KNApSAcK
Erigeron spp.	Plant	KNApSAcK
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Laurelia serrata	Plant	KNApSAcK
Ligusticum scoticum	Plant	KNApSAcK
Ocotea aciphylla	LOTUS Database	35616633
Peperomia pellucida	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Peucedanum zenkeri	LOTUS Database	35616633
Pimpinella serbica	LOTUS Database	35616633
Piper aduncum	Plant	KNApSAcK
Piper auritum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper marginatum	LOTUS Database	35616633
Piper novae-hollandiae	Plant	KNApSAcK
Piper pedicellosum	LOTUS Database	35616633
Piper regnellii	LOTUS Database	35616633
Piper solmsianum	LOTUS Database	35616633
Piper spp.	Plant	KNApSAcK
Protium heptaphyllum	LOTUS Database	35616633
Stellaria pallida	Plant	KNApSAcK
Tipuana tipu	Plant	KNApSAcK
Xylopia sericea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:70453 )

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	2.33	ALOGPS
logP	2.38	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.04 m³·mol⁻¹	ChemAxon
Polarizability	22.94 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