NP-MRD: Showing NP-Card for Isodillapiole (NP0045378)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:55 UTC

Updated at

2022-03-17 19:18:55 UTC

NP-MRD ID

NP0045378

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isodillapiole

Description

Isodillapiole 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. Isodillapiole is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isodillapiole has been detected, but not quantified in, dills and green vegetables. Isodillapiole is found in Polemannia montana. This could make isodillapiole a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.5727   -0.1189   -0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710    0.4005   -0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -0.3359   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    0.1739   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4851    1.4065   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.8973   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    1.0484   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -0.2045    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742   -1.0599    0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.9890   -0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719   -0.6564    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -1.9217    0.7176 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2084   -2.0484    2.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113    1.7135   -0.6222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7036    3.0958   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3475    3.0977   -1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -0.9236    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9176   -0.6195   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2487    0.7005    0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1047    1.3973   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -1.3144    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658    2.0977   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -1.6111   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0780   -2.4005    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -2.8272   -0.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -1.0504    2.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454   -2.3959    2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -2.7039    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    3.6663    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    3.4856   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 11  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
  7  8  1  0
 16  6  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
  3 21  1  0
  2 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 22  1  0
 15 29  1  0
 15 30  1  0
M  END


  Mrv0541 05061304472D          

 16 17  0  0  0  0            999 V2000
    3.4990   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(\C=C\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,7H2,1-3H3/b5-4+

> <INCHI_KEY>
OEDZKYGAFWDLGE-SNAWJCMRSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.46132708465631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.404473815

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.402073387557456

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
60.11110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dimethoxy-6-[(1E)-prop-1-en-1-yl]-2H-1,3-benzodioxole

> <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       6.531  -1.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    1    5                                                       
CONECT    5    4    8                                                       
CONECT    6    8    9                                                       
CONECT    7   15   16                                                       
CONECT    8    5    6   10                                                  
CONECT    9    6   11   15                                                  
CONECT   10    8   12   13                                                  
CONECT   11    9   12   16                                                  
CONECT   12   10   11   14                                                  
CONECT   13    2   10                                                       
CONECT   14    3   12                                                       
CONECT   15    7    9                                                       
CONECT   16    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dimethoxy-6-(1-propenyl)-1,3-benzodioxole, 9ci	HMDB

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2372 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

23731-63-7

SMILES

COC1=C(OC)C(\C=C\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,7H2,1-3H3/b5-4+

InChI Key

OEDZKYGAFWDLGE-SNAWJCMRSA-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
Polemannia montana	LOTUS Database	35616633

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
Styrene
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

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	2.33	ALOGPS
logP	2.4	ChemAxon
logS	-2.6	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	3	ChemAxon
Refractivity	60.11 m³·mol⁻¹	ChemAxon
Polarizability	23.46 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

HMDB0029470

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000592

KNApSAcK ID

Not Available

Chemspider ID

9610855

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11435991

PDB ID

Not Available

ChEBI ID

1156602

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isodillapiole (NP0045378)

MOL for NP0045378 (Isodillapiole)

3D MOL for NP0045378 (Isodillapiole)

3D SDF for NP0045378 (Isodillapiole)

3D-SDF for NP0045378 (Isodillapiole)

PDB for NP0045378 (Isodillapiole)

3D PDB for NP0045378 (Isodillapiole)

SMILES for NP0045378 (Isodillapiole)

INCHI for NP0045378 (Isodillapiole)

Structure for NP0045378 (Isodillapiole)

3D Structure for NP0045378 (Isodillapiole)