NP-MRD: Showing NP-Card for (5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran (NP0249708)

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Record Information

Version

2.0

Created at

2022-09-07 12:20:57 UTC

Updated at

2022-09-07 12:20:57 UTC

NP-MRD ID

NP0249708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran

Description

Davana ether belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. (5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran is found in Chrysanthemum indicum. (5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran was first documented in 2018 (PMID: 29580507). Based on a literature review very few articles have been published on Davana ether (PMID: 34669255).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.7646    0.8019    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    1.1269    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    0.4493   -0.0297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9040    1.0003   -1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0372   -1.0115   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -1.6725   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266   -0.6366    0.8736 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4904   -1.0038    0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8862   -2.4047    1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4013   -0.1603    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    1.2072   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864    1.6794   -0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.6071   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2113    0.2337   -1.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529    0.9915    0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7456   -0.5122    0.2666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221    0.5232    0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1902    0.0050    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3968    1.2891    1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0889    1.9372    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404    0.7258   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979    0.5236   -1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    2.0860   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -1.3218    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5803   -1.2891   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -2.6388    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -1.6591   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -0.7580    1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -3.0973    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566   -2.3987    1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -2.6989    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    1.7816   -0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6733    2.6651   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405    0.8978   -2.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -0.8399   -1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2937    0.4341   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    1.0085    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9251    1.9718    0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046    0.1572    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3 17  1  0
  3  2  1  1
  2  1  2  3
  8 10  2  0
 10 16  1  0
 16 13  1  0
 13 14  1  0
 13 15  1  0
 13 12  1  0
 12 11  2  0
 17  7  1  0
 11 10  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
  7 28  1  1
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  2 20  1  0
  1 18  1  0
  1 19  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 12 33  1  0
 11 32  1  0
M  END


  Mrv1652309072214202D          

 17 18  0  0  0  0            999 V2000
    0.3150   -0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700   -0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -3.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439   -4.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -4.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493   -5.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044   -5.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -6.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -5.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -4.8775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6495   -1.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 10 16  1  0  0  0  0
  7 17  1  0  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(C1CCC(C)(O1)C=C)=C1/OC(C)(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-6-15(5)10-8-13(17-15)11(2)12-7-9-14(3,4)16-12/h6-7,9,13H,1,8,10H2,2-5H3/b12-11+

> <INCHI_KEY>
ZFMNPTVNDZBEHA-VAWYXSNFSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.740186338025893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethyl-2,5-dihydrofuran

> <JCHEM_LOGP>
2.927107391666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.148602341514547

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
72.34550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.588  -0.139   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.064  -1.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.033  -2.748   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.997  -1.604   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.279  -3.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.803  -5.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.737  -5.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.642  -6.364   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.173  -6.203   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.015  -7.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.491  -8.091   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.652  -9.623   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.755 -10.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.015 -11.583   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001 -11.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.785  -9.105   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.212  -3.654   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   17                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   10                                                       
CONECT   17    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C(C1CCC(C)(O1)C=C)=C1/OC(C)(C)C=C1

InChI Identifier

InChI=1S/C15H22O2/c1-6-15(5)10-8-13(17-15)11(2)12-7-9-14(3,4)16-12/h6-7,9,13H,1,8,10H2,2-5H3/b12-11+

InChI Key

ZFMNPTVNDZBEHA-VAWYXSNFSA-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
Chrysanthemum indicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Dihydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011442

Chemspider ID

4520996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5370105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh S, Bhatt D, Singh MK, Sundaresan V, Tandon S, Padalia RC, Bawankule DU, Verma RS: New Insights into the Chemical Composition, Pro-Inflammatory Cytokine Inhibition Profile of Davana (Artemisia pallens Wall. ex DC.) Essential Oil and cis-Davanone in Primary Macrophage Cells. Chem Biodivers. 2021 Nov;18(11):e2100531. doi: 10.1002/cbdv.202100531. Epub 2021 Oct 20. [PubMed:34669255 ]
Mojtahed Zadeh Asl R, Niakousari M, Hashemi Gahruie H, Saharkhiz MJ, Mousavi Khaneghah A: Study of two-stage ohmic hydro-extraction of essential oil from Artemisia aucheri Boiss.: Antioxidant and antimicrobial characteristics. Food Res Int. 2018 May;107:462-469. doi: 10.1016/j.foodres.2018.02.059. Epub 2018 Feb 27. [PubMed:29580507 ]
LOTUS database [Link]

Showing NP-Card for (5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran (NP0249708)

MOL for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

3D MOL for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

3D SDF for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

3D-SDF for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

PDB for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

3D PDB for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

SMILES for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

INCHI for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

Structure for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)

3D Structure for NP0249708 ((5e)-5-[1-(5-ethenyl-5-methyloxolan-2-yl)ethylidene]-2,2-dimethylfuran)