NP-MRD: Showing NP-Card for 4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one (NP0167537)

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Record Information

Version

2.0

Created at

2022-09-03 03:08:06 UTC

Updated at

2022-09-03 03:08:06 UTC

NP-MRD ID

NP0167537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one

Description

Kavain, also known as neuronica, belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Kavain is an extremely weak basic (essentially neutral) compound (based on its pKa). How this effect is mediated and to what extent this mechanism is involved in the anxiolytic and analgesic effects of kavalactones on the central nervous system is unknown. Kavain is the main kavalactone found mostly in the roots of the kava plant. In 2016 kavain was shown to bind at the α4β2δ GABAA receptor and potentiate GABA efficacy. A comparative review of in-vivo studies with kavain (and related kavapyrones) to commonly used antiepileptic drugs and mood stabilizers affecting ion fluxes indicates that the kavapyrones are weakly Na+ antagonistic and therefore antiepileptic. Kavain has anticonvulsive properties, attenuating vascular smooth muscle contraction through interactions with voltage-dependent Na+ and Ca2+ channels. Kavain and analogs remain interesting for drug discovery against a variety of cellular targets, including P-glycoprotein (Pgp), cytochrome P450 and cyclo-oxygenase (COX) enzymes, among others. The mechanism behind the psychotropic, sedative and anxiolytic actions of kavain and related kavalactones is still debated. 4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one is found in Piper methysticum. Direct binding to the benzodiazepine/flumazenil binding site of the GABA-A receptor does not occur with kavain enantiomers.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.0148    1.2415    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1297    0.6612   -0.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288   -0.1821   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698   -1.3009    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256   -2.2647    0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397   -3.3409    1.2306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -1.9215    0.6160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -1.0952   -0.4653 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5556   -0.8639   -0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598    0.0820    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    0.3226    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861   -0.4004   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390   -0.1366   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3545    0.8862    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    1.6330    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    1.3543    0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    0.1878   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640    1.8825   -0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4963    0.3751    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871    1.7695    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6384   -1.5408    0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879   -1.6469   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665   -1.4969   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    0.7085    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1568   -1.2018   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117   -0.7347   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4281    1.1004    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094    2.4332    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    1.9731    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124    0.9187    0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    0.5976   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 17  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 17  3  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  8 22  1  6
 17 30  1  0
 17 31  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1533004171505552D          

 17 18  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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
 10  8  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(C1)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3

> <INCHI_KEY>
XEAQIWGXBXCYFX-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.263

> <EXACT_MASS>
230.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.966599517853695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-(2-phenylethenyl)-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.4327116786666663

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.541493371180767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788416686866828

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
67.35770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Neuronica	MeSH
Kavain, (e)-(+-)-isomer	MeSH
Kavaine	MeSH
Kavain, (+-)-isomer	MeSH
Kawain	MeSH
Cavain	MeSH
Kavain, (R)-isomer	MeSH
Neuronika	MeSH
Kavain, (R)-(e)-isomer	MeSH

Chemical Formula

C₁₄H₁₄O₃

Average Mass

230.2630 Da

Monoisotopic Mass

230.09429 Da

IUPAC Name

4-methoxy-6-(2-phenylethenyl)-5,6-dihydro-2H-pyran-2-one

Traditional Name

4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(C1)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3

InChI Key

XEAQIWGXBXCYFX-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, 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
Piper methysticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Styrene
Dihydropyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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
logP	2.96	ALOGPS
logP	2.43	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.36 m³·mol⁻¹	ChemAxon
Polarizability	24.97 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Kavain

METLIN ID

Not Available

PubChem Compound

10376

PDB ID

Not Available

ChEBI ID

91863

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one (NP0167537)

MOL for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

3D MOL for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

3D SDF for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

3D-SDF for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

PDB for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

3D PDB for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

SMILES for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

INCHI for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

Structure for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)

3D Structure for NP0167537 (4-methoxy-6-(2-phenylethenyl)-5,6-dihydropyran-2-one)