NP-MRD: Showing NP-Card for 5,6-Dehydrokawain (NP0051718)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:44 UTC

Updated at

2022-04-27 22:58:44 UTC

NP-MRD ID

NP0051718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dehydrokawain

Description

5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one, also known as 56-dehydrokawain or (e)-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one, 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. 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one has been detected, but not quantified in, beverages. This could make 5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-one a potential biomarker for the consumption of these foods. 5,6-Dehydrokawain is found in Alpinia blepharocalyx, Alpinia mutica, Alpinia roxburghii, Alpinia zerumbet, Aniba firmula, Boesenbergia rotunda, Alpinia speciosa , Lindera umbellata , Persicaria lapathifolia, Piper cubeba, Piper lolot, Piper methysticum and Piper sanctum. Found in kava (Piper methysticum).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -5.3740    0.8211    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911    1.0015    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507   -0.0968    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7611    0.0742    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8912   -0.9809   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679   -0.8466   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1360    0.3096    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5747    0.4720   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.7496    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014    1.9699    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407    0.8839   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -0.3700   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483   -0.5689   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4415   -2.1979   -0.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -2.3984   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321   -3.5968   -0.0665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496   -1.3754    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7763    0.5499    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7322    0.0647   -0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8337    1.7928   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    1.0859    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556   -1.7517   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5496    1.2244    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    2.5831    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681    2.9866    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235    1.0067   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4913   -1.2174   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -1.5909   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7162   -1.5844    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5  4  2  0
  4  3  1  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 17 29  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
  4 21  1  0
M  END


  Mrv0541 05061307412D          

 17 18  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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
    0.7145   -3.7125    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.0000    0.0000    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

> <INCHI_KEY>
DKKJNZYHGRUXBS-BQYQJAHWSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.2433

> <EXACT_MASS>
228.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.417347840506867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.639489875

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.827159191016256

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
68.7407

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desmethoxyyangonin

> <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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   12   13                                                       
CONECT   10   13   14                                                       
CONECT   11    5    6    7                                                  
CONECT   12    8    9   17                                                  
CONECT   13    9   10   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15   14                                                            
CONECT   16    1   13                                                       
CONECT   17   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
56-Dehydrokawain	HMDB
56-Dehydrokawin	HMDB
(e)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one	HMDB
2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (e)- (9ci)	HMDB
4-Methoxy-6-(2-phenylethenyl)-(e)-2H-pyran-2-one	HMDB
4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one	HMDB
4-Methoxy-6-styryl-(e)-2H-pyran-2-one	HMDB
4-Methoxy-6-styryl-2H-pyran-2-one	HMDB
4-Methoxy-6-[(e)-2-phenylethenyl]-2H-pyran-2-one	HMDB
4-Methoxy-6-[(e)-2-phenylvinyl]-2H-pyran-2-one	HMDB
5,6-Dehydrokawain	HMDB
Demethoxyyangonin	HMDB
Desmethoxyyangonin	HMDB
DMY	HMDB
5,6-Dehydrokawain, (e)-isomer	HMDB

Chemical Formula

C₁₄H₁₂O₃

Average Mass

228.2433 Da

Monoisotopic Mass

228.07864 Da

IUPAC Name

4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one

Traditional Name

desmethoxyyangonin

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

InChI Key

DKKJNZYHGRUXBS-BQYQJAHWSA-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
Alpinia blepharocalyx	LOTUS Database	35616633
Alpinia mutica	LOTUS Database	35616633
Alpinia roxburghii	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Aniba firmula	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Etlingera elatior	Plant	KNApSAcK
Lindera umbellata	Plant	KNApSAcK
Persicaria lapathifolia	LOTUS Database	35616633
Piper cubeba	LOTUS Database	35616633
Piper lolot	LOTUS Database	35616633
Piper methysticum	Plant	KNApSAcK
Piper sanctum	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
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:1995 )
2-pyranones (CHEBI:1995 )
alpha-Pyrones (C09925 )

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	3.2	ALOGPS
logP	2.64	ChemAxon
logS	-3.8	ALOGPS
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	68.74 m³·mol⁻¹	ChemAxon
Polarizability	24.42 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

HMDB0034270

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5273621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,6-Dehydrokawain (NP0051718)

MOL for NP0051718 (5,6-Dehydrokawain)

3D MOL for NP0051718 (5,6-Dehydrokawain)

3D SDF for NP0051718 (5,6-Dehydrokawain)

3D-SDF for NP0051718 (5,6-Dehydrokawain)

PDB for NP0051718 (5,6-Dehydrokawain)

3D PDB for NP0051718 (5,6-Dehydrokawain)

SMILES for NP0051718 (5,6-Dehydrokawain)

INCHI for NP0051718 (5,6-Dehydrokawain)

Structure for NP0051718 (5,6-Dehydrokawain)

3D Structure for NP0051718 (5,6-Dehydrokawain)