NP-MRD: Showing NP-Card for 6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one (NP0183260)

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Record Information

Version

2.0

Created at

2022-09-03 22:08:27 UTC

Updated at

2022-09-03 22:08:27 UTC

NP-MRD ID

NP0183260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

Description

6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxy-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. 6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by enzyme via a catechol-O-methylation-pattern2 reaction. 6--4-Methoxy-2h-pyran-2-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 6--4-methoxy-2h-pyran-2-one. This catechol-O-methylation-pattern2 occurs in humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.6818   -0.6634    2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1892   -0.3095    1.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990   -0.0365    0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9309   -0.0928    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    0.1783   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.1025   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397    0.3599   -1.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    0.3079   -1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456    0.6130   -2.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158    0.5939   -2.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486    0.2651   -1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8401    0.2271   -0.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154   -0.0370    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3700   -0.3616    1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7084   -0.6859    2.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.0187    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574    0.5016   -1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    0.5730   -1.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2026    0.8957   -3.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665    0.3101   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082   -0.9618    3.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654    0.1907    3.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115   -1.4770    2.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677   -0.3697    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -0.1642    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2212    0.6265   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418    0.8686   -3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4072    0.8301   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3815    0.4514   -1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -1.4304    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4065   -1.0918    3.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    0.1703    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -0.2543    0.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8287    0.3737   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  8  1  0
  8 16  2  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 20  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
  9  8  1  0
 17  5  1  0
  6 25  1  0
  7 26  1  0
 16 33  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 12 29  1  0
 10 28  1  0
  9 27  1  0
  4 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 20 34  1  0
M  END


  Mrv1652308221902412D          

 22 23  0  0  0  0            999 V2000
    3.5724   -8.6625    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   -4.9500    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
    2.1434   -5.3625    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    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   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    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
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  1  1  0  0  0  0
 18 12  1  0  0  0  0
 19  2  1  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 21  3  1  0  0  0  0
 22  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C1=CC(OC)=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-13(16)14(7-10)19-2/h3-9,16H,1-2H3/b5-3+

> <INCHI_KEY>
YHVDGZPFCGLBOW-HWKANZROSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.322033539267245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.1782532876666663

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.929827691182952

> <JCHEM_PKA_STRONGEST_BASIC>
-4.558218149073936

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.1848

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       1.334 -10.010   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.335  -9.240   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    5   10   21                                                  
CONECT    4    6   10                                                       
CONECT    5    3   11   22                                                  
CONECT    6    4   13                                                       
CONECT    7   10   14                                                       
CONECT    8   11   12                                                       
CONECT    9   12   15                                                       
CONECT   10    3    4    7                                                  
CONECT   11    5    8   20                                                  
CONECT   12    8    9   18                                                  
CONECT   13    6   14   16                                                  
CONECT   14    7   13   19                                                  
CONECT   15    9   17   20                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18    1   12                                                       
CONECT   19    2   14                                                       
CONECT   20   11   15                                                       
CONECT   21    3                                                            
CONECT   22    5                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

Traditional Name

6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C1=CC(OC)=CC(=O)O1

InChI Identifier

InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-13(16)14(7-10)19-2/h3-9,16H,1-2H3/b5-3+

InChI Key

YHVDGZPFCGLBOW-HWKANZROSA-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

Not Available

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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen 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	2.3	ALOGPS
logP	2.18	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.18 m³·mol⁻¹	ChemAxon
Polarizability	28.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0131119

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4477768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one (NP0183260)

MOL for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

3D MOL for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

3D SDF for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

3D-SDF for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

PDB for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

3D PDB for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

SMILES for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

INCHI for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

Structure for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)

3D Structure for NP0183260 (6-[(1e)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4-methoxypyran-2-one)