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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:33 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030549

Secondary Accession Numbers

HMDB30549

Metabolite Identification

Common Name

5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one

Description

5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one, also known as 5,6,7,8-tetrahydroyangonin, 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. Based on a literature review very few articles have been published on 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030549
     RDKit          3D
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.1944    1.6746    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2432    0.2762    0.4887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.4411   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.5883   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -2.3760   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4570   -3.4648   -1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -1.8199   -1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.3709   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    0.0241   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1089   -0.5362    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -0.1521    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    1.0190    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    1.3910    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.6183    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.0726    0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588    0.3885    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -0.5585   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.9218   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.0888    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362    2.0451    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.1221   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1172    2.0541    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.9444   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148    0.0180   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -0.4268   -1.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.1431   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128   -1.6280    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -0.0960    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    1.6283    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    2.3231    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9011    0.7640   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5427   -0.7018    0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    0.5962    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -1.1817   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939   -1.8495   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.3874    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    1.1978    0.1237 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  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv0541 05061305202D          

 19 20  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    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
    1.4289   -4.9500    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
    2.1434   -5.3625    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
    1.4289   -2.4750    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   -7.4250    0.0000 C   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
    1.4289   -1.6500    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
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17  1  1  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030549

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-4,6-7,10,13H,5,8-9H2,1-2H3

> <INCHI_KEY>
IZGFAKZIDOQLHS-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.510579313631048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.398354609666666

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.42643962425681

> <JCHEM_PKA_STRONGEST_BASIC>
-4.504824321271525

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
72.8583

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030549
     RDKit          3D
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.1944    1.6746    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2432    0.2762    0.4887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.4411   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.5883   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -2.3760   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4570   -3.4648   -1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -1.8199   -1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.3709   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    0.0241   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1089   -0.5362    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -0.1521    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    1.0190    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    1.3910    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.6183    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.0726    0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588    0.3885    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -0.5585   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.9218   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.0888    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362    2.0451    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.1221   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1172    2.0541    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.9444   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148    0.0180   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -0.4268   -1.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.1431   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128   -1.6280    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -0.0960    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    1.6283    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    2.3231    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9011    0.7640   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5427   -0.7018    0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    0.5962    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -1.1817   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939   -1.8495   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.3874    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    1.1978    0.1237 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  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002 -13.860   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       2.667  -9.240   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  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   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       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -3.080   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       2.667 -12.320   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   13                                                       
CONECT    9   13   14                                                       
CONECT   10   14   15                                                       
CONECT   11    3    4    5                                                  
CONECT   12    6    7   17                                                  
CONECT   13    8    9   19                                                  
CONECT   14    9   10   18                                                  
CONECT   15   10   16   19                                                  
CONECT   16   15                                                            
CONECT   17    1   12                                                       
CONECT   18    2   14                                                       
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0030549
HETATM    1  C1  UNL     1      -5.194   1.675   0.513  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.243   0.276   0.489  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.152  -0.441  -0.061  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.368  -1.588  -0.661  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.301  -2.376  -1.250  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.457  -3.465  -1.822  1.00  0.00           O  
HETATM    7  O3  UNL     1      -2.009  -1.820  -1.137  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.954  -0.371  -1.118  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.516   0.024  -1.044  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.109  -0.536   0.200  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.556  -0.152   0.262  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.907   1.019   0.887  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.232   1.391   0.956  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.235   0.618   0.412  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.532   1.073   0.530  1.00  0.00           O  
HETATM   16  C12 UNL     1       6.659   0.389   0.023  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.893  -0.559  -0.217  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.555  -0.922  -0.279  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.781   0.089   0.039  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.336   2.045   1.096  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.128   2.122  -0.501  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.117   2.054   0.994  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.417  -1.944  -0.703  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.415   0.018  -2.069  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.030  -0.427  -1.917  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.416   1.143  -1.073  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.013  -1.628   0.186  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.377  -0.096   1.116  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.133   1.628   1.314  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.490   2.323   1.455  1.00  0.00           H  
HETATM   31  H12 UNL     1       6.901   0.764  -0.992  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.543  -0.702   0.001  1.00  0.00           H  
HETATM   33  H14 UNL     1       7.522   0.596   0.705  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.670  -1.182  -0.653  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.294  -1.849  -0.776  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.337  -0.387   0.960  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.756   1.198   0.124  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   19   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   12   18
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   17
CONECT   15   16
CONECT   16   31   32   33
CONECT   17   18   18   34
CONECT   18   35
CONECT   19   36   37
END

HMDB0030549
     RDKit          3D
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.1944    1.6746    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2432    0.2762    0.4887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.4411   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.5883   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -2.3760   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4570   -3.4648   -1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -1.8199   -1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.3709   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    0.0241   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1089   -0.5362    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -0.1521    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    1.0190    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    1.3910    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.6183    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.0726    0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588    0.3885    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -0.5585   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.9218   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.0888    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362    2.0451    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.1221   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1172    2.0541    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.9444   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148    0.0180   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -0.4268   -1.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.1431   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128   -1.6280    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -0.0960    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    1.6283    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    2.3231    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9011    0.7640   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5427   -0.7018    0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    0.5962    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -1.1817   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939   -1.8495   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.3874    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    1.1978    0.1237 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  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,7,8-Tetrahydroyangonin	HMDB

Chemical Formula

C₁₅H₁₈O₄

Average Molecular Weight

262.301

Monoisotopic Molecular Weight

262.120509064

IUPAC Name

4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydropyran-2-one

CAS Registry Number

49776-58-1

SMILES

COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1

InChI Identifier

InChI=1S/C15H18O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-4,6-7,10,13H,5,8-9H2,1-2H3

InChI Key

IZGFAKZIDOQLHS-UHFFFAOYSA-N

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
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Dihydropyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030549)
Cell membrane (HMDB: HMDB0030549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030549)

Source

Endogenous

Endogenous (HMDB: HMDB0030549)

Plant

Plant (HMDB: HMDB0030549)

Exogenous

Food

Food (HMDB: HMDB0030549)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0030549)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	89 - 90 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	429.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.87	ALOGPS
logP	2.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	16.43	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.86 m³·mol⁻¹	ChemAxon
Polarizability	28.51 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.448	31661259
DarkChem	[M-H]-	165.815	31661259
DeepCCS	[M+H]+	159.871	30932474
DeepCCS	[M-H]-	157.513	30932474
DeepCCS	[M-2H]-	190.601	30932474
DeepCCS	[M+Na]+	165.964	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.27 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5224 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2369.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	434.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	247.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	631.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	692.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1393.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	533.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1483.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	424.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	378.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1	3280.3	Standard polar	33892256
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1	2196.4	Standard non polar	33892256
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1	2416.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-5950000000-8a3df98cf6c112a79d66	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Positive-QTOF	splash10-03di-0290000000-d73f7cd4a10407119183	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Positive-QTOF	splash10-01ot-1930000000-8271e8b3696d4038830a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Positive-QTOF	splash10-0pb9-4900000000-f1677005f630a2241c00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Negative-QTOF	splash10-03di-0090000000-a5b52057c6bf7fb41814	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Negative-QTOF	splash10-01ox-8190000000-4463596c1e2463c117a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Negative-QTOF	splash10-052f-9520000000-ff66beebcf4c1c30a378	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Positive-QTOF	splash10-01ot-0790000000-b1183b2d45a69d3cee0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Positive-QTOF	splash10-0002-1910000000-8a51733990160e1326ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Positive-QTOF	splash10-004l-9710000000-19546c1334387a67f123	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Negative-QTOF	splash10-000i-0900000000-d5fce93334c873464e4a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Negative-QTOF	splash10-000i-0900000000-7423acc6bb5078b1aef7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Negative-QTOF	splash10-014i-3900000000-678ef6594e8c4cad141d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002424

KNApSAcK ID

C00058121

Chemspider ID

8259588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10084050

PDB ID

Not Available

ChEBI ID

157716

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1820931

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one (HMDB0030549)

MOL for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

3D MOL for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

3D SDF for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

3D-SDF for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

PDB for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

3D PDB for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

SMILES for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

INCHI for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

Structure for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

3D Structure for HMDB0030549 (5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra