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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:30:17 UTC

Update Date

2021-09-26 22:58:27 UTC

HMDB ID

HMDB0248258

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alpinetin

Description

Alpinetin belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Thus, alpinetin is considered to be a flavonoid. Based on a literature review very few articles have been published on Alpinetin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpinetin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Alpinetin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248258
     RDKit          3D
Alpinetin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.9001    1.5075    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5273    1.3520    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    0.1370    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.0815    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -2.2732    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202   -3.5054    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -2.2672   -0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153   -1.0481   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.1214   -0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232    1.4063   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.4858    0.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    1.4337   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445    0.1131    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    0.1468   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.4353    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    0.4866    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3940    0.2383   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -0.0541   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -0.0960   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527   -0.9867   -0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    1.5023    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4507    0.7047    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.4646    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5953   -1.1131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876   -3.8716   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -3.1752   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.5573   -1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    2.2291    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    0.0772    1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    0.6391    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6752    0.7121    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593    0.2810   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173   -0.2381   -2.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448   -0.3209   -2.2363 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
  9  3  1  0
 19 14  1  0
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv1652310051703202D          

 20 22  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 16 12  1  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19  1  1  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248258

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C(=O)CC(OC2=CC(O)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-19-14-7-11(17)8-15-16(14)12(18)9-13(20-15)10-5-3-2-4-6-10/h2-8,13,17H,9H2,1H3

> <INCHI_KEY>
QQQCWVDPMPFUGF-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.282934961869813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.6345674279999995

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.565319259742523

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.857218605502858

> <JCHEM_PKA_STRONGEST_BASIC>
-4.621002087490312

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
73.7912

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alpinetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248258
     RDKit          3D
Alpinetin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.9001    1.5075    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5273    1.3520    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    0.1370    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.0815    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -2.2732    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202   -3.5054    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -2.2672   -0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153   -1.0481   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.1214   -0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232    1.4063   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.4858    0.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    1.4337   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445    0.1131    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    0.1468   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.4353    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    0.4866    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3940    0.2383   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -0.0541   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -0.0960   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527   -0.9867   -0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    1.5023    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4507    0.7047    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.4646    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5953   -1.1131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876   -3.8716   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -3.1752   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.5573   -1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    2.2291    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    0.0772    1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    0.6391    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6752    0.7121    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593    0.2810   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173   -0.2381   -2.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448   -0.3209   -2.2363 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
  9  3  1  0
 19 14  1  0
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7   11   14                                                       
CONECT    8   11   15                                                       
CONECT    9   12   13                                                       
CONECT   10    5    6   13                                                  
CONECT   11    7    8   17                                                  
CONECT   12    9   16   18                                                  
CONECT   13    9   10   20                                                  
CONECT   14    7   16   19                                                  
CONECT   15    8   16   20                                                  
CONECT   16   12   14   15                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    1   14                                                       
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0248258
HETATM    1  C1  UNL     1      -4.900   1.507   0.617  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.527   1.352   0.385  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.896   0.137   0.222  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.529  -1.082   0.265  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.851  -2.273   0.096  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.520  -3.505   0.145  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.490  -2.267  -0.126  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.815  -1.048  -0.177  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.530   0.121  -0.003  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.823   1.406  -0.056  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.432   2.486   0.101  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.631   1.434  -0.297  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.244   0.113   0.141  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.662   0.147  -0.199  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.582   0.435   0.785  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.946   0.487   0.544  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.394   0.238  -0.733  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.504  -0.054  -1.745  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.162  -0.096  -1.469  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.553  -0.987  -0.398  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.134   1.502   1.716  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.451   0.705   0.083  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.302   2.465   0.225  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.595  -1.113   0.438  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.888  -3.872  -0.725  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.919  -3.175  -0.264  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.885   1.557  -1.370  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.129   2.229   0.327  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.136   0.077   1.243  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.276   0.639   1.812  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.675   0.712   1.310  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.459   0.281  -0.909  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.917  -0.238  -2.720  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.445  -0.321  -2.236  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   26
CONECT    8    9    9   20
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   27   28
CONECT   13   14   20   29
CONECT   14   15   15   19
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   34
END

HMDB0248258
     RDKit          3D
Alpinetin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.9001    1.5075    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5273    1.3520    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    0.1370    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.0815    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -2.2732    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202   -3.5054    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -2.2672   -0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153   -1.0481   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    0.1214   -0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232    1.4063   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.4858    0.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    1.4337   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445    0.1131    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    0.1468   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.4353    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    0.4866    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3940    0.2383   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -0.0541   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -0.0960   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527   -0.9867   -0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    1.5023    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4507    0.7047    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.4646    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5953   -1.1131    0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876   -3.8716   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -3.1752   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.5573   -1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    2.2291    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    0.0772    1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    0.6391    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6752    0.7121    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593    0.2810   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173   -0.2381   -2.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448   -0.3209   -2.2363 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
  9  3  1  0
 19 14  1  0
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.284

Monoisotopic Molecular Weight

270.089208931

IUPAC Name

7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

alpinetin

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)CC(OC2=CC(O)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O4/c1-19-14-7-11(17)8-15-16(14)12(18)9-13(20-15)10-5-3-2-4-6-10/h2-8,13,17H,9H2,1H3

InChI Key

QQQCWVDPMPFUGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140215 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.38	ALOGPS
logP	2.63	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.79 m³·mol⁻¹	ChemAxon
Polarizability	28.28 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	163.147	30932474
DeepCCS	[M-H]-	160.789	30932474
DeepCCS	[M-2H]-	193.675	30932474
DeepCCS	[M+Na]+	169.24	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	165.2	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpinetin	COC1=C2C(=O)CC(OC2=CC(O)=C1)C1=CC=CC=C1	3580.9	Standard polar	33892256
Alpinetin	COC1=C2C(=O)CC(OC2=CC(O)=C1)C1=CC=CC=C1	2525.9	Standard non polar	33892256
Alpinetin	COC1=C2C(=O)CC(OC2=CC(O)=C1)C1=CC=CC=C1	2622.2	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 - 7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kou-2590000000-968d5c2630c47f37f4eb	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-hydroxy-5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 20V, Negative-QTOF	splash10-014i-2690000000-f5e70063a2f05ca7b52c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 40V, Negative-QTOF	splash10-014l-9300000000-afbcdb568a343e46a90c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 20V, Positive-QTOF	splash10-014i-0910000000-49dba9b03acffcbc3f28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 10V, Positive-QTOF	splash10-00di-0390000000-dc00c836f62e23fcbdc3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 40V, Positive-QTOF	splash10-0gb9-2900000000-aff1fcaed61587b9fede	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpinetin 10V, Negative-QTOF	splash10-014i-0090000000-8c2a9ae08ba4d0d92ee8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 10V, Positive-QTOF	splash10-00di-0290000000-5a19a9e0b3154745703d	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 20V, Positive-QTOF	splash10-0v4m-2940000000-0525113aa27bbf8fe261	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 40V, Positive-QTOF	splash10-0udi-4900000000-e431c51c29507b168994	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 10V, Negative-QTOF	splash10-014i-0090000000-b94a7e62b653cf0f0d5c	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 20V, Negative-QTOF	splash10-014i-0290000000-c57570de2a1907887f7b	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 40V, Negative-QTOF	splash10-0ufr-7910000000-f28c30f6f55a2044afed	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 10V, Positive-QTOF	splash10-00di-0090000000-be8e31059a494fbfce6d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 20V, Positive-QTOF	splash10-01ba-0940000000-8a2f989d5b3341d1d2a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 40V, Positive-QTOF	splash10-014i-0900000000-c42e38a28b60ca27cc54	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 10V, Negative-QTOF	splash10-014i-0090000000-3027ecbd59fd767f7f5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 20V, Negative-QTOF	splash10-014i-0980000000-f870de8d9e012e24b126	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpinetin 40V, Negative-QTOF	splash10-0udi-0900000000-d4c2f6149c068db04748	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00008143

Chemspider ID

3269072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpinetin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Alpinetin (HMDB0248258)

MOL for HMDB0248258 (Alpinetin)

3D MOL for HMDB0248258 (Alpinetin)

3D SDF for HMDB0248258 (Alpinetin)

3D-SDF for HMDB0248258 (Alpinetin)

PDB for HMDB0248258 (Alpinetin)

3D PDB for HMDB0248258 (Alpinetin)

SMILES for HMDB0248258 (Alpinetin)

INCHI for HMDB0248258 (Alpinetin)

Structure for HMDB0248258 (Alpinetin)

3D Structure for HMDB0248258 (Alpinetin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra