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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-29 15:36:32 UTC

Update Date

2022-11-23 21:39:02 UTC

HMDB ID

HMDB0242309

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

Description

(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one, also known as hylin, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Based on a literature review very few articles have been published on (1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1e,4e)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 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

HMDB0242309
     RDKit          3D
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
 42 43  0  0  0  0  0  0  0  0999 V2000
    8.2324   -1.6308    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0908   -1.0576   -0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -0.5267   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225   -1.1431    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4457   -0.5799    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3040   -1.3073    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.2013    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024   -0.3116    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.7659   -0.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256   -0.6455    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    0.1832    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.0666    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.1943    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5439   -1.4123    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4604   -0.4755    0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -0.6814    0.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0659    0.6860    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0302    1.5960   -0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867    2.7723   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3664    0.6509   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318    1.3008   -0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.7370   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6193   -1.5568    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.1297   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -1.9605    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8201   -2.3260    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4737    0.0129    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4489    3.4974   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970    3.2688   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    2.5656   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    1.7670   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    1.1412   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    2.2677   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191518182D          

 24 25  0  0  0  0            999 V2000
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    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242309

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C=CC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O5/c1-23-18-11-13(5-9-16(18)21)3-7-15(20)8-4-14-6-10-17(22)19(12-14)24-2/h3-12,21-22H,1-2H3

> <INCHI_KEY>
ISIMGBQRFXXNON-UHFFFAOYSA-N

> <FORMULA>
C19H18O5

> <MOLECULAR_WEIGHT>
326.348

> <EXACT_MASS>
326.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.137311556465406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.902670582333333

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.805976591295552

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20391659940859

> <JCHEM_PKA_STRONGEST_BASIC>
-4.331575407940574

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
93.9154

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242309
     RDKit          3D
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
 42 43  0  0  0  0  0  0  0  0999 V2000
    8.2324   -1.6308    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0908   -1.0576   -0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -0.5267   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225   -1.1431    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4457   -0.5799    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3040   -1.3073    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.2013    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024   -0.3116    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.7659   -0.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256   -0.6455    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    0.1832    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.0666    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.1943    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5439   -1.4123    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4604   -0.4755    0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -0.6814    0.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0659    0.6860    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0302    1.5960   -0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867    2.7723   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268    0.8613   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.6509   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318    1.3008   -0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.7370   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9335    1.3660   -1.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7970    3.2688   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    2.5656   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    1.7670   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    1.1412   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    2.2677   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381    2.2656   -1.6844 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
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  6  7  2  3
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  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
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 17 18  1  0
 18 19  1  0
 17 20  2  0
  5 21  2  0
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 22 23  2  0
 23 24  1  0
 23  3  1  0
 20 12  1  0
  1 25  1  0
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 16 35  1  0
 19 36  1  0
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 20 39  1  0
 21 40  1  0
 22 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   12                                                       
CONECT   21    5   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0242309
HETATM    1  C1  UNL     1       8.232  -1.631   0.093  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.091  -1.058  -0.081  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.908  -0.527  -0.230  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.722  -1.143   0.180  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.446  -0.580   0.023  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.304  -1.307   0.491  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.041  -1.201   0.533  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.002  -0.312   0.149  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.150   0.766  -0.430  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.426  -0.646   0.439  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.350   0.183   0.077  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.757  -0.067   0.321  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.189  -1.194   0.948  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.544  -1.412   1.173  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.460  -0.475   0.757  1.00  0.00           C  
HETATM   16  O3  UNL     1      -7.812  -0.681   0.976  1.00  0.00           O  
HETATM   17  C14 UNL     1      -6.066   0.686   0.115  1.00  0.00           C  
HETATM   18  O4  UNL     1      -7.030   1.596  -0.283  1.00  0.00           O  
HETATM   19  C15 UNL     1      -6.587   2.772  -0.936  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.727   0.861  -0.086  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.366   0.651  -0.568  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.532   1.301  -0.993  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.749   0.737  -0.830  1.00  0.00           C  
HETATM   24  O5  UNL     1       6.933   1.366  -1.246  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.884  -1.614  -0.855  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.951  -1.170   0.848  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.238  -2.753   0.319  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.846  -2.114   0.640  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.653  -2.308   0.989  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.551  -2.138   1.059  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.619  -1.557   0.934  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.118   1.130  -0.441  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.499  -1.960   1.293  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.820  -2.326   1.675  1.00  0.00           H  
HETATM   35  H11 UNL     1      -8.474   0.013   0.665  1.00  0.00           H  
HETATM   36  H12 UNL     1      -7.449   3.497  -0.971  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.797   3.269  -0.336  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.242   2.566  -1.971  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.407   1.767  -0.587  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.429   1.141  -0.717  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.409   2.268  -1.452  1.00  0.00           H  
HETATM   42  H18 UNL     1       6.938   2.266  -1.684  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6   21   21
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9    9   10
CONECT   10   11   11   31
CONECT   11   12   32
CONECT   12   13   13   20
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16   17
CONECT   16   35
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   39
CONECT   21   22   40
CONECT   22   23   23   41
CONECT   23   24
CONECT   24   42
END

HMDB0242309
     RDKit          3D
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
 42 43  0  0  0  0  0  0  0  0999 V2000
    8.2324   -1.6308    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0908   -1.0576   -0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -0.5267   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225   -1.1431    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4457   -0.5799    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3040   -1.3073    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.2013    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024   -0.3116    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.7659   -0.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256   -0.6455    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    0.1832    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572   -0.0666    0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.1943    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5439   -1.4123    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4604   -0.4755    0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -0.6814    0.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0659    0.6860    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0302    1.5960   -0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867    2.7723   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268    0.8613   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.6509   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318    1.3008   -0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.7370   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9335    1.3660   -1.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8843   -1.6140   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9515   -1.1698    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2377   -2.7532    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8462   -2.1136    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6528   -2.3085    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5508   -2.1384    1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6193   -1.5568    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.1297   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -1.9605    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8201   -2.3260    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4737    0.0129    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4489    3.4974   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970    3.2688   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    2.5656   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    1.7670   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    1.1412   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092    2.2677   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381    2.2656   -1.6844 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
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one	HMDB
Hylin	HMDB

Chemical Formula

C₁₉H₁₈O₅

Average Molecular Weight

326.348

Monoisotopic Molecular Weight

326.11542368

IUPAC Name

1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

Traditional Name

1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C19H18O5/c1-23-18-11-13(5-9-16(18)21)3-7-15(20)8-4-14-6-10-17(22)19(12-14)24-2/h3-12,21-22H,1-2H3

InChI Key

ISIMGBQRFXXNON-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Anisole
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

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	3.31	ALOGPS
logP	3.9	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.92 m³·mol⁻¹	ChemAxon
Polarizability	35.14 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
DeepCCS	[M+H]+	172.208	30932474
DeepCCS	[M-H]-	169.85	30932474
DeepCCS	[M-2H]-	204.07	30932474
DeepCCS	[M+Na]+	179.925	30932474

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.	7.51 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9748 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2280.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.5 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	623.3 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	428.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1317.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	450.0 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	1165.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	308.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	264.2 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one	COC1=CC(C=CC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O	5583.7	Standard polar	33892256
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one	COC1=CC(C=CC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O	3064.9	Standard non polar	33892256
(1E,4E)-1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one	COC1=CC(C=CC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O	3337.5	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 - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-0915000000-d4ad13b17236b3f6605d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-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 - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 10V, Positive-QTOF	splash10-004i-0049000000-02b0f1eba0ebc903b508	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 20V, Positive-QTOF	splash10-002b-0962000000-3a6ac4ed5db5b539a3d5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 40V, Positive-QTOF	splash10-004i-4590000000-8e56abbaa4f0f78c39f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 10V, Negative-QTOF	splash10-004i-0009000000-b529a9e38a14ff67038c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 20V, Negative-QTOF	splash10-00b9-0709000000-7890ea36ae629df0d781	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 40V, Negative-QTOF	splash10-00ei-0965000000-76bf21f0a3e10faf0f39	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

468133

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 (1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one (HMDB0242309)

MOL for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

3D MOL for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

3D SDF for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

3D-SDF for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

PDB for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

3D PDB for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

SMILES for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

INCHI for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

Structure for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

3D Structure for HMDB0242309 ((1E,4E)-1,5-bis(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra