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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:56:55 UTC

Update Date

2021-09-26 23:17:48 UTC

HMDB ID

HMDB0259946

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Yakuchinone-A

Description

1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone, also known as yakuchinone-a, belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Yakuchinone-a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Yakuchinone-A 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

HMDB0259946
     RDKit          3D
Yakuchinone-A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.9583   -0.1508   -3.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6677   -0.8575   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209   -0.6981   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4297    0.1788   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.3416    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    1.2573    0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    0.4854    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351    1.4493    1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    2.4944    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928    1.1384    2.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.0627    2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982   -0.1754    1.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.2152    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -0.3281   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527    0.7636   -1.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    0.5920   -2.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447   -0.6755   -2.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812   -1.7863   -1.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -1.5876   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324   -0.3720    1.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.2273    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1492   -1.3953   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1396   -2.2695   -0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9405    2.0355    0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    0.0431    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -0.2781    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.1412    3.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    2.0634    2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3148   -1.0108    2.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -0.2013    3.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8048    0.5934    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.1425    1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643    0.6241    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419   -1.1406    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    1.7610   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6649    1.4116   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526   -0.8673   -3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -2.7988   -2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101   -2.4875   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.2080    2.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594   -1.7672    1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6689   -2.7813   -0.0375 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
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  5 20  2  0
 20 21  1  0
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 22  3  1  0
 19 14  1  0
  1 24  1  0
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 10 32  1  0
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 11 34  1  0
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 13 38  1  0
 13 39  1  0
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 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
M  END


  Mrv0541 04121517372D          

 23 24  0  0  0  0            999 V2000
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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  5 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259946

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CCC(=O)CCCCC2=CC=CC=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3

> <INCHI_KEY>
TXELARZTKDBEKS-UHFFFAOYSA-N

> <FORMULA>
C20H24O3

> <MOLECULAR_WEIGHT>
312.409

> <EXACT_MASS>
312.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.258648810492005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
5.091997520333333

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945876306662468

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890618736203671

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
92.48670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259946
     RDKit          3D
Yakuchinone-A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.9583   -0.1508   -3.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6677   -0.8575   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209   -0.6981   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4297    0.1788   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.3416    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    1.2573    0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    0.4854    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351    1.4493    1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    2.4944    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928    1.1384    2.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.0627    2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982   -0.1754    1.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.2152    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -0.3281   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527    0.7636   -1.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    0.5920   -2.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447   -0.6755   -2.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812   -1.7863   -1.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -1.5876   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324   -0.3720    1.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.2273    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1492   -1.3953   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1396   -2.2695   -0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5529   -0.1937   -4.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -0.5826   -3.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602    0.9012   -3.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172    0.7546   -1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    1.6401    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    2.0355    0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    0.0431    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -0.2781    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.1412    3.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3148   -1.0108    2.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -0.2013    3.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8048    0.5934    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.1425    1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643    0.6241    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419   -1.1406    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    1.7610   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6649    1.4116   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526   -0.8673   -3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -2.7988   -2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101   -2.4875   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.2080    2.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594   -1.7672    1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6689   -2.7813   -0.0375 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
M  END

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
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                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    5   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0259946
HETATM    1  C1  UNL     1      -3.958  -0.151  -3.573  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.668  -0.857  -2.575  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.421  -0.698  -1.209  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.430   0.179  -0.828  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.185   0.342   0.535  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.125   1.257   0.985  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.829   0.485   1.195  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.235   1.449   1.644  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.307   2.494   0.978  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.093   1.138   2.786  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.946  -0.063   2.751  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.998  -0.175   1.707  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.469  -0.215   0.320  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.573  -0.328  -0.686  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.153   0.764  -1.296  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.175   0.592  -2.180  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.645  -0.675  -2.477  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.081  -1.786  -1.879  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.038  -1.588  -0.980  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.932  -0.372   1.478  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.900  -1.227   1.056  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.149  -1.395  -0.272  1.00  0.00           C  
HETATM   23  O3  UNL     1      -6.140  -2.270  -0.734  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.553  -0.194  -4.537  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.957  -0.583  -3.778  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.860   0.901  -3.238  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.817   0.755  -1.539  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.427   1.640   1.990  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.941   2.036   0.241  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.569   0.043   0.197  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.969  -0.278   1.965  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.481   1.141   3.755  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.750   2.063   2.962  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.315  -1.011   2.676  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.401  -0.201   3.793  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.805   0.593   1.845  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.555  -1.143   1.939  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.864   0.624   0.012  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.842  -1.141   0.201  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.796   1.761  -1.077  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.665   1.412  -2.686  1.00  0.00           H  
HETATM   42  H19 UNL     1       6.453  -0.867  -3.168  1.00  0.00           H  
HETATM   43  H20 UNL     1       5.413  -2.799  -2.076  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.610  -2.488  -0.525  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.703  -0.208   2.514  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.459  -1.767   1.824  1.00  0.00           H  
HETATM   47  H24 UNL     1      -6.669  -2.781  -0.038  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9    9   10
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   15   19
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   44
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   22   23
CONECT   23   47
END

HMDB0259946
     RDKit          3D
Yakuchinone-A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.9583   -0.1508   -3.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6677   -0.8575   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209   -0.6981   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4297    0.1788   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1848    0.3416    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    1.2573    0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    0.4854    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351    1.4493    1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    2.4944    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928    1.1384    2.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.0627    2.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982   -0.1754    1.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.2152    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -0.3281   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527    0.7636   -1.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    0.5920   -2.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447   -0.6755   -2.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812   -1.7863   -1.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0379   -1.5876   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324   -0.3720    1.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.2273    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1492   -1.3953   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1396   -2.2695   -0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5529   -0.1937   -4.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -0.5826   -3.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602    0.9012   -3.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172    0.7546   -1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    1.6401    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    2.0355    0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    0.0431    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -0.2781    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.1412    3.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    2.0634    2.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3148   -1.0108    2.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -0.2013    3.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8048    0.5934    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.1425    1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643    0.6241    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419   -1.1406    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    1.7610   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6649    1.4116   -2.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526   -0.8673   -3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -2.7988   -2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101   -2.4875   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.2080    2.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4594   -1.7672    1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6689   -2.7813   -0.0375 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 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
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Yakuchinone-a	ChEBI
1-(4'-Hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone	MeSH

Chemical Formula

C₂₀H₂₄O₃

Average Molecular Weight

312.409

Monoisotopic Molecular Weight

312.172544633

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one

Traditional Name

1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC(=O)CCCCC2=CC=CC=C2)=CC=C1O

InChI Identifier

InChI=1S/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3

InChI Key

TXELARZTKDBEKS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Paradol
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:66033 )
monomethoxybenzene (CHEBI:66033 )
ketone (CHEBI:66033 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	4.6	ALOGPS
logP	5.09	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.49 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
AllCCS	[M+H]+	179.997	32859911
AllCCS	[M+H-H2O]+	176.507	32859911
AllCCS	[M+Na]+	184.165	32859911
AllCCS	[M+NH4]+	183.234	32859911
AllCCS	[M-H]-	182.002	32859911
AllCCS	[M+Na-2H]-	182.45	32859911
AllCCS	[M+HCOO]-	183.094	32859911
DeepCCS	[M+H]+	172.132	30932474
DeepCCS	[M-H]-	169.774	30932474
DeepCCS	[M-2H]-	203.118	30932474
DeepCCS	[M+Na]+	178.47	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Yakuchinone-A	COC1=CC(CCC(=O)CCCCC2=CC=CC=C2)=CC=C1O	3884.5	Standard polar	33892256
Yakuchinone-A	COC1=CC(CCC(=O)CCCCC2=CC=CC=C2)=CC=C1O	2499.4	Standard non polar	33892256
Yakuchinone-A	COC1=CC(CCC(=O)CCCCC2=CC=CC=C2)=CC=C1O	2644.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Yakuchinone-A,2TMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2774.6	Semi standard non polar	33892256
Yakuchinone-A,2TMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2622.1	Standard non polar	33892256
Yakuchinone-A,2TMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3042.1	Standard polar	33892256
Yakuchinone-A,2TMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2814.6	Semi standard non polar	33892256
Yakuchinone-A,2TMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2644.3	Standard non polar	33892256
Yakuchinone-A,2TMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3080.9	Standard polar	33892256
Yakuchinone-A,2TBDMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3224.3	Semi standard non polar	33892256
Yakuchinone-A,2TBDMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3026.7	Standard non polar	33892256
Yakuchinone-A,2TBDMS,isomer #1	COC1=CC(CCC(=CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3213.0	Standard polar	33892256
Yakuchinone-A,2TBDMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3303.5	Semi standard non polar	33892256
Yakuchinone-A,2TBDMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3066.5	Standard non polar	33892256
Yakuchinone-A,2TBDMS,isomer #2	COC1=CC(CC=C(CCCCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3258.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fa6-1910000000-36b5fa8e7064e64d432e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yakuchinone-A GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	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

117495

KEGG Compound ID

C20211

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66033

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486701

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 Yakuchinone-A (HMDB0259946)

MOL for HMDB0259946 (Yakuchinone-A)

3D MOL for HMDB0259946 (Yakuchinone-A)

3D SDF for HMDB0259946 (Yakuchinone-A)

3D-SDF for HMDB0259946 (Yakuchinone-A)

PDB for HMDB0259946 (Yakuchinone-A)

3D PDB for HMDB0259946 (Yakuchinone-A)

SMILES for HMDB0259946 (Yakuchinone-A)

INCHI for HMDB0259946 (Yakuchinone-A)

Structure for HMDB0259946 (Yakuchinone-A)

3D Structure for HMDB0259946 (Yakuchinone-A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra