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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:44:14 UTC

Update Date

2022-03-07 02:55:21 UTC

HMDB ID

HMDB0037485

Secondary Accession Numbers

HMDB37485

Metabolite Identification

Common Name

Stercurensin

Description

Stercurensin belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, stercurensin is considered to be a flavonoid. Stercurensin 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 significant number of articles have been published on Stercurensin.

Structure

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

HMDB0037485
     RDKit          3D
Stercurensin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7729    2.9659   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.5952   -0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    0.7343   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542    1.2682   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0864    0.4862   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    1.0242   -0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.8347   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -1.6928    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.4485    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -2.7790    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.6050    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -1.1879    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.4355    0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.4778    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.1599    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.5120    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005    0.7998    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116    1.2928    0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1023    0.4978    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -0.8321    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5559   -1.3390    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    3.5476   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    3.1302   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    3.4133    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082    2.3184   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    2.0176   -0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5823   -1.6882   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541   -1.1910    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -2.6946    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -3.3827    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1515    0.5707    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.2108    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.4665    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.3558    0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    0.9047    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631   -1.5115    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724   -2.4061    1.0872 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
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv0541 05061309482D          

 21 22  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    2.8579    7.4250    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037485

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-11-14(19)10-15(21-2)16(17(11)20)13(18)9-8-12-6-4-3-5-7-12/h3-10,19-20H,1-2H3/b9-8+

> <INCHI_KEY>
JUZVHLGKYJTCKP-CMDGGOBGSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.383007711253413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.288944789333333

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.427628877945073

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.223800043226133

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884649367568723

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.34319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stercurensin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037485
     RDKit          3D
Stercurensin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7729    2.9659   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.5952   -0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    0.7343   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542    1.2682   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0864    0.4862   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    1.0242   -0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.8347   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -1.6928    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.4485    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -2.7790    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.6050    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -1.1879    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.4355    0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.4778    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.1599    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.5120    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005    0.7998    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116    1.2928    0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1023    0.4978    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -0.8321    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5559   -1.3390    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    3.5476   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    3.1302   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    3.4133    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082    2.3184   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    2.0176   -0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5823   -1.6882   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541   -1.1910    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -2.6946    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -3.3827    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1515    0.5707    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.2108    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.4665    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.3558    0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    0.9047    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631   -1.5115    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724   -2.4061    1.0872 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
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10   14   15                                                       
CONECT   11    1   14   17                                                  
CONECT   12    6    7    8                                                  
CONECT   13    9   16   18                                                  
CONECT   14   10   11   19                                                  
CONECT   15   10   16   21                                                  
CONECT   16   13   15   17                                                  
CONECT   17   11   16   20                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   17                                                            
CONECT   21    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0037485
HETATM    1  C1  UNL     1      -0.773   2.966  -0.512  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.603   1.595  -0.216  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.684   0.734  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.954   1.268  -0.381  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.086   0.486  -0.334  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.349   1.024  -0.568  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.921  -0.835  -0.049  1.00  0.00           C  
HETATM    8  C6  UNL     1      -5.126  -1.693   0.006  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.683  -1.448   0.198  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.682  -2.779   0.468  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.560  -0.605   0.137  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.240  -1.188   0.385  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.159  -2.435   0.647  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.020  -0.478   0.365  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.148  -1.160   0.615  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.471  -0.512   0.614  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.701   0.800   0.370  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.012   1.293   0.399  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.102   0.498   0.668  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.833  -0.832   0.911  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.556  -1.339   0.889  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.142   3.548  -0.419  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.242   3.130  -1.503  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.501   3.413   0.228  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.008   2.318  -0.600  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.420   2.018  -0.777  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.582  -1.688  -1.017  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.854  -1.191   0.699  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.935  -2.695   0.389  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.973  -3.383   0.661  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.152   0.571   0.165  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.048  -2.211   0.819  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.877   1.467   0.153  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.138   2.356   0.195  1.00  0.00           H  
HETATM   35  H14 UNL     1       7.102   0.905   0.684  1.00  0.00           H  
HETATM   36  H15 UNL     1       6.663  -1.511   1.131  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.372  -2.406   1.087  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8    9
CONECT    8   27   28   29
CONECT    9   10   11   11
CONECT   10   30
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   21
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0037485
     RDKit          3D
Stercurensin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7729    2.9659   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.5952   -0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    0.7343   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542    1.2682   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0864    0.4862   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    1.0242   -0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.8347   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259   -1.6928    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.4485    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -2.7790    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -0.6050    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -1.1879    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.4355    0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.4778    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.1599    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.5120    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005    0.7998    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116    1.2928    0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1023    0.4978    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -0.8321    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5559   -1.3390    0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    3.5476   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    3.1302   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    3.4133    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082    2.3184   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    2.0176   -0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5823   -1.6882   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541   -1.1910    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -2.6946    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -3.3827    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1515    0.5707    0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.2108    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.4665    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.3558    0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    0.9047    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631   -1.5115    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724   -2.4061    1.0872 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
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2,4-Dihydroxy-6-methoxy-3-methylphenyl)-3-phenyl-2-propen-1-one	HMDB
2',4'-Dihydroxy-6'-methoxy-3'-methylchalcone	HMDB

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

(2E)-1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-3-phenylprop-2-en-1-one

Traditional Name

stercurensin

CAS Registry Number

94388-75-7

SMILES

COC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C1

InChI Identifier

InChI=1S/C17H16O4/c1-11-14(19)10-15(21-2)16(17(11)20)13(18)9-8-12-6-4-3-5-7-12/h3-10,19-20H,1-2H3/b9-8+

InChI Key

JUZVHLGKYJTCKP-CMDGGOBGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Methoxyphenol
O-cresol
Phenol ether
Resorcinol
Styrene
Phenoxy compound
Aryl ketone
Benzoyl
Anisole
Methoxybenzene
Toluene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:70659 )
monomethoxybenzene (CHEBI:70659 )
chalcones (CHEBI:70659 )
Chalcones and dihydrochalcones (LMPK12120223 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037485)
Cell membrane (HMDB: HMDB0037485)

Source

Exogenous

Exogenous (HMDB: HMDB0037485)

Food

Food (HMDB: HMDB0037485)

Endogenous

Plant

Plant (HMDB: HMDB0037485)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037485)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 211 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.64	ALOGPS
logP	4.29	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.34 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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]+	172.807	30932474
DeepCCS	[M-H]-	170.449	30932474
DeepCCS	[M-2H]-	203.799	30932474
DeepCCS	[M+Na]+	179.026	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	167.6	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.31 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1532 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2854.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	435.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	804.9 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	898.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1550.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	584.7 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	1580.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	482.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	541.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	275.0 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	21.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Stercurensin	COC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C1	4180.9	Standard polar	33892256
Stercurensin	COC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C1	2594.3	Standard non polar	33892256
Stercurensin	COC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C1	2733.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Stercurensin,1TMS,isomer #1	COC1=CC(O)=C(C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=CC=C1	2571.6	Semi standard non polar	33892256
Stercurensin,1TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C(C)C(O)=C1C(=O)/C=C/C1=CC=CC=C1	2570.4	Semi standard non polar	33892256
Stercurensin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=CC=C1	2597.1	Semi standard non polar	33892256
Stercurensin,1TBDMS,isomer #1	COC1=CC(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=CC=C1	2828.8	Semi standard non polar	33892256
Stercurensin,1TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C1C(=O)/C=C/C1=CC=CC=C1	2856.3	Semi standard non polar	33892256
Stercurensin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=CC=C1	3118.5	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 - Stercurensin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-3790000000-6db5e18cce89a87da1ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stercurensin GC-MS (2 TMS) - 70eV, Positive	splash10-03e9-5918700000-9050d7d9791c630a16f2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stercurensin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stercurensin 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 - Stercurensin 10V, Positive-QTOF	splash10-000i-0290000000-768c9ab903fd629d1c54	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 20V, Positive-QTOF	splash10-001r-1970000000-7f95194457a4a11ead0c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 40V, Positive-QTOF	splash10-0zmi-2900000000-6b47cca91ac257d56e57	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 10V, Negative-QTOF	splash10-001i-0390000000-81a5e886d4cb22131892	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 20V, Negative-QTOF	splash10-0ue9-0930000000-814eae7c7d7bbae096e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 40V, Negative-QTOF	splash10-066r-5900000000-d36a7bb4e769d657562e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 10V, Positive-QTOF	splash10-000i-0190000000-64bf024069bb61f75e1e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 20V, Positive-QTOF	splash10-0f89-0910000000-6498ed3d580a3cc2ab86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 40V, Positive-QTOF	splash10-0ufr-2910000000-d890ed20e3b05a683f52	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 10V, Negative-QTOF	splash10-001i-0290000000-ee4d7641f0da96625863	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 20V, Negative-QTOF	splash10-0f89-0940000000-0a1cfb3c5d60c65b114e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stercurensin 40V, Negative-QTOF	splash10-005j-5920000000-77cf15b9e161b650a700	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016556

KNApSAcK ID

C00007042

Chemspider ID

9953283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11778601

PDB ID

Not Available

ChEBI ID

70659

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1861471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim YJ, Kim HC, Ko H, Amor EC, Lee JW, Yang HO: Stercurensin inhibits nuclear factor-kappaB-dependent inflammatory signals through attenuation of TAK1-TAB1 complex formation. J Cell Biochem. 2011 Feb;112(2):548-58. doi: 10.1002/jcb.22945. [PubMed:21268076 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Stercurensin (HMDB0037485)

MOL for HMDB0037485 (Stercurensin)

3D MOL for HMDB0037485 (Stercurensin)

3D SDF for HMDB0037485 (Stercurensin)

3D-SDF for HMDB0037485 (Stercurensin)

PDB for HMDB0037485 (Stercurensin)

3D PDB for HMDB0037485 (Stercurensin)

SMILES for HMDB0037485 (Stercurensin)

INCHI for HMDB0037485 (Stercurensin)

Structure for HMDB0037485 (Stercurensin)

3D Structure for HMDB0037485 (Stercurensin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra