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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:50:43 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034917

Secondary Accession Numbers

HMDB34917

Metabolite Identification

Common Name

Xanthohumol E

Description

Xanthohumol E belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, xanthohumol e is considered to be a flavonoid. Xanthohumol E has been detected, but not quantified in, alcoholic beverages. This could make xanthohumol e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthohumol E.

Structure

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


  Mrv0541 05061308082D          

 30 32  0  0  0  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 14 13  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  5  2  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 12  1  0  0  0  0
 21 20  1  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24 19  2  0  0  0  0
 24 21  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
M  END

HMDB0034917
     RDKit          3D
Xanthohumol E
 56 58  0  0  0  0  0  0  0  0999 V2000
   -5.4917   -2.5332    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881   -2.6622   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278   -3.1104   -2.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -2.3972   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -1.9512    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -0.6665    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    0.5386    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.4723    0.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0058    1.7496    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7588    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    0.5836    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6807    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294    1.8859    0.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -0.4129    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062   -0.1214    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -1.1526    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1742   -0.7867    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1833   -1.7205    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8930   -3.0764    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9087   -4.0184    0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -3.4545    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535   -2.4871    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804   -0.5984    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -1.7687    0.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062    2.9838    0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    4.2344    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    5.1571    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    4.9349   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    4.1520    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    3.0115    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1673   -2.8934    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8699   -1.4912    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -3.1189   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8203   -3.7358   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.2221   -2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -3.7428   -2.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -2.5031   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688   -1.7144    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503   -2.7319    1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093    1.2581    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.4330    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    0.9457    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2657    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2284   -1.4071    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2196   -4.3901   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058   -4.5014    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312   -2.8452    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -2.6627    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296    5.5968    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778    6.0129    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.6391    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    6.0147   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    4.4752   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764    4.8153   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6230    5.1095    0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    3.0350    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 19 21  1  0
 21 22  2  0
 11 23  2  0
 23 24  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  2  0
 23  6  1  0
 30  9  1  0
 22 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
M  END


  Mrv0541 05061308082D          

 30 32  0  0  0  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 14 13  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  5  2  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 12  1  0  0  0  0
 21 20  1  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24 19  2  0  0  0  0
 24 21  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034917

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+

> <INCHI_KEY>
KRZGSPKDWYNTHE-XYOKQWHBSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.4709

> <EXACT_MASS>
406.178023942

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.51940224211968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-2H-chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
6.2588197453333345

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.74459310092228

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.637166317120107

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9736353788410925

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
121.45589999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthohumol E

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034917
     RDKit          3D
Xanthohumol E
 56 58  0  0  0  0  0  0  0  0999 V2000
   -5.4917   -2.5332    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881   -2.6622   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278   -3.1104   -2.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -2.3972   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -1.9512    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -0.6665    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    0.5386    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.4723    0.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0058    1.7496    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7588    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    0.5836    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6807    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294    1.8859    0.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -0.4129    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062   -0.1214    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -1.1526    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1742   -0.7867    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1833   -1.7205    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8930   -3.0764    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9087   -4.0184    0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -3.4545    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535   -2.4871    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804   -0.5984    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -1.7687    0.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062    2.9838    0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    4.2344    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    5.1571    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    4.9349   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    4.1520    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    3.0115    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1673   -2.8934    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8699   -1.4912    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -3.1189   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8203   -3.7358   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.2221   -2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -3.7428   -2.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -2.5031   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688   -1.7144    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503   -2.7319    1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093    1.2581    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.4330    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    0.9457    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2657    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2284   -1.4071    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2196   -4.3901   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058   -4.5014    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312   -2.8452    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -2.6627    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296    5.5968    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778    6.0129    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.6391    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    6.0147   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    4.4752   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764    4.8153   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6230    5.1095    0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    3.0350    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 19 21  1  0
 21 22  2  0
 11 23  2  0
 23 24  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  2  0
 23  6  1  0
 30  9  1  0
 22 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  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      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151   0.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.141  -1.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5   11   15                                                       
CONECT    6    9   16                                                       
CONECT    7   10   16                                                       
CONECT    8   12   16                                                       
CONECT    9    6   17                                                       
CONECT   10    7   17                                                       
CONECT   11    5   18                                                       
CONECT   12    8   20                                                       
CONECT   13   14   19                                                       
CONECT   14   13   25                                                       
CONECT   15    1    2    5                                                  
CONECT   16    6    7    8                                                  
CONECT   17    9   10   26                                                  
CONECT   18   11   22   23                                                  
CONECT   19   13   22   24                                                  
CONECT   20   12   21   27                                                  
CONECT   21   20   23   24                                                  
CONECT   22   18   19   28                                                  
CONECT   23   18   21   29                                                  
CONECT   24   19   21   30                                                  
CONECT   25    3    4   14   30                                             
CONECT   26   17                                                            
CONECT   27   20                                                            
CONECT   28   22                                                            
CONECT   29   23                                                            
CONECT   30   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0034917
HETATM    1  C1  UNL     1      -5.492  -2.533   0.119  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.488  -2.662  -0.948  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.928  -3.110  -2.296  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.227  -2.397  -0.745  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.714  -1.951   0.554  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.957  -0.666   0.462  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.653   0.539   0.401  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.017   0.472   0.442  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.006   1.750   0.304  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.635   1.759   0.266  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.124   0.584   0.322  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.566   0.681   0.268  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.029   1.886   0.180  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.517  -0.413   0.300  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.806  -0.121   0.237  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.824  -1.153   0.263  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.174  -0.787   0.193  1.00  0.00           C  
HETATM   18  C16 UNL     1       7.183  -1.720   0.212  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.893  -3.076   0.302  1.00  0.00           C  
HETATM   20  O3  UNL     1       7.909  -4.018   0.322  1.00  0.00           O  
HETATM   21  C18 UNL     1       5.573  -3.454   0.371  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.554  -2.487   0.351  1.00  0.00           C  
HETATM   23  C20 UNL     1      -0.580  -0.598   0.419  1.00  0.00           C  
HETATM   24  O4  UNL     1       0.110  -1.769   0.475  1.00  0.00           O  
HETATM   25  O5  UNL     1      -0.006   2.984   0.168  1.00  0.00           O  
HETATM   26  C21 UNL     1      -0.617   4.234   0.101  1.00  0.00           C  
HETATM   27  C22 UNL     1      -0.178   5.157   1.239  1.00  0.00           C  
HETATM   28  C23 UNL     1      -0.261   4.935  -1.213  1.00  0.00           C  
HETATM   29  C24 UNL     1      -2.087   4.152   0.147  1.00  0.00           C  
HETATM   30  C25 UNL     1      -2.720   3.011   0.240  1.00  0.00           C  
HETATM   31  H1  UNL     1      -5.167  -2.893   1.116  1.00  0.00           H  
HETATM   32  H2  UNL     1      -5.870  -1.491   0.240  1.00  0.00           H  
HETATM   33  H3  UNL     1      -6.410  -3.119  -0.144  1.00  0.00           H  
HETATM   34  H4  UNL     1      -5.820  -3.736  -2.187  1.00  0.00           H  
HETATM   35  H5  UNL     1      -5.073  -2.222  -2.955  1.00  0.00           H  
HETATM   36  H6  UNL     1      -4.088  -3.743  -2.698  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.499  -2.503  -1.561  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.569  -1.714   1.262  1.00  0.00           H  
HETATM   39  H9  UNL     1      -2.150  -2.732   1.085  1.00  0.00           H  
HETATM   40  H10 UNL     1      -4.609   1.258   0.406  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.220  -1.433   0.373  1.00  0.00           H  
HETATM   42  H12 UNL     1       4.104   0.946   0.161  1.00  0.00           H  
HETATM   43  H13 UNL     1       6.379   0.266   0.122  1.00  0.00           H  
HETATM   44  H14 UNL     1       8.228  -1.407   0.156  1.00  0.00           H  
HETATM   45  H15 UNL     1       8.220  -4.390  -0.585  1.00  0.00           H  
HETATM   46  H16 UNL     1       5.306  -4.501   0.442  1.00  0.00           H  
HETATM   47  H17 UNL     1       3.531  -2.845   0.409  1.00  0.00           H  
HETATM   48  H18 UNL     1      -0.310  -2.663   0.534  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.830   5.597   1.039  1.00  0.00           H  
HETATM   50  H20 UNL     1      -0.878   6.013   1.322  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.192   4.639   2.210  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.042   6.015  -1.031  1.00  0.00           H  
HETATM   53  H23 UNL     1       0.663   4.475  -1.586  1.00  0.00           H  
HETATM   54  H24 UNL     1      -1.076   4.815  -1.953  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.623   5.109   0.098  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.801   3.035   0.268  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   40
CONECT    9   10   10   30
CONECT   10   11   25
CONECT   11   12   23   23
CONECT   12   13   13   14
CONECT   14   15   15   41
CONECT   15   16   42
CONECT   16   17   17   22
CONECT   17   18   43
CONECT   18   19   19   44
CONECT   19   20   21
CONECT   20   45
CONECT   21   22   22   46
CONECT   22   47
CONECT   23   24
CONECT   24   48
CONECT   25   26
CONECT   26   27   28   29
CONECT   27   49   50   51
CONECT   28   52   53   54
CONECT   29   30   30   55
CONECT   30   56
END

HMDB0034917
     RDKit          3D
Xanthohumol E
 56 58  0  0  0  0  0  0  0  0999 V2000
   -5.4917   -2.5332    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881   -2.6622   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278   -3.1104   -2.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -2.3972   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -1.9512    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -0.6665    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    0.5386    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.4723    0.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0058    1.7496    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7588    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1237    0.5836    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6807    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294    1.8859    0.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -0.4129    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062   -0.1214    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -1.1526    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1742   -0.7867    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1833   -1.7205    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8930   -3.0764    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9087   -4.0184    0.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -3.4545    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535   -2.4871    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804   -0.5984    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -1.7687    0.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062    2.9838    0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    4.2344    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    5.1571    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    4.9349   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    4.1520    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    3.0115    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1673   -2.8934    1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8699   -1.4912    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -3.1189   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8203   -3.7358   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.2221   -2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -3.7428   -2.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -2.5031   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688   -1.7144    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503   -2.7319    1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093    1.2581    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.4330    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    0.9457    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2657    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2284   -1.4071    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2196   -4.3901   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058   -4.5014    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312   -2.8452    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -2.6627    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296    5.5968    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778    6.0129    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.6391    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    6.0147   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    4.4752   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764    4.8153   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6230    5.1095    0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    3.0350    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 19 21  1  0
 21 22  2  0
 11 23  2  0
 23 24  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  2  0
 23  6  1  0
 30  9  1  0
 22 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₅

Average Molecular Weight

406.4709

Monoisotopic Molecular Weight

406.178023942

IUPAC Name

(2E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-2H-chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

xanthohumol E

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+

InChI Key

KRZGSPKDWYNTHE-XYOKQWHBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Hydroxycinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Styrene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120263 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034917)

Cellular substructure

Membrane (HMDB: HMDB0034917)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034917)

Source

Exogenous

Food

Food (HMDB: HMDB0034917)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0034917)

Not Available

Nutrient (HMDB: HMDB0034917)

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
Water Solubility	0.0076 g/L	ALOGPS
logP	4.51	ALOGPS
logP	6.26	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.46 m³·mol⁻¹	ChemAxon
Polarizability	45.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	195.542	30932474
DeepCCS	[M-H]-	193.147	30932474
DeepCCS	[M-2H]-	226.597	30932474
DeepCCS	[M+Na]+	201.768	30932474
AllCCS	[M+H]+	201.6	32859911
AllCCS	[M+H-H2O]+	198.8	32859911
AllCCS	[M+NH4]+	204.1	32859911
AllCCS	[M+Na]+	204.9	32859911
AllCCS	[M-H]-	199.5	32859911
AllCCS	[M+Na-2H]-	199.5	32859911
AllCCS	[M+HCOO]-	199.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol E	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O	4765.4	Standard polar	33892256
Xanthohumol E	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O	3372.2	Standard non polar	33892256
Xanthohumol E	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O	3536.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol E,1TMS,isomer #1	CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C	3394.0	Semi standard non polar	33892256
Xanthohumol E,1TMS,isomer #2	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3399.4	Semi standard non polar	33892256
Xanthohumol E,1TMS,isomer #3	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3452.5	Semi standard non polar	33892256
Xanthohumol E,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3379.8	Semi standard non polar	33892256
Xanthohumol E,2TMS,isomer #2	CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C	3349.0	Semi standard non polar	33892256
Xanthohumol E,2TMS,isomer #3	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3362.5	Semi standard non polar	33892256
Xanthohumol E,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3386.9	Semi standard non polar	33892256
Xanthohumol E,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C(C)(C)C	3640.4	Semi standard non polar	33892256
Xanthohumol E,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3646.1	Semi standard non polar	33892256
Xanthohumol E,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3706.6	Semi standard non polar	33892256
Xanthohumol E,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3881.4	Semi standard non polar	33892256
Xanthohumol E,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C(C)(C)C	3892.1	Semi standard non polar	33892256
Xanthohumol E,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	3876.8	Semi standard non polar	33892256
Xanthohumol E,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C	4084.7	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 - Xanthohumol E GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3419000000-6b57ba67f36b750282ff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol E GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2100039000-e2df2595710013827aed	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol E 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 - Xanthohumol E 10V, Positive-QTOF	splash10-0a4i-1228900000-be84c08d3627bfb84386	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Positive-QTOF	splash10-05mt-3449100000-1308efc4968142069b76	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Positive-QTOF	splash10-066r-7693000000-f36e5b6f6382d4fc2afb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Negative-QTOF	splash10-0a4i-0131900000-510a93d327c759852a6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Negative-QTOF	splash10-0a4i-0692300000-e75638ba22e4a154b3cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Negative-QTOF	splash10-00bd-0952000000-b5d65dccff1b1660516f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Positive-QTOF	splash10-0udi-0009300000-8744eba2a46dd5076742	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Positive-QTOF	splash10-001i-0094200000-e4eac9c491fed44bc73d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Positive-QTOF	splash10-00ls-0189000000-3dce236f23c346862e80	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Negative-QTOF	splash10-0a4i-0000900000-7b5974fd53d3ffdb29ad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Negative-QTOF	splash10-0a4i-0163900000-1b15da60ece2daff6787	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Negative-QTOF	splash10-014i-5973000000-d1f27b7331f17adc1166	2021-09-25	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

FDB013502

KNApSAcK ID

C00014474

Chemspider ID

24845983

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245324

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

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

Showing metabocard for Xanthohumol E (HMDB0034917)

MOL for HMDB0034917 (Xanthohumol E)

3D MOL for HMDB0034917 (Xanthohumol E)

3D SDF for HMDB0034917 (Xanthohumol E)

3D-SDF for HMDB0034917 (Xanthohumol E)

PDB for HMDB0034917 (Xanthohumol E)

3D PDB for HMDB0034917 (Xanthohumol E)

SMILES for HMDB0034917 (Xanthohumol E)

INCHI for HMDB0034917 (Xanthohumol E)

Structure for HMDB0034917 (Xanthohumol E)

3D Structure for HMDB0034917 (Xanthohumol E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra