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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:43:51 UTC

Update Date

2022-03-07 02:55:21 UTC

HMDB ID

HMDB0037479

Secondary Accession Numbers

HMDB37479

Metabolite Identification

Common Name

Xanthohumol

Description

Xanthohumol 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 is considered to be a flavonoid. Xanthohumol is a bitter tasting compound. Xanthohumol is found, on average, in the highest concentration within beer. Xanthohumol has also been detected, but not quantified in, alcoholic beverages. This could make xanthohumol a potential biomarker for the consumption of these foods. Xanthohumol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Xanthohumol.

Structure

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

  Mrv0541 02241218522D          

 26 27  0  0  0  0            999 V2000
    0.0041    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2 15  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  2  0  0  0  0
 14 20  1  0  0  0  0
 18 26  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0037479
     RDKit          3D
Xanthohumol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.4280    5.0201    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    3.7977    0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    2.6875    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.7162    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.6214   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0298    1.6915   -0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075    0.4464   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -0.7857   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -0.6515   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719   -1.3831   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190   -2.3668    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378   -1.2310   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    0.3964   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305   -0.7918   -0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227    1.4999    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.5193    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    2.5877    0.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4145    0.3920    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.4792    0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347   -0.6314    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0078   -0.4376    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9425   -1.4287    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -2.6781   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -3.6998   -0.4926 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094   -2.9087   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799   -1.8874   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    5.5400    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    5.6692    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    4.8811    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416    3.6559    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4995    2.5637    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.0511   -1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781   -1.5963    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162    0.0395   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674   -1.8131    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3928   -2.9425    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -3.1114    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9857   -1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9198   -0.5331    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508   -2.2271   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.5932   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.5813   -0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146    1.4356    0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3237    0.5562    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.2411    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1925   -4.6239   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919   -3.8942   -0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446   -2.1209   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 15  3  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
M  END

  Mrv0541 02241218522D          

 26 27  0  0  0  0            999 V2000
    0.0041    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2 15  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  2  0  0  0  0
 14 20  1  0  0  0  0
 18 26  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037479

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

> <INCHI_KEY>
ORXQGKIUCDPEAJ-YRNVUSSQSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.55185448619768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
5.200525077666667

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.71882399904212

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.647146199482834

> <JCHEM_PKA_STRONGEST_BASIC>
-4.896190778256668

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
103.5257

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthohumol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037479
     RDKit          3D
Xanthohumol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.4280    5.0201    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    3.7977    0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    2.6875    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.7162    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.6214   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0298    1.6915   -0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075    0.4464   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -0.7857   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -0.6515   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719   -1.3831   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190   -2.3668    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378   -1.2310   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    0.3964   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305   -0.7918   -0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227    1.4999    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.5193    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    2.5877    0.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4145    0.3920    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.4792    0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347   -0.6314    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0078   -0.4376    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9425   -1.4287    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -2.6781   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -3.6998   -0.4926 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094   -2.9087   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799   -1.8874   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    5.5400    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    5.6692    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    4.8811    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416    3.6559    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4995    2.5637    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.0511   -1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781   -1.5963    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162    0.0395   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674   -1.8131    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3928   -2.9425    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -3.1114    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9857   -1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9198   -0.5331    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508   -2.2271   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.5932   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.5813   -0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146    1.4356    0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3237    0.5562    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.2411    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1925   -4.6239   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919   -3.8942   -0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446   -2.1209   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 15  3  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.008   1.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.008  -0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.670  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.670   1.156   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.340   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.005  -1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.005  -2.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.338  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.667  -2.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.667  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.338  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.327   1.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.662   1.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.662  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.327  -1.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.340   3.465   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002  -3.465   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.340  -1.154   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.327   3.465   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.997  -1.154   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.997   1.924   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.332   1.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.667   1.924   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002   1.156   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.667   3.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.340  -2.694   0.000  0.00  0.00           C+0
CONECT    1    2    5   12                                                  
CONECT    2    1   15   18                                                  
CONECT    3    4    6                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4   16                                                  
CONECT    6    3    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10                                                       
CONECT   12    1   13   19                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15    2   14                                                       
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18    2   26                                                       
CONECT   19   12                                                            
CONECT   20   14                                                            
CONECT   21   13   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0037479
HETATM    1  C1  UNL     1      -0.428   5.020   1.269  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.167   3.798   0.966  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.564   2.687   0.550  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.923   2.716   0.408  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.653   1.621  -0.003  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.030   1.691  -0.135  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.007   0.446  -0.286  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.684  -0.786  -0.736  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.126  -0.651  -0.957  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.972  -1.383  -0.260  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.519  -2.367   0.772  1.00  0.00           C  
HETATM   12  C10 UNL     1      -6.438  -1.231  -0.502  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.620   0.396  -0.147  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.031  -0.792  -0.433  1.00  0.00           O  
HETATM   15  C12 UNL     1       0.123   1.500   0.268  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.549   1.519   0.432  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.116   2.588   0.817  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.415   0.392   0.187  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.740   0.479   0.359  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.635  -0.631   0.122  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.008  -0.438   0.329  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.942  -1.429   0.133  1.00  0.00           C  
HETATM   23  C19 UNL     1       6.549  -2.678  -0.284  1.00  0.00           C  
HETATM   24  O5  UNL     1       7.457  -3.700  -0.493  1.00  0.00           O  
HETATM   25  C20 UNL     1       5.209  -2.909  -0.498  1.00  0.00           C  
HETATM   26  C21 UNL     1       4.280  -1.887  -0.293  1.00  0.00           C  
HETATM   27  H1  UNL     1      -0.711   5.540   0.327  1.00  0.00           H  
HETATM   28  H2  UNL     1       0.312   5.669   1.784  1.00  0.00           H  
HETATM   29  H3  UNL     1      -1.358   4.881   1.854  1.00  0.00           H  
HETATM   30  H4  UNL     1      -2.442   3.656   0.634  1.00  0.00           H  
HETATM   31  H5  UNL     1      -4.500   2.564   0.076  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.228  -1.051  -1.736  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.478  -1.596   0.003  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.516   0.040  -1.690  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.067  -1.813   1.631  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.393  -2.943   1.132  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.808  -3.111   0.357  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.566  -0.986  -1.579  1.00  0.00           H  
HETATM   39  H13 UNL     1      -6.920  -0.533   0.182  1.00  0.00           H  
HETATM   40  H14 UNL     1      -6.951  -2.227  -0.363  1.00  0.00           H  
HETATM   41  H15 UNL     1      -0.492  -1.593  -0.733  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.092  -0.581  -0.142  1.00  0.00           H  
HETATM   43  H17 UNL     1       4.115   1.436   0.689  1.00  0.00           H  
HETATM   44  H18 UNL     1       6.324   0.556   0.661  1.00  0.00           H  
HETATM   45  H19 UNL     1       8.002  -1.241   0.304  1.00  0.00           H  
HETATM   46  H20 UNL     1       7.192  -4.624  -0.799  1.00  0.00           H  
HETATM   47  H21 UNL     1       4.892  -3.894  -0.828  1.00  0.00           H  
HETATM   48  H22 UNL     1       3.245  -2.121  -0.474  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   30
CONECT    5    6    7    7
CONECT    6   31
CONECT    7    8   13
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   12
CONECT   11   35   36   37
CONECT   12   38   39   40
CONECT   13   14   15   15
CONECT   14   41
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   26
CONECT   21   22   44
CONECT   22   23   23   45
CONECT   23   24   25
CONECT   24   46
CONECT   25   26   26   47
CONECT   26   48
END

HMDB0037479
     RDKit          3D
Xanthohumol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.4280    5.0201    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    3.7977    0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    2.6875    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.7162    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.6214   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0298    1.6915   -0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075    0.4464   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -0.7857   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -0.6515   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719   -1.3831   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5190   -2.3668    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378   -1.2310   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    0.3964   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305   -0.7918   -0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1227    1.4999    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.5193    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    2.5877    0.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4145    0.3920    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.4792    0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347   -0.6314    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0078   -0.4376    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9425   -1.4287    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -2.6781   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -3.6998   -0.4926 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094   -2.9087   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799   -1.8874   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    5.5400    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    5.6692    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    4.8811    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416    3.6559    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4995    2.5637    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.0511   -1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781   -1.5963    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162    0.0395   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674   -1.8131    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3928   -2.9425    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -3.1114    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -0.9857   -1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9198   -0.5331    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508   -2.2271   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.5932   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.5813   -0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146    1.4356    0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3237    0.5562    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.2411    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1925   -4.6239   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919   -3.8942   -0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446   -2.1209   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 15  3  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone	ChEBI
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one	Kegg
Desmethylxanthohumol	MeSH
1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	MeSH

Chemical Formula

C₂₁H₂₂O₅

Average Molecular Weight

354.3964

Monoisotopic Molecular Weight

354.146723814

IUPAC Name

(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

xanthohumol

CAS Registry Number

6754-58-1

SMILES

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

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

InChI Key

ORXQGKIUCDPEAJ-YRNVUSSQSA-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
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
Anisole
Methoxybenzene
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
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

aromatic ether (CHEBI:66331 )
polyphenol (CHEBI:66331 )
chalcones (CHEBI:66331 )
chalcones (C16417 )
Chalcones and dihydrochalcones (C16417 )
Chalcones and dihydrochalcones (LMPK12120294 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037479)
Cell membrane (HMDB: HMDB0037479)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037479)

Source

Exogenous

Exogenous (HMDB: HMDB0037479)

Food

Food (HMDB: HMDB0037479)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0037479)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiviral

Antiviral (HMDB: HMDB0037479)

Biological role

Nutrient (HMDB: HMDB0037479)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 °C	Not Available
Boiling Point	576.00 to 577.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.51 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.172 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	3.91	ALOGPS
logP	5.2	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-4.9	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	6	ChemAxon
Refractivity	103.53 m³·mol⁻¹	ChemAxon
Polarizability	38.55 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
DeepCCS	[M+H]+	193.599	30932474
DeepCCS	[M-H]-	191.241	30932474
DeepCCS	[M-2H]-	224.792	30932474
DeepCCS	[M+Na]+	200.02	30932474
AllCCS	[M+H]+	187.8	32859911
AllCCS	[M+H-H2O]+	184.6	32859911
AllCCS	[M+NH4]+	190.8	32859911
AllCCS	[M+Na]+	191.6	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1	5040.4	Standard polar	33892256
Xanthohumol	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1	3054.5	Standard non polar	33892256
Xanthohumol	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1	3372.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol,1TMS,isomer #1	COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3203.7	Semi standard non polar	33892256
Xanthohumol,1TMS,isomer #2	COC1=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3231.6	Semi standard non polar	33892256
Xanthohumol,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3193.3	Semi standard non polar	33892256
Xanthohumol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3147.7	Semi standard non polar	33892256
Xanthohumol,2TMS,isomer #2	COC1=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3157.9	Semi standard non polar	33892256
Xanthohumol,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3149.7	Semi standard non polar	33892256
Xanthohumol,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	3173.8	Semi standard non polar	33892256
Xanthohumol,1TBDMS,isomer #1	COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3463.8	Semi standard non polar	33892256
Xanthohumol,1TBDMS,isomer #2	COC1=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3504.4	Semi standard non polar	33892256
Xanthohumol,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3444.9	Semi standard non polar	33892256
Xanthohumol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3686.6	Semi standard non polar	33892256
Xanthohumol,2TBDMS,isomer #2	COC1=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3703.3	Semi standard non polar	33892256
Xanthohumol,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3672.0	Semi standard non polar	33892256
Xanthohumol,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3900.6	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-3359000000-513a171f819b95432ac8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2131390000-01a52cd1365880409310	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol ESI-TOF , Negative-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol ESI-TOF 20V, Negative-QTOF	splash10-014i-0940000000-46dc70d70ca70dcf01b4	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol ESI-TOF , Negative-QTOF	splash10-0udi-0009000000-adffe3727a9d190af9ea	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol ESI-TOF 20V, Negative-QTOF	splash10-0ue9-0159000000-89390bf396bc026f25db	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , negative-QTOF	splash10-0udi-0029000000-5292b3ba1142d29c7386	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , negative-QTOF	splash10-0ue9-0497000000-dec7e1db8ee3c405c5da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , negative-QTOF	splash10-0159-0981000000-c78fd55b14d98033f180	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-TOF , negative-QTOF	splash10-0ue9-0159000000-89390bf396bc026f25db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol , negative-QTOF	splash10-0uxr-0978000000-bb0b197988e97a4a05ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , positive-QTOF	splash10-004j-0970000000-179d5086107c87523593	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , positive-QTOF	splash10-004i-0910000000-2dea6c7222209825ac37	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QQ , positive-QTOF	splash10-004i-0900000000-4e1106c364aad0846401	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QTOF , positive-QTOF	splash10-0002-0293000000-07b3d1d40f210eb9247b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QTOF , positive-QTOF	splash10-004i-0940000000-6983981e47a0f6af296b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-cee69c093feb8d9b8aa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-ITFT , positive-QTOF	splash10-0002-0190000000-ec80f253f42d34e79be9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-ITFT , positive-QTOF	splash10-0002-0190000000-c3d920598c6526bdb0ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-ITFT , positive-QTOF	splash10-0002-0290000000-a3b357466ef6c20fc37d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthohumol LC-ESI-ITFT , positive-QTOF	splash10-0002-0290000000-a6fb7803116d7827f288	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 10V, Positive-QTOF	splash10-0a4i-0129000000-6cc3dfff7ce5ef42566f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 20V, Positive-QTOF	splash10-05mt-3596000000-0fb44a4b969d525ddeb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 40V, Positive-QTOF	splash10-014i-4910000000-c8ee4088761d3e104636	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 10V, Negative-QTOF	splash10-0udi-0129000000-d3c87e511f6c42141ff1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 20V, Negative-QTOF	splash10-0pbd-0965000000-856a6ce55c4795d014f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol 40V, Negative-QTOF	splash10-0aba-1920000000-72db9ec75d5e130d0a45	2016-08-03	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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Xanthohumol

METLIN ID

Not Available

PubChem Compound

639665

PDB ID

Not Available

ChEBI ID

66331

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1500861

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Buckwold VE, Wilson RJ, Nalca A, Beer BB, Voss TG, Turpin JA, Buckheit RW 3rd, Wei J, Wenzel-Mathers M, Walton EM, Smith RJ, Pallansch M, Ward P, Wells J, Chuvala L, Sloane S, Paulman R, Russell J, Hartman T, Ptak R: Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral Res. 2004 Jan;61(1):57-62. [PubMed:14670594 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Xanthohumol (HMDB0037479)

MOL for HMDB0037479 (Xanthohumol)

3D MOL for HMDB0037479 (Xanthohumol)

3D SDF for HMDB0037479 (Xanthohumol)

3D-SDF for HMDB0037479 (Xanthohumol)

PDB for HMDB0037479 (Xanthohumol)

3D PDB for HMDB0037479 (Xanthohumol)

SMILES for HMDB0037479 (Xanthohumol)

INCHI for HMDB0037479 (Xanthohumol)

Structure for HMDB0037479 (Xanthohumol)

3D Structure for HMDB0037479 (Xanthohumol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra