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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:56:28 UTC

Update Date

2022-03-07 02:54:19 UTC

HMDB ID

HMDB0035002

Secondary Accession Numbers

HMDB35002

Metabolite Identification

Common Name

Xanthogalenol

Description

Xanthogalenol 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, xanthogalenol is considered to be a flavonoid. Xanthogalenol has been detected, but not quantified in, alcoholic beverages. This could make xanthogalenol a potential biomarker for the consumption of these foods. Xanthogalenol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Xanthogalenol.

Structure

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


  Mrv0541 05061308112D          

 26 27  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    1.4289   -2.4750    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.1434   -2.8875    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

HMDB0035002
     RDKit          3D
Xanthogalenol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.1872   -3.4385   -2.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3753   -2.3816   -1.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065   -1.6995   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454   -2.0708   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463   -1.4112   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010   -1.8554   -0.8467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1291   -0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.3114    1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    1.2693    1.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    0.0317    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    0.7497    1.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7558    0.5037    1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763   -0.4503    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470   -0.6281    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508    0.1503    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9377   -0.0186    0.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366    1.1075    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    1.2955    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231   -0.0210    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.9786    1.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -0.6791    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -0.2919    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.4622   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    1.6953   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.3797    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    2.4006   -1.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496   -3.8071   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -4.2703   -1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -3.0415   -2.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -2.8784   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -2.5959   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.7223    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    1.5332    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976   -1.1069   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0052   -1.3954   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3590    0.5331   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7521    1.7419    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078    2.0698    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190    1.6309    2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.1970    0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535    0.3002    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -0.0786   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5679    1.7686    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.4786    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4633    3.3736    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468    2.1352   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    3.4857   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5585    2.0246   -1.8673 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  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  3  1  0
 18 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
M  END


  Mrv0541 05061308112D          

 26 27  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    1.4289   -2.4750    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.1434   -2.8875    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035002

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)4-10-16-19(26-3)12-18(24)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>
ALGFNVZQNNGHPA-YRNVUSSQSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.85067021880515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
5.850525077666667

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.820043791179547

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.817824577787964

> <JCHEM_PKA_STRONGEST_BASIC>
-4.868078789256216

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
103.52569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthogalenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035002
     RDKit          3D
Xanthogalenol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.1872   -3.4385   -2.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3753   -2.3816   -1.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065   -1.6995   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454   -2.0708   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463   -1.4112   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010   -1.8554   -0.8467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1291   -0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.3114    1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    1.2693    1.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    0.0317    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    0.7497    1.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7558    0.5037    1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763   -0.4503    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470   -0.6281    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508    0.1503    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9377   -0.0186    0.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366    1.1075    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    1.2955    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231   -0.0210    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.9786    1.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -0.6791    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -0.2919    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.4622   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    1.6953   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.3797    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    2.4006   -1.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496   -3.8071   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -4.2703   -1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -3.0415   -2.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -2.8784   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -2.5959   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.7223    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    1.5332    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976   -1.1069   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0052   -1.3954   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3590    0.5331   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7521    1.7419    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078    2.0698    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190    1.6309    2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.1970    0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535    0.3002    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -0.0786   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5679    1.7686    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.4786    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4633    3.3736    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468    2.1352   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    3.4857   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5585    2.0246   -1.8673 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  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  3  1  0
 18 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   26                                                            
CONECT    4   10   13                                                       
CONECT    5    8   14                                                       
CONECT    6    9   14                                                       
CONECT    7   11   14                                                       
CONECT    8    5   15                                                       
CONECT    9    6   15                                                       
CONECT   10    4   16                                                       
CONECT   11    7   17                                                       
CONECT   12   18   19                                                       
CONECT   13    1    2    4                                                  
CONECT   14    5    6    7                                                  
CONECT   15    8    9   22                                                  
CONECT   16   10   19   21                                                  
CONECT   17   11   20   23                                                  
CONECT   18   12   20   24                                                  
CONECT   19   12   16   26                                                  
CONECT   20   17   18   21                                                  
CONECT   21   16   20   25                                                  
CONECT   22   15                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0035002
HETATM    1  C1  UNL     1      -3.187  -3.439  -2.136  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.375  -2.382  -1.225  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.306  -1.700  -0.655  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.045  -2.071  -0.995  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.046  -1.411  -0.445  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.301  -1.855  -0.847  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.129  -0.371   0.453  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.987   0.311   1.027  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.758   1.269   1.854  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.400   0.032   0.770  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.350   0.750   1.380  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.756   0.504   1.152  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.276  -0.450   0.312  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.647  -0.628   0.146  1.00  0.00           C  
HETATM   15  C12 UNL     1       7.551   0.150   0.822  1.00  0.00           C  
HETATM   16  O4  UNL     1       8.938  -0.019   0.664  1.00  0.00           O  
HETATM   17  C13 UNL     1       7.037   1.108   1.665  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.696   1.295   1.839  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.423  -0.021   0.775  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.721   0.979   1.640  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.529  -0.679   0.227  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.929  -0.292   0.589  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.485   0.462  -0.565  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.971   1.695  -0.488  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.968   2.380   0.822  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.512   2.401  -1.677  1.00  0.00           C  
HETATM   27  H1  UNL     1      -4.150  -3.807  -2.499  1.00  0.00           H  
HETATM   28  H2  UNL     1      -2.594  -4.270  -1.706  1.00  0.00           H  
HETATM   29  H3  UNL     1      -2.615  -3.041  -2.995  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.825  -2.878  -1.693  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.440  -2.596  -1.487  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.772  -0.722   0.115  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.046   1.533   2.061  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.598  -1.107  -0.259  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.005  -1.395  -0.529  1.00  0.00           H  
HETATM   36  H10 UNL     1       9.359   0.533  -0.072  1.00  0.00           H  
HETATM   37  H11 UNL     1       7.752   1.742   2.216  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.308   2.070   2.520  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.319   1.631   2.194  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.527  -1.197   0.732  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.953   0.300   1.522  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.471  -0.079  -1.522  1.00  0.00           H  
HETATM   43  H17 UNL     1      -5.568   1.769   1.552  1.00  0.00           H  
HETATM   44  H18 UNL     1      -3.956   2.479   1.232  1.00  0.00           H  
HETATM   45  H19 UNL     1      -5.463   3.374   0.693  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.947   2.135  -2.603  1.00  0.00           H  
HETATM   47  H21 UNL     1      -5.496   3.486  -1.481  1.00  0.00           H  
HETATM   48  H22 UNL     1      -6.558   2.025  -1.867  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   30
CONECT    5    6    7    7
CONECT    6   31
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   18
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   17
CONECT   16   36
CONECT   17   18   18   37
CONECT   18   38
CONECT   19   20   21   21
CONECT   20   39
CONECT   21   22
CONECT   22   23   40   41
CONECT   23   24   24   42
CONECT   24   25   26
CONECT   25   43   44   45
CONECT   26   46   47   48
END

HMDB0035002
     RDKit          3D
Xanthogalenol
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.1872   -3.4385   -2.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3753   -2.3816   -1.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065   -1.6995   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454   -2.0708   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463   -1.4112   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010   -1.8554   -0.8467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1291   -0.3713    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    0.3114    1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    1.2693    1.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    0.0317    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    0.7497    1.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7558    0.5037    1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763   -0.4503    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470   -0.6281    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508    0.1503    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9377   -0.0186    0.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366    1.1075    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    1.2955    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231   -0.0210    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.9786    1.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -0.6791    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -0.2919    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.4622   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9706    1.6953   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    2.3797    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    2.4006   -1.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496   -3.8071   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -4.2703   -1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -3.0415   -2.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -2.8784   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -2.5959   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.7223    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    1.5332    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976   -1.1069   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0052   -1.3954   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3590    0.5331   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7521    1.7419    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078    2.0698    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190    1.6309    2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.1970    0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535    0.3002    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707   -0.0786   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5679    1.7686    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.4786    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4633    3.3736    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468    2.1352   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    3.4857   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5585    2.0246   -1.8673 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  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  3  1  0
 18 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3' Prenyl-4' O-methylchalconaringenin	ChEBI
3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalcone	ChEBI
2',4,6'-Trihydroxy-4'-methoxy-3'-prenylchalcone	HMDB

Chemical Formula

C₂₁H₂₂O₅

Average Molecular Weight

354.3964

Monoisotopic Molecular Weight

354.146723814

IUPAC Name

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

Traditional Name

xanthogalenol

CAS Registry Number

265659-35-6

SMILES

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

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)4-10-16-19(26-3)12-18(24)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

ALGFNVZQNNGHPA-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

Chalcones and dihydrochalcones (LMPK12120307 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035002)
Cell membrane (HMDB: HMDB0035002)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035002)

Source

Exogenous

Exogenous (HMDB: HMDB0035002)

Food

Food (HMDB: HMDB0035002)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0035002)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035002)

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	0.11 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	0.0058 g/L	ALOGPS
logP	3.93	ALOGPS
logP	5.85	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.82	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	38.85 Å³	ChemAxon
Number of Rings	2	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]+	191.466	30932474
DeepCCS	[M-H]-	189.108	30932474
DeepCCS	[M-2H]-	222.597	30932474
DeepCCS	[M+Na]+	197.826	30932474
AllCCS	[M+H]+	187.6	32859911
AllCCS	[M+H-H2O]+	184.4	32859911
AllCCS	[M+NH4]+	190.6	32859911
AllCCS	[M+Na]+	191.5	32859911
AllCCS	[M-H]-	185.0	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	184.9	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.	9.41 minutes	32390414
Predicted by Siyang on May 30, 2022	16.9676 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3184.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	387.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	828.9 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	825.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1612.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	688.8 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	1533.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	550.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	560.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	302.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	227.6 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	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthogalenol	COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1	4940.4	Standard polar	33892256
Xanthogalenol	COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1	3090.5	Standard non polar	33892256
Xanthogalenol	COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1	3340.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthogalenol,1TMS,isomer #1	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C	3185.6	Semi standard non polar	33892256
Xanthogalenol,1TMS,isomer #2	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=C1CC=C(C)C	3169.9	Semi standard non polar	33892256
Xanthogalenol,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C	3181.3	Semi standard non polar	33892256
Xanthogalenol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C	3144.5	Semi standard non polar	33892256
Xanthogalenol,2TMS,isomer #2	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C	3143.7	Semi standard non polar	33892256
Xanthogalenol,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=C1CC=C(C)C	3145.2	Semi standard non polar	33892256
Xanthogalenol,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C	3176.1	Semi standard non polar	33892256
Xanthogalenol,1TBDMS,isomer #1	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3457.1	Semi standard non polar	33892256
Xanthogalenol,1TBDMS,isomer #2	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=C1CC=C(C)C	3434.7	Semi standard non polar	33892256
Xanthogalenol,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C	3432.9	Semi standard non polar	33892256
Xanthogalenol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3663.7	Semi standard non polar	33892256
Xanthogalenol,2TBDMS,isomer #2	COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3677.5	Semi standard non polar	33892256
Xanthogalenol,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=C1CC=C(C)C	3677.9	Semi standard non polar	33892256
Xanthogalenol,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3901.2	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 - Xanthogalenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-3459000000-8086a86ef04627fc559a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthogalenol GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-1001290000-27ebccdf6673fc73908e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthogalenol 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 - Xanthogalenol 10V, Positive-QTOF	splash10-0a4i-0129000000-836af65cb4ae74175c88	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 20V, Positive-QTOF	splash10-05mt-3696000000-ae1e87c202e1b83d3717	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 40V, Positive-QTOF	splash10-016r-4910000000-093de7a4a5c7916eede6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 10V, Negative-QTOF	splash10-0udi-0129000000-a92805839c571d453a6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 20V, Negative-QTOF	splash10-0pbd-0955000000-c208ad3f8d4edb90545f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 40V, Negative-QTOF	splash10-0avm-1930000000-a40d21950ef93ac5ba5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 10V, Negative-QTOF	splash10-0udi-0009000000-cf0d5b7646fbfcac4d81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 20V, Negative-QTOF	splash10-0udi-0259000000-d59a2bac22530a37d7a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 40V, Negative-QTOF	splash10-014l-1920000000-b28a071e0b0ec5ee3247	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 10V, Positive-QTOF	splash10-0a4j-0429000000-a2c14b4be6145244b068	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 20V, Positive-QTOF	splash10-004i-0931000000-9a041dc31a2b43b191af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthogalenol 40V, Positive-QTOF	splash10-00or-2911000000-a04ec936ed7cafb4f3cc	2021-09-22	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

FDB013606

KNApSAcK ID

C00014475

Chemspider ID

24692988

KEGG Compound ID

Not Available

BioCyc ID

CPD-7121

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14309735

PDB ID

Not Available

ChEBI ID

136826

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846881

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 Xanthogalenol (HMDB0035002)

MOL for HMDB0035002 (Xanthogalenol)

3D MOL for HMDB0035002 (Xanthogalenol)

3D SDF for HMDB0035002 (Xanthogalenol)

3D-SDF for HMDB0035002 (Xanthogalenol)

PDB for HMDB0035002 (Xanthogalenol)

3D PDB for HMDB0035002 (Xanthogalenol)

SMILES for HMDB0035002 (Xanthogalenol)

INCHI for HMDB0035002 (Xanthogalenol)

Structure for HMDB0035002 (Xanthogalenol)

3D Structure for HMDB0035002 (Xanthogalenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra