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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:56:32 UTC

Update Date

2022-03-07 02:54:19 UTC

HMDB ID

HMDB0035003

Secondary Accession Numbers

HMDB35003

Metabolite Identification

Common Name

Xanthohumol D

Description

Xanthohumol D 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 D is considered to be a flavonoid. Xanthohumol D has been detected, but not quantified in, alcoholic beverages. This could make xanthohumol D a potential biomarker for the consumption of these foods. Xanthohumol D 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 Xanthohumol D.

Structure

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


  Mrv0541 05061308112D          

 27 28  0  0  0  0            999 V2000
   -5.0013   -2.8875    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
   -0.7145    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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    0.8250    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
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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
   -4.2868   -1.6500    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
   -3.5724    1.2375    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
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    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
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 12  1  2  0  0  0  0
 12  2  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 20 16  1  0  0  0  0
 20 19  2  0  0  0  0
 21 15  2  0  0  0  0
 21 20  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 21  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
M  END

HMDB0035003
     RDKit          3D
Xanthohumol D
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.6849    1.4037    0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.3791    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9806    0.6613    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0915   -1.0504    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738   -1.5854    2.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.1655    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395   -0.5495   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   -0.1743   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -0.3763   -1.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.4186   -2.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5977    0.6392   -2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    1.2514   -3.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587    1.5975   -4.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    0.2742   -1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5430    0.5307   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    1.1298   -2.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.3703   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649   -0.1222    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -0.1633    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269   -0.7312    2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193   -0.8277    3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7632   -0.3412    2.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9804   -0.4256    3.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631    0.2284    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399    0.3204    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -0.3191   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.7241    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.3265    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0819    2.4181    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4539    0.3676    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3965   -0.0049    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1617    1.7235    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6533   -1.6533    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -2.5591    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2743   -2.2206    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -0.6165    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860   -0.1033   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.7070   -3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    2.2720   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    2.0409   -5.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425    0.6455   -5.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.7646   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.5366    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5533   -1.1352    2.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900   -1.2777    4.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5813   -1.2349    3.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.6169    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    0.7796   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -1.1685    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 14 26  2  0
 26 27  1  0
 26  7  1  0
 25 19  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  1  0
M  END


  Mrv0541 05061308112D          

 27 28  0  0  0  0            999 V2000
   -5.0013   -2.8875    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
   -0.7145    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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    0.8250    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
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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
   -4.2868   -1.6500    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
   -3.5724    1.2375    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
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    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
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 12  1  2  0  0  0  0
 12  2  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 20 16  1  0  0  0  0
 20 19  2  0  0  0  0
 21 15  2  0  0  0  0
 21 20  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 21  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035003

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+

> <INCHI_KEY>
IIWLGOCXDBSFCM-RMKNXTFCSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.3958

> <EXACT_MASS>
370.141638436

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
39.548405468457425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
4.027647680999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.853540034790267

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.972265735073855

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0490866005400292

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
103.96869999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthohumol D

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035003
     RDKit          3D
Xanthohumol D
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.6849    1.4037    0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.3791    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9806    0.6613    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0915   -1.0504    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738   -1.5854    2.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.1655    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395   -0.5495   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   -0.1743   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -0.3763   -1.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.4186   -2.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5977    0.6392   -2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    1.2514   -3.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587    1.5975   -4.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    0.2742   -1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5430    0.5307   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    1.1298   -2.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.3703   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649   -0.1222    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -0.1633    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269   -0.7312    2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193   -0.8277    3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7632   -0.3412    2.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9804   -0.4256    3.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631    0.2284    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399    0.3204    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -0.3191   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.7241    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.3265    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0819    2.4181    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4539    0.3676    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3965   -0.0049    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1617    1.7235    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6533   -1.6533    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -2.5591    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2743   -2.2206    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -0.6165    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860   -0.1033   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.7070   -3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    2.2720   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    2.0409   -5.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425    0.6455   -5.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.7646   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.5366    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5533   -1.1352    2.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900   -1.2777    4.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5813   -1.2349    3.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.6169    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    0.7796   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -1.1685    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 14 26  2  0
 26 27  1  0
 26  7  1  0
 25 19  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  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      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   27                                                            
CONECT    4    7   13                                                       
CONECT    5    8   13                                                       
CONECT    6    9   13                                                       
CONECT    7    4   14                                                       
CONECT    8    5   14                                                       
CONECT    9    6   16                                                       
CONECT   10   15   17                                                       
CONECT   11   18   19                                                       
CONECT   12    1    2   17                                                  
CONECT   13    4    5    6                                                  
CONECT   14    7    8   22                                                  
CONECT   15   10   18   21                                                  
CONECT   16    9   20   23                                                  
CONECT   17   10   12   24                                                  
CONECT   18   11   15   25                                                  
CONECT   19   11   20   27                                                  
CONECT   20   16   19   21                                                  
CONECT   21   15   20   26                                                  
CONECT   22   14                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   21                                                            
CONECT   27    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0035003
HETATM    1  C1  UNL     1      -3.685   1.404   0.967  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.509   0.379   0.879  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.981   0.661   0.865  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.092  -1.050   0.808  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.474  -1.585   2.077  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.602  -1.166   0.742  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.940  -0.550  -0.406  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.608  -0.174  -1.531  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.996  -0.376  -1.675  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.946   0.419  -2.578  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.598   0.639  -2.501  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.021   1.251  -3.606  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.759   1.597  -4.709  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.160   0.274  -1.365  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.543   0.531  -1.377  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.934   1.130  -2.528  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.698   0.370  -0.572  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.965  -0.122   0.599  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.309  -0.163   1.223  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.427  -0.731   2.474  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.619  -0.828   3.158  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.763  -0.341   2.587  1.00  0.00           C  
HETATM   23  O5  UNL     1       7.980  -0.426   3.255  1.00  0.00           O  
HETATM   24  C19 UNL     1       6.663   0.228   1.338  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.440   0.320   0.652  1.00  0.00           C  
HETATM   26  C21 UNL     1      -0.572  -0.319  -0.347  1.00  0.00           C  
HETATM   27  O6  UNL     1       0.046  -0.724   0.807  1.00  0.00           O  
HETATM   28  H1  UNL     1      -2.594   1.327   0.987  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.082   2.418   1.027  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.454   0.368   1.811  1.00  0.00           H  
HETATM   31  H4  UNL     1      -6.397  -0.005   0.069  1.00  0.00           H  
HETATM   32  H5  UNL     1      -6.162   1.724   0.666  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.653  -1.653   0.090  1.00  0.00           H  
HETATM   34  H7  UNL     1      -4.292  -2.559   2.062  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.274  -2.221   0.819  1.00  0.00           H  
HETATM   36  H9  UNL     1      -2.208  -0.617   1.646  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.486  -0.103  -2.496  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.516   0.707  -3.465  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.595   2.272  -4.384  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.155   2.041  -5.505  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.242   0.645  -5.075  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.685   0.765  -1.032  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.181  -0.537   1.177  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.553  -1.135   2.982  1.00  0.00           H  
HETATM   45  H18 UNL     1       5.690  -1.278   4.142  1.00  0.00           H  
HETATM   46  H19 UNL     1       8.581  -1.235   3.138  1.00  0.00           H  
HETATM   47  H20 UNL     1       7.569   0.617   0.879  1.00  0.00           H  
HETATM   48  H21 UNL     1       5.444   0.780  -0.319  1.00  0.00           H  
HETATM   49  H22 UNL     1      -0.402  -1.168   1.545  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3    4
CONECT    3   30   31   32
CONECT    4    5    6   33
CONECT    5   34
CONECT    6    7   35   36
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   37
CONECT   10   11   11   38
CONECT   11   12   14
CONECT   12   13
CONECT   13   39   40   41
CONECT   14   15   26   26
CONECT   15   16   16   17
CONECT   17   18   18   42
CONECT   18   19   43
CONECT   19   20   20   25
CONECT   20   21   44
CONECT   21   22   22   45
CONECT   22   23   24
CONECT   23   46
CONECT   24   25   25   47
CONECT   25   48
CONECT   26   27
CONECT   27   49
END

HMDB0035003
     RDKit          3D
Xanthohumol D
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.6849    1.4037    0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.3791    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9806    0.6613    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0915   -1.0504    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738   -1.5854    2.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018   -1.1655    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395   -0.5495   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   -0.1743   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -0.3763   -1.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.4186   -2.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5977    0.6392   -2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    1.2514   -3.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587    1.5975   -4.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    0.2742   -1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5430    0.5307   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    1.1298   -2.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.3703   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649   -0.1222    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -0.1633    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269   -0.7312    2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193   -0.8277    3.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7632   -0.3412    2.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9804   -0.4256    3.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6631    0.2284    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399    0.3204    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722   -0.3191   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.7241    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.3265    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0819    2.4181    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4539    0.3676    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3965   -0.0049    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1617    1.7235    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6533   -1.6533    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -2.5591    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2743   -2.2206    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077   -0.6165    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860   -0.1033   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.7070   -3.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    2.2720   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    2.0409   -5.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425    0.6455   -5.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.7646   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.5366    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5533   -1.1352    2.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900   -1.2777    4.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5813   -1.2349    3.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.6169    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436    0.7796   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -1.1685    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 14 26  2  0
 26 27  1  0
 26  7  1  0
 25 19  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3'-(2-Hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalcone	ChEBI
rac-(2E)-1-{2,4-dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one	ChEBI

Chemical Formula

C₂₁H₂₂O₆

Average Molecular Weight

370.3958

Monoisotopic Molecular Weight

370.141638436

IUPAC Name

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

Traditional Name

xanthohumol D

CAS Registry Number

274675-25-1

SMILES

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

InChI Identifier

InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+

InChI Key

IIWLGOCXDBSFCM-RMKNXTFCSA-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
Benzoyl
Phenol ether
Resorcinol
Styrene
Aryl ketone
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Acryloyl-group
Alpha,beta-unsaturated ketone
Vinylogous acid
Enone
Secondary alcohol
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:66335 )
secondary alcohol (CHEBI:66335 )
polyphenol (CHEBI:66335 )
chalcones (CHEBI:66335 )
Chalcones and dihydrochalcones (LMPK12120295 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035003)

Cellular substructure

Membrane (HMDB: HMDB0035003)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035003)

Source

Exogenous

Food

Food (HMDB: HMDB0035003)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0035003)

Not Available

Nutrient (HMDB: HMDB0035003)

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	23.41 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	0.046 g/L	ALOGPS
logP	2.85	ALOGPS
logP	4.03	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.97 m³·mol⁻¹	ChemAxon
Polarizability	39.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	193.503	30932474
DeepCCS	[M-H]-	191.117	30932474
DeepCCS	[M-2H]-	224.278	30932474
DeepCCS	[M+Na]+	199.568	30932474
AllCCS	[M+H]+	191.7	32859911
AllCCS	[M+H-H2O]+	188.6	32859911
AllCCS	[M+NH4]+	194.5	32859911
AllCCS	[M+Na]+	195.3	32859911
AllCCS	[M-H]-	189.4	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	190.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol D	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC(O)C(C)=C)C(O)=C1	5317.1	Standard polar	33892256
Xanthohumol D	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC(O)C(C)=C)C(O)=C1	3018.3	Standard non polar	33892256
Xanthohumol D	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC(O)C(C)=C)C(O)=C1	3612.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthohumol D,1TMS,isomer #1	C=C(C)C(O)CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3351.9	Semi standard non polar	33892256
Xanthohumol D,1TMS,isomer #2	C=C(C)C(O)CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3341.7	Semi standard non polar	33892256
Xanthohumol D,1TMS,isomer #3	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O)O[Si](C)(C)C	3342.4	Semi standard non polar	33892256
Xanthohumol D,1TMS,isomer #4	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3304.6	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #1	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O)O[Si](C)(C)C	3268.4	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #2	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O	3250.0	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #3	C=C(C)C(O)CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3278.2	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #4	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C)O[Si](C)(C)C	3271.2	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #5	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C	3254.3	Semi standard non polar	33892256
Xanthohumol D,2TMS,isomer #6	C=C(C)C(CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O)O[Si](C)(C)C	3223.5	Semi standard non polar	33892256
Xanthohumol D,3TMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O)O[Si](C)(C)C	3251.2	Semi standard non polar	33892256
Xanthohumol D,3TMS,isomer #2	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C)O[Si](C)(C)C	3245.2	Semi standard non polar	33892256
Xanthohumol D,3TMS,isomer #3	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C	3267.6	Semi standard non polar	33892256
Xanthohumol D,3TMS,isomer #4	C=C(C)C(CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C)O[Si](C)(C)C	3223.4	Semi standard non polar	33892256
Xanthohumol D,4TMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C)O[Si](C)(C)C	3292.0	Semi standard non polar	33892256
Xanthohumol D,1TBDMS,isomer #1	C=C(C)C(O)CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3619.1	Semi standard non polar	33892256
Xanthohumol D,1TBDMS,isomer #2	C=C(C)C(O)CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3617.7	Semi standard non polar	33892256
Xanthohumol D,1TBDMS,isomer #3	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O)O[Si](C)(C)C(C)(C)C	3595.6	Semi standard non polar	33892256
Xanthohumol D,1TBDMS,isomer #4	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O	3553.1	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #1	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O)O[Si](C)(C)C(C)(C)C	3796.0	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #2	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O	3782.0	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #3	C=C(C)C(O)CC1=C(O)C=C(OC)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	3816.3	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #4	C=C(C)C(CC1=C(O)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3812.7	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #5	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C	3772.2	Semi standard non polar	33892256
Xanthohumol D,2TBDMS,isomer #6	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O)O[Si](C)(C)C(C)(C)C	3739.3	Semi standard non polar	33892256
Xanthohumol D,3TBDMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O)O[Si](C)(C)C(C)(C)C	4007.6	Semi standard non polar	33892256
Xanthohumol D,3TBDMS,isomer #2	C=C(C)C(CC1=C(O)C=C(OC)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)O[Si](C)(C)C(C)(C)C	3985.0	Semi standard non polar	33892256
Xanthohumol D,3TBDMS,isomer #3	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)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	3989.3	Semi standard non polar	33892256
Xanthohumol D,3TBDMS,isomer #4	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3932.5	Semi standard non polar	33892256
Xanthohumol D,4TBDMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=C(OC)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)O[Si](C)(C)C(C)(C)C	4182.9	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 D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdp-9257000000-e93616bcdfc00d5f0eff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol D GC-MS (4 TMS) - 70eV, Positive	splash10-0006-4100159000-a73946662fee744891e0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthohumol D 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 D 10V, Positive-QTOF	splash10-0fk9-0129000000-f79c99b20767293c1063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 20V, Positive-QTOF	splash10-00ds-9343000000-2a20e5aedac4bddb9324	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 40V, Positive-QTOF	splash10-0l7i-6940000000-25b60ac9ed7eff1613a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 10V, Negative-QTOF	splash10-014i-0039000000-692ffe7dfab4150019f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 20V, Negative-QTOF	splash10-0671-1493000000-424d244d7b00e13bc886	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 40V, Negative-QTOF	splash10-067i-9520000000-677eddaac31484f3246b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 10V, Positive-QTOF	splash10-0fk9-0019000000-11a1964c498d91ff1132	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 20V, Positive-QTOF	splash10-0f6t-1963000000-6e9da9f0627794e55667	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 40V, Positive-QTOF	splash10-001i-2910000000-a64df3dda5e77ae4f800	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 10V, Negative-QTOF	splash10-014i-0009000000-53e6b228c1fcbc5c164f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 20V, Negative-QTOF	splash10-014i-1749000000-2a4c83fe1b493b0ee475	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthohumol D 40V, Negative-QTOF	splash10-014i-2933000000-c39e9b1fa1c7eef6c3d5	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

FDB013607

KNApSAcK ID

C00014472

Chemspider ID

8492534

KEGG Compound ID

Not Available

BioCyc ID

CPD-7129

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10317069

PDB ID

Not Available

ChEBI ID

66335

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846891

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 D (HMDB0035003)

MOL for HMDB0035003 (Xanthohumol D)

3D MOL for HMDB0035003 (Xanthohumol D)

3D SDF for HMDB0035003 (Xanthohumol D)

3D-SDF for HMDB0035003 (Xanthohumol D)

PDB for HMDB0035003 (Xanthohumol D)

3D PDB for HMDB0035003 (Xanthohumol D)

SMILES for HMDB0035003 (Xanthohumol D)

INCHI for HMDB0035003 (Xanthohumol D)

Structure for HMDB0035003 (Xanthohumol D)

3D Structure for HMDB0035003 (Xanthohumol D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra