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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:33:26 UTC

Update Date

2021-09-23 03:33:26 UTC

HMDB ID

HMDB0301909

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xanthoangelol E

Description

Xanthoangelol e is a member of the class of compounds known as 3-prenylated chalcones. 3-prenylated chalcones are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, xanthoangelol e is considered to be a flavonoid lipid molecule. Xanthoangelol e is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Xanthoangelol e can be found in angelica, which makes xanthoangelol e a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241221222D          

 27 28  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    0.0000   -2.4750    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0301909
     RDKit          3D
Xanthoangelol E
 49 50  0  0  0  0  0  0  0  0999 V2000
   -5.7848    2.1447    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5226    1.0131   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063    0.4270   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3239   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    1.0671    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    0.4631    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315   -0.6213    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509   -1.1250    2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.2459    3.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032   -1.2079    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5036   -0.6850    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222    0.4053    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.9949   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418    2.0455   -1.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    0.6959   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932   -0.2154    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229   -0.2917   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.5465   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    0.4293   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8807   -0.5645   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2603   -0.6979   -0.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2061   -1.4477    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8553   -1.2962    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8581    0.9961    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.0660   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.2467   -1.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6225   -0.9825   -2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    2.6043    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7448    2.6307    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7518   -0.6308   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637    0.5361   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5406    0.9616   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7203   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    2.1021    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8529    1.1808    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3933   -1.9999    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735   -2.6314    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -3.0888    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.0696    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.1966    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4120   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -0.9286    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3257    1.3561   -1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6843    1.1155   -1.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7046   -0.0357   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843   -2.2094    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280   -1.9955    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496    2.7348   -1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -1.6116   -1.5826 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
  4 26  1  0
 26 27  1  0
 24  6  1  0
 23 17  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
  5 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 27 49  1  0
M  END


  Mrv0541 02241221222D          

 27 28  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    0.0000   -2.4750    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301909

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-13(2)20(27-25)12-17-19(26-3)11-9-16(21(17)24)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,20,22,24-25H,1,12H2,2-3H3/b10-6+

> <INCHI_KEY>
AJERVVHSERWGFL-UXBLZVDNSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.3958

> <EXACT_MASS>
370.141638436

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
39.61734062101022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
4.78054838

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.109092950195798

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.232714739697496

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237863078623392

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
103.33800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthoangelol E

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301909
     RDKit          3D
Xanthoangelol E
 49 50  0  0  0  0  0  0  0  0999 V2000
   -5.7848    2.1447    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5226    1.0131   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063    0.4270   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3239   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    1.0671    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    0.4631    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315   -0.6213    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509   -1.1250    2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.2459    3.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032   -1.2079    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5036   -0.6850    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222    0.4053    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.9949   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418    2.0455   -1.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    0.6959   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932   -0.2154    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229   -0.2917   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.5465   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    0.4293   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8807   -0.5645   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2603   -0.6979   -0.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2061   -1.4477    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8553   -1.2962    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8581    0.9961    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.0660   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.2467   -1.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6225   -0.9825   -2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    2.6043    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7448    2.6307    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7518   -0.6308   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637    0.5361   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5406    0.9616   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7203   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    2.1021    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8529    1.1808    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3933   -1.9999    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735   -2.6314    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -3.0888    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.0696    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.1966    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4120   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -0.9286    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3257    1.3561   -1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6843    1.1155   -1.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7046   -0.0357   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843   -2.2094    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280   -1.9955    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496    2.7348   -1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -1.6116   -1.5826 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
  4 26  1  0
 26 27  1  0
 24  6  1  0
 23 17  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
  5 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 27 49  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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24    7   25                                                       
CONECT   25   24                                                            
CONECT   26    4   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0301909
HETATM    1  C1  UNL     1      -5.785   2.145   0.135  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.523   1.013  -0.494  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.606   0.427  -1.366  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.209   0.324  -0.363  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.300   1.067   0.546  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.985   0.463   0.731  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.831  -0.621   1.535  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.951  -1.125   2.167  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.820  -2.246   3.004  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.603  -1.208   1.722  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.504  -0.685   1.077  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.422   0.405   0.252  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.547   0.995  -0.452  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.242   2.046  -1.199  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.928   0.696  -0.524  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.693  -0.215   0.016  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.123  -0.292  -0.241  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.812   0.546  -1.052  1.00  0.00           C  
HETATM   19  C17 UNL     1       7.181   0.429  -1.264  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.881  -0.564  -0.638  1.00  0.00           C  
HETATM   21  O3  UNL     1       9.260  -0.698  -0.839  1.00  0.00           O  
HETATM   22  C19 UNL     1       7.206  -1.448   0.205  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.855  -1.296   0.386  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.858   0.996   0.074  1.00  0.00           C  
HETATM   25  O4  UNL     1      -1.025   2.066  -0.716  1.00  0.00           O  
HETATM   26  O5  UNL     1      -3.695   0.247  -1.676  1.00  0.00           O  
HETATM   27  O6  UNL     1      -3.622  -0.983  -2.104  1.00  0.00           O  
HETATM   28  H1  UNL     1      -5.050   2.604   0.768  1.00  0.00           H  
HETATM   29  H2  UNL     1      -6.745   2.631   0.027  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.752  -0.631  -1.073  1.00  0.00           H  
HETATM   31  H4  UNL     1      -6.264   0.536  -2.415  1.00  0.00           H  
HETATM   32  H5  UNL     1      -7.541   0.962  -1.210  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.408  -0.720  -0.056  1.00  0.00           H  
HETATM   34  H7  UNL     1      -3.189   2.102   0.136  1.00  0.00           H  
HETATM   35  H8  UNL     1      -3.853   1.181   1.525  1.00  0.00           H  
HETATM   36  H9  UNL     1      -2.393  -2.000   4.001  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.874  -2.631   3.154  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.267  -3.089   2.584  1.00  0.00           H  
HETATM   39  H12 UNL     1      -0.530  -2.070   2.374  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.404  -1.197   1.277  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.501   1.412  -1.207  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.231  -0.929   0.674  1.00  0.00           H  
HETATM   43  H16 UNL     1       5.326   1.356  -1.581  1.00  0.00           H  
HETATM   44  H17 UNL     1       7.684   1.115  -1.916  1.00  0.00           H  
HETATM   45  H18 UNL     1       9.705  -0.036  -1.458  1.00  0.00           H  
HETATM   46  H19 UNL     1       7.784  -2.209   0.676  1.00  0.00           H  
HETATM   47  H20 UNL     1       5.328  -1.995   1.051  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.750   2.735  -1.292  1.00  0.00           H  
HETATM   49  H22 UNL     1      -4.187  -1.612  -1.583  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3    4
CONECT    3   30   31   32
CONECT    4    5   26   33
CONECT    5    6   34   35
CONECT    6    7    7   24
CONECT    7    8   10
CONECT    8    9
CONECT    9   36   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   24   24
CONECT   13   14   14   15
CONECT   15   16   16   41
CONECT   16   17   42
CONECT   17   18   18   23
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   22
CONECT   21   45
CONECT   22   23   23   46
CONECT   23   47
CONECT   24   25
CONECT   25   48
CONECT   26   27
CONECT   27   49
END

HMDB0301909
     RDKit          3D
Xanthoangelol E
 49 50  0  0  0  0  0  0  0  0999 V2000
   -5.7848    2.1447    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5226    1.0131   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063    0.4270   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3239   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    1.0671    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    0.4631    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315   -0.6213    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509   -1.1250    2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.2459    3.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032   -1.2079    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5036   -0.6850    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222    0.4053    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.9949   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418    2.0455   -1.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    0.6959   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932   -0.2154    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229   -0.2917   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.5465   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806    0.4293   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8807   -0.5645   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2603   -0.6979   -0.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2061   -1.4477    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8553   -1.2962    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8581    0.9961    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.0660   -0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954    0.2467   -1.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6225   -0.9825   -2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    2.6043    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7448    2.6307    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7518   -0.6308   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637    0.5361   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5406    0.9616   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7203   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    2.1021    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8529    1.1808    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3933   -1.9999    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735   -2.6314    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -3.0888    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.0696    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.1966    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4120   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -0.9286    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3257    1.3561   -1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6843    1.1155   -1.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7046   -0.0357   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7843   -2.2094    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280   -1.9955    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496    2.7348   -1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -1.6116   -1.5826 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  2  0
 24 25  1  0
  4 26  1  0
 26 27  1  0
 24  6  1  0
 23 17  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
  5 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 27 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₆

Average Molecular Weight

370.3958

Monoisotopic Molecular Weight

370.141638436

IUPAC Name

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

Traditional Name

xanthoangelol E

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H22O6/c1-13(2)20(27-25)12-17-19(26-3)11-9-16(21(17)24)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,20,22,24-25H,1,12H2,2-3H3/b10-6+

InChI Key

AJERVVHSERWGFL-UXBLZVDNSA-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
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Styrene
Aryl ketone
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Vinylogous acid
Hydroperoxide
Ketone
Peroxol
Ether
Alkyl hydroperoxide
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120043 )

Ontology

Not Available

Angelica (FooDB: FOOD00001)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.42	ALOGPS
logP	4.78	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.34 m³·mol⁻¹	ChemAxon
Polarizability	39.62 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
AllCCS	[M+H]+	191.516	32859911
AllCCS	[M+H-H2O]+	188.414	32859911
AllCCS	[M+Na]+	195.21	32859911
AllCCS	[M+NH4]+	194.386	32859911
AllCCS	[M-H]-	188.669	32859911
AllCCS	[M+Na-2H]-	188.768	32859911
AllCCS	[M+HCOO]-	189.035	32859911
DeepCCS	[M+H]+	187.79	30932474
DeepCCS	[M-H]-	185.432	30932474
DeepCCS	[M-2H]-	219.252	30932474
DeepCCS	[M+Na]+	194.466	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 10V, Positive-QTOF	splash10-00di-0239000000-b51fcfb90e54b36b77b1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 20V, Positive-QTOF	splash10-0udj-2944000000-475c119f4a6b1f1c03a0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 40V, Positive-QTOF	splash10-00kk-2910000000-742ad2eda946a0a1c8fc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 10V, Negative-QTOF	splash10-014i-0119000000-0380fe60ae42dd8c23e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 20V, Negative-QTOF	splash10-014i-1489000000-9ccd26fe56fdd359e84a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 40V, Negative-QTOF	splash10-0aps-9320000000-40d7a53720a2141f88b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 10V, Positive-QTOF	splash10-00dr-0089000000-e4bb33a68863a7229afd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 20V, Positive-QTOF	splash10-0002-7794000000-2fa0530fc3a49333104d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 40V, Positive-QTOF	splash10-014i-3911000000-f4814b9e41d8bbe98309	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 10V, Negative-QTOF	splash10-014i-0059000000-556a919151ebd5581d42	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 20V, Negative-QTOF	splash10-0159-1297000000-d9709b000e18f0f48d2a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol E 40V, Negative-QTOF	splash10-014i-7498000000-c600287ddb3580567ab9	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001600

KNApSAcK ID

C00007066

Chemspider ID

8197623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10022050

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Xanthoangelol E (HMDB0301909)

MOL for HMDB0301909 (Xanthoangelol E)

3D MOL for HMDB0301909 (Xanthoangelol E)

3D SDF for HMDB0301909 (Xanthoangelol E)

3D-SDF for HMDB0301909 (Xanthoangelol E)

PDB for HMDB0301909 (Xanthoangelol E)

3D PDB for HMDB0301909 (Xanthoangelol E)

SMILES for HMDB0301909 (Xanthoangelol E)

INCHI for HMDB0301909 (Xanthoangelol E)

Structure for HMDB0301909 (Xanthoangelol E)

3D Structure for HMDB0301909 (Xanthoangelol E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra