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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:32:59 UTC

Update Date

2021-09-23 03:33:00 UTC

HMDB ID

HMDB0301908

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xanthoangelol D

Description

Xanthoangelol d 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 d is considered to be a flavonoid lipid molecule. Xanthoangelol d is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Xanthoangelol d can be found in angelica, which makes xanthoangelol d a potential biomarker for the consumption of this food product.

Structure

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

 
  Mrv0541 02241221082D          

 26 27  0  0  0  0            999 V2000
   -1.1277    0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7301   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -1.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -1.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
  7 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 19 26  1  0  0  0  0
M  END

HMDB0301908
     RDKit          3D
Xanthoangelol D
 48 49  0  0  0  0  0  0  0  0999 V2000
   -6.6681    0.7630   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639    1.3680   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    2.6152    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.8257   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3330   -0.2725   -1.5304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    0.5143    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608   -0.0301    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -1.3440    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423   -2.1338   -0.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685   -3.4815   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809   -1.8986   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.1224    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712    0.1874    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.0271    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    2.2883    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    0.7989    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -0.2044    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0445   -0.1605    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483   -1.3119   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1288   -1.3330   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8711   -0.1995   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667   -0.2210   -0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1842    0.9384    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769    0.9527    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    0.7503    0.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827    2.0243    0.9168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5842   -0.1439   -1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6628    1.1363   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    2.3381    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583    3.4145   -0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8283    2.9929    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    1.6373   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -0.0383   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239   -0.2854    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    1.3669    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -3.9134   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179   -3.5879   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986   -3.9662    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609   -2.9321   -0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.6244   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    1.7257    0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -1.1409   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1808   -2.2102   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6655   -2.2336   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933   -0.4596    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7519    1.8319    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3207    1.8793    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    2.8726    1.1366 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
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 13 25  2  0
 25 26  1  0
 25  7  1  0
 24 18  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
M  END

 
  Mrv0541 02241221082D          

 26 27  0  0  0  0            999 V2000
   -1.1277    0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7301   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735   -0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -0.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -1.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -1.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712    0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
  7 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 19 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301908

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC(O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)19(24)12-17-20(26-3)11-9-16(21(17)25)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,19,22,24-25H,1,12H2,2-3H3/b10-6+

> <INCHI_KEY>
YSOKENZJQWPLRA-UXBLZVDNSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.902982384264064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
4.331213002666666

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.112576895823786

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.246180823362693

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0593517556375085

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
101.9878

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthoangelol D

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301908
     RDKit          3D
Xanthoangelol D
 48 49  0  0  0  0  0  0  0  0999 V2000
   -6.6681    0.7630   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639    1.3680   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    2.6152    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.8257   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3330   -0.2725   -1.5304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    0.5143    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608   -0.0301    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -1.3440    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423   -2.1338   -0.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685   -3.4815   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809   -1.8986   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.1224    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712    0.1874    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.0271    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    2.2883    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    0.7989    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -0.2044    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0445   -0.1605    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483   -1.3119   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1288   -1.3330   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8711   -0.1995   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667   -0.2210   -0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1842    0.9384    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769    0.9527    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    0.7503    0.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827    2.0243    0.9168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5842   -0.1439   -1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6628    1.1363   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    2.3381    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583    3.4145   -0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8283    2.9929    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    1.6373   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -0.0383   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239   -0.2854    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    1.3669    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -3.9134   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179   -3.5879   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986   -3.9662    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609   -2.9321   -0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.6244   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    1.7257    0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -1.1409   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1808   -2.2102   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6655   -2.2336   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933   -0.4596    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7519    1.8319    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3207    1.8793    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    2.8726    1.1366 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
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 13 25  2  0
 25 26  1  0
 25  7  1  0
 24 18  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.105   1.676   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.439   0.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.439  -0.634   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.105  -1.404   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.771  -0.634   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.771   0.906   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.562  -1.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.896  -0.634   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.230  -1.404   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.563  -0.634   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.897   1.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.563   0.906   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.897  -1.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.231  -0.634   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.231   0.906   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.562  -2.944   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.564   1.676   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.105  -2.944   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.773   1.676   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.773  -1.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.773  -2.944   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.106  -3.714   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.106  -5.254   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.440  -2.944   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.439  -3.714   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.106   0.906   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   17                                                  
CONECT   16    7                                                            
CONECT   17   15                                                            
CONECT   18    4                                                            
CONECT   19    2   26                                                       
CONECT   20    3   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21                                                            
CONECT   26   19                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0301908
HETATM    1  C1  UNL     1      -6.668   0.763  -0.863  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.564   1.368  -0.424  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.759   2.615   0.375  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.209   0.826  -0.719  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.333  -0.273  -1.530  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.505   0.514   0.577  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.161  -0.030   0.394  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.999  -1.344   0.033  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.142  -2.134  -0.139  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.969  -3.481  -0.511  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.781  -1.899  -0.161  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.366  -1.122   0.008  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.271   0.187   0.366  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.426   1.027   0.549  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.162   2.288   0.897  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.801   0.799   0.437  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.568  -0.204   0.141  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.044  -0.160   0.097  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.748  -1.312  -0.242  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.129  -1.333  -0.298  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.871  -0.199  -0.017  1.00  0.00           C  
HETATM   22  O4  UNL     1       9.267  -0.221  -0.074  1.00  0.00           O  
HETATM   23  C19 UNL     1       7.184   0.938   0.318  1.00  0.00           C  
HETATM   24  C20 UNL     1       5.777   0.953   0.373  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.017   0.750   0.565  1.00  0.00           C  
HETATM   26  O5  UNL     1      -1.183   2.024   0.917  1.00  0.00           O  
HETATM   27  H1  UNL     1      -6.584  -0.144  -1.447  1.00  0.00           H  
HETATM   28  H2  UNL     1      -7.663   1.136  -0.665  1.00  0.00           H  
HETATM   29  H3  UNL     1      -6.506   2.338   1.176  1.00  0.00           H  
HETATM   30  H4  UNL     1      -6.258   3.415  -0.232  1.00  0.00           H  
HETATM   31  H5  UNL     1      -4.828   2.993   0.809  1.00  0.00           H  
HETATM   32  H6  UNL     1      -3.607   1.637  -1.204  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.502  -0.038  -2.466  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.124  -0.285   1.077  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.490   1.367   1.254  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.975  -3.913  -0.655  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.418  -3.588  -1.464  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.399  -3.966   0.313  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.661  -2.932  -0.446  1.00  0.00           H  
HETATM   40  H14 UNL     1       1.304  -1.624  -0.162  1.00  0.00           H  
HETATM   41  H15 UNL     1       3.441   1.726   0.658  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.126  -1.141  -0.091  1.00  0.00           H  
HETATM   43  H17 UNL     1       5.181  -2.210  -0.465  1.00  0.00           H  
HETATM   44  H18 UNL     1       7.665  -2.234  -0.563  1.00  0.00           H  
HETATM   45  H19 UNL     1       9.793  -0.460   0.757  1.00  0.00           H  
HETATM   46  H20 UNL     1       7.752   1.832   0.540  1.00  0.00           H  
HETATM   47  H21 UNL     1       5.321   1.879   0.642  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.895   2.873   1.137  1.00  0.00           H  
CONECT    1    2    2   27   28
CONECT    2    3    4
CONECT    3   29   30   31
CONECT    4    5    6   32
CONECT    5   33
CONECT    6    7   34   35
CONECT    7    8    8   25
CONECT    8    9   11
CONECT    9   10
CONECT   10   36   37   38
CONECT   11   12   12   39
CONECT   12   13   40
CONECT   13   14   25   25
CONECT   14   15   15   16
CONECT   16   17   17   41
CONECT   17   18   42
CONECT   18   19   19   24
CONECT   19   20   43
CONECT   20   21   21   44
CONECT   21   22   23
CONECT   22   45
CONECT   23   24   24   46
CONECT   24   47
CONECT   25   26
CONECT   26   48
END

HMDB0301908
     RDKit          3D
Xanthoangelol D
 48 49  0  0  0  0  0  0  0  0999 V2000
   -6.6681    0.7630   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639    1.3680   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    2.6152    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.8257   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3330   -0.2725   -1.5304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    0.5143    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608   -0.0301    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -1.3440    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423   -2.1338   -0.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685   -3.4815   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809   -1.8986   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.1224    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712    0.1874    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.0271    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    2.2883    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    0.7989    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -0.2044    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0445   -0.1605    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483   -1.3119   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1288   -1.3330   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8711   -0.1995   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667   -0.2210   -0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1842    0.9384    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769    0.9527    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    0.7503    0.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827    2.0243    0.9168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5842   -0.1439   -1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6628    1.1363   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    2.3381    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583    3.4145   -0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8283    2.9929    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    1.6373   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -0.0383   -2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239   -0.2854    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    1.3669    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -3.9134   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179   -3.5879   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986   -3.9662    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609   -2.9321   -0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.6244   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    1.7257    0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -1.1409   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1808   -2.2102   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6655   -2.2336   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933   -0.4596    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7519    1.8319    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3207    1.8793    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    2.8726    1.1366 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
  9 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 13 25  2  0
 25 26  1  0
 25  7  1  0
 24 18  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₅

Average Molecular Weight

354.3964

Monoisotopic Molecular Weight

354.146723814

IUPAC Name

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

Traditional Name

xanthoangelol D

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC(O)C(C)=C

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)19(24)12-17-20(26-3)11-9-16(21(17)25)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,19,22,24-25H,1,12H2,2-3H3/b10-6+

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120042 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301908)

Food

Herb and spice

Herb

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	3.29	ALOGPS
logP	4.33	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.1	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	7	ChemAxon
Refractivity	101.99 m³·mol⁻¹	ChemAxon
Polarizability	38.9 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]+	188.451	32859911
AllCCS	[M+H-H2O]+	185.255	32859911
AllCCS	[M+Na]+	192.259	32859911
AllCCS	[M+NH4]+	191.409	32859911
AllCCS	[M-H]-	186.707	32859911
AllCCS	[M+Na-2H]-	186.853	32859911
AllCCS	[M+HCOO]-	187.168	32859911
DeepCCS	[M+H]+	181.541	30932474
DeepCCS	[M-H]-	179.183	30932474
DeepCCS	[M-2H]-	213.262	30932474
DeepCCS	[M+Na]+	188.489	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 D 10V, Positive-QTOF	splash10-052r-0229000000-c66e31e35ec93aada068	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 20V, Positive-QTOF	splash10-00y1-9442000000-113eee9edd4dc64414c1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 40V, Positive-QTOF	splash10-00y4-4920000000-881382008a7d89309b8d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 10V, Negative-QTOF	splash10-0udi-0129000000-9fba5757ff8c25f74438	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 20V, Negative-QTOF	splash10-0gb9-2496000000-b65f59d066aa9349dd08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 40V, Negative-QTOF	splash10-014r-9320000000-37975275a1308ecd0c95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 10V, Positive-QTOF	splash10-052s-0069000000-43904f0dcf992d512fc2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 20V, Positive-QTOF	splash10-0532-3964000000-448392adfb3df14904cd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 40V, Positive-QTOF	splash10-014l-4910000000-fa64e25f73ffd42bd135	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 10V, Negative-QTOF	splash10-0udi-0009000000-a0154b2fc88de7189b1b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 20V, Negative-QTOF	splash10-0gb9-4569000000-167ccaeda58c57729141	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoangelol D 40V, Negative-QTOF	splash10-014i-5592000000-d9dadd8219d3a989fd69	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

FDB001599

KNApSAcK ID

Not Available

Chemspider ID

9477646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 D (HMDB0301908)

MOL for HMDB0301908 (Xanthoangelol D)

3D MOL for HMDB0301908 (Xanthoangelol D)

3D SDF for HMDB0301908 (Xanthoangelol D)

3D-SDF for HMDB0301908 (Xanthoangelol D)

PDB for HMDB0301908 (Xanthoangelol D)

3D PDB for HMDB0301908 (Xanthoangelol D)

SMILES for HMDB0301908 (Xanthoangelol D)

INCHI for HMDB0301908 (Xanthoangelol D)

Structure for HMDB0301908 (Xanthoangelol D)

3D Structure for HMDB0301908 (Xanthoangelol D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra