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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:21:08 UTC

Update Date

2022-03-07 02:54:29 UTC

HMDB ID

HMDB0035373

Secondary Accession Numbers

HMDB35373

Metabolite Identification

Common Name

Licoagroaurone

Description

Licoagroaurone belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Licoagroaurone has been detected, but not quantified in, several different foods, such as red tea, green tea, teas (Camellia sinensis), herbal tea, and black tea. This could make licoagroaurone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Licoagroaurone.

Structure

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

HMDB0035373
     RDKit          3D
Licoagroaurone
 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.9154    1.7637   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972    1.5019   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9992    2.5141   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    0.3730   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323    0.0909   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.1110    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -1.8576    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -1.4862   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -2.9837    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.3597    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.6293    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -1.5124    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -0.9665    0.5892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -1.7136    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -1.4574    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3011    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8434   -0.4801    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.5210   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8318    1.7412   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    2.7719   -1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872    1.9140   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    3.1256   -0.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.8829    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114   -2.8111    1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -3.6895    2.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    2.8478   -2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522    1.6821   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1789   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    3.3210    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    2.9018   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.9968    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -0.3604   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852    0.9970   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0017   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -1.9863    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -3.5606    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -4.2263    2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752   -2.1141    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3848   -1.4333    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.3663   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    2.6551   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968    3.8671   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839    1.0278    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 12  6  1  0
 23 16  1  0
 24 11  1  0
  1 26  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
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 17 39  1  0
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 22 42  1  0
 23 43  1  0
M  END

  Mrv0541 05061308252D          

 25 27  0  0  0  0            999 V2000
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  7  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 10  2  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 19  2  0  0  0  0
 25 18  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035373

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1O\C(=C/C1=CC(O)=C(O)C=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-11(2)3-5-13-15(21)8-6-14-19(24)18(25-20(13)14)10-12-4-7-16(22)17(23)9-12/h3-4,6-10,21-23H,5H2,1-2H3/b18-10-

> <INCHI_KEY>
GKIZWUHTCYQZHL-ZDLGFXPLSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.3539

> <EXACT_MASS>
338.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.01096899881672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.020145350666667

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.84749738679793

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.444905905076098

> <JCHEM_PKA_STRONGEST_BASIC>
-5.473294230871407

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
97.23179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035373
     RDKit          3D
Licoagroaurone
 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.9154    1.7637   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972    1.5019   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9992    2.5141   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    0.3730   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323    0.0909   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.1110    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -1.8576    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -1.4862   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -2.9837    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.3597    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.6293    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -1.5124    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -0.9665    0.5892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -1.7136    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -1.4574    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3011    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8434   -0.4801    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.5210   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8318    1.7412   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    2.7719   -1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872    1.9140   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    3.1256   -0.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.8829    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114   -2.8111    1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -3.6895    2.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    2.8478   -2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522    1.6821   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1789   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    3.3210    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    2.9018   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.9968    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -0.3604   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852    0.9970   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0017   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -1.9863    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -3.5606    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -4.2263    2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752   -2.1141    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3848   -1.4333    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.3663   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    2.6551   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968    3.8671   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839    1.0278    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 12  6  1  0
 23 16  1  0
 24 11  1  0
  1 26  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
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  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       2.530   9.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.713   5.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.483   6.844   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.023   6.844   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.793   5.510   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.793   8.177   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -7.333   5.510   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.744   0.132   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    5   11                                                       
CONECT    4    7   12                                                       
CONECT    5    3   13                                                       
CONECT    6    8   14                                                       
CONECT    7    4   16                                                       
CONECT    8    6   15                                                       
CONECT    9   12   17                                                       
CONECT   10   12   18                                                       
CONECT   11    1    2    3                                                  
CONECT   12    4    9   10                                                  
CONECT   13    5   15   20                                                  
CONECT   14    6   19   20                                                  
CONECT   15    8   13   21                                                  
CONECT   16    7   17   22                                                  
CONECT   17    9   16   23                                                  
CONECT   18   10   19   25                                                  
CONECT   19   14   18   24                                                  
CONECT   20   13   14   25                                                  
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   19                                                            
CONECT   25   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0035373
HETATM    1  C1  UNL     1      -4.915   1.764  -1.704  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.597   1.502  -1.073  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.999   2.514  -0.169  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.937   0.373  -1.302  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.632   0.091  -0.690  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.644  -1.111   0.174  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.757  -1.858   0.478  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.973  -1.486  -0.039  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.714  -2.984   1.294  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.494  -3.360   1.816  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.371  -2.629   1.525  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.416  -1.512   0.715  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.865  -0.967   0.589  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.782  -1.714   1.314  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.057  -1.457   1.395  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.600  -0.301   0.681  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.843  -0.480   0.119  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.457   0.521  -0.569  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.832   1.741  -0.712  1.00  0.00           C  
HETATM   20  O3  UNL     1       5.443   2.772  -1.409  1.00  0.00           O  
HETATM   21  C18 UNL     1       3.587   1.914  -0.146  1.00  0.00           C  
HETATM   22  O4  UNL     1       2.944   3.126  -0.277  1.00  0.00           O  
HETATM   23  C19 UNL     1       2.961   0.883   0.559  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.011  -2.811   1.941  1.00  0.00           C  
HETATM   25  O5  UNL     1       1.519  -3.689   2.675  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.898   2.848  -2.016  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.752   1.682  -0.991  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.070   1.179  -2.626  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.729   3.321   0.088  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.079   2.902  -0.622  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.807   1.997   0.811  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.375  -0.360  -1.969  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.285   0.997  -0.112  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.884  -0.002  -1.517  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.827  -1.986   0.144  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.596  -3.561   1.525  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.396  -4.226   2.457  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.675  -2.114   1.993  1.00  0.00           H  
HETATM   39  H14 UNL     1       5.385  -1.433   0.203  1.00  0.00           H  
HETATM   40  H15 UNL     1       6.449   0.366  -1.013  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.355   2.655  -1.826  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.397   3.867  -0.787  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.984   1.028   1.003  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   12   24
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   24
CONECT   15   16   38
CONECT   16   17   17   23
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   21
CONECT   20   41
CONECT   21   22   23   23
CONECT   22   42
CONECT   23   43
CONECT   24   25   25
END

HMDB0035373
     RDKit          3D
Licoagroaurone
 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.9154    1.7637   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972    1.5019   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9992    2.5141   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    0.3730   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6323    0.0909   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.1110    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -1.8576    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -1.4862   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -2.9837    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.3597    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.6293    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -1.5124    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -0.9665    0.5892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -1.7136    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -1.4574    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3011    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8434   -0.4801    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.5210   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8318    1.7412   -0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    2.7719   -1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872    1.9140   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    3.1256   -0.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.8829    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114   -2.8111    1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -3.6895    2.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979    2.8478   -2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522    1.6821   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1789   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    3.3210    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    2.9018   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.9968    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -0.3604   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852    0.9970   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0017   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -1.9863    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -3.5606    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -4.2263    2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752   -2.1141    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3848   -1.4333    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.3663   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    2.6551   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968    3.8671   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839    1.0278    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 12  6  1  0
 23 16  1  0
 24 11  1  0
  1 26  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
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₅

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

IUPAC Name

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-3-one

Traditional Name

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC2=C1O\C(=C/C1=CC(O)=C(O)C=C1)C2=O

InChI Identifier

InChI=1S/C20H18O5/c1-11(2)3-5-13-15(21)8-6-14-19(24)18(25-20(13)14)10-12-4-7-16(22)17(23)9-12/h3-4,6-10,21-23H,5H2,1-2H3/b18-10-

InChI Key

GKIZWUHTCYQZHL-ZDLGFXPLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzofuran
Coumaran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035373)
Cell membrane (HMDB: HMDB0035373)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035373)

Source

Exogenous

Exogenous (HMDB: HMDB0035373)

Food

Food (HMDB: HMDB0035373)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0035373)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035373)

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
Water Solubility	0.0092 g/L	ALOGPS
logP	4.05	ALOGPS
logP	4.02	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-5.5	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	3	ChemAxon
Refractivity	97.23 m³·mol⁻¹	ChemAxon
Polarizability	36.01 Å³	ChemAxon
Number of Rings	3	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]+	180.31	30932474
DeepCCS	[M-H]-	177.952	30932474
DeepCCS	[M-2H]-	211.962	30932474
DeepCCS	[M+Na]+	187.19	30932474
AllCCS	[M+H]+	182.7	32859911
AllCCS	[M+H-H2O]+	179.4	32859911
AllCCS	[M+NH4]+	185.8	32859911
AllCCS	[M+Na]+	186.7	32859911
AllCCS	[M-H]-	181.0	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licoagroaurone	CC(C)=CCC1=C(O)C=CC2=C1O\C(=C/C1=CC(O)=C(O)C=C1)C2=O	5065.1	Standard polar	33892256
Licoagroaurone	CC(C)=CCC1=C(O)C=CC2=C1O\C(=C/C1=CC(O)=C(O)C=C1)C2=O	3115.5	Standard non polar	33892256
Licoagroaurone	CC(C)=CCC1=C(O)C=CC2=C1O\C(=C/C1=CC(O)=C(O)C=C1)C2=O	3378.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licoagroaurone,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O)C(O)=C1)C2=O	3195.5	Semi standard non polar	33892256
Licoagroaurone,1TMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O)C(O[Si](C)(C)C)=C1)C2=O	3230.4	Semi standard non polar	33892256
Licoagroaurone,1TMS,isomer #3	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C)C(O)=C1)C2=O	3232.7	Semi standard non polar	33892256
Licoagroaurone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C)C(O)=C1)C2=O	3146.7	Semi standard non polar	33892256
Licoagroaurone,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O)C(O[Si](C)(C)C)=C1)C2=O	3158.4	Semi standard non polar	33892256
Licoagroaurone,2TMS,isomer #3	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C2=O	3177.7	Semi standard non polar	33892256
Licoagroaurone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C2=O	3146.9	Semi standard non polar	33892256
Licoagroaurone,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O)C(O)=C1)C2=O	3448.5	Semi standard non polar	33892256
Licoagroaurone,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C2=O	3497.0	Semi standard non polar	33892256
Licoagroaurone,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C2=O	3502.4	Semi standard non polar	33892256
Licoagroaurone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C2=O	3681.1	Semi standard non polar	33892256
Licoagroaurone,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C2=O	3681.8	Semi standard non polar	33892256
Licoagroaurone,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C2=O	3667.8	Semi standard non polar	33892256
Licoagroaurone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1O/C(=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C2=O	3835.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Licoagroaurone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4946000000-fe4e5cf172fe38250b31	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoagroaurone GC-MS (3 TMS) - 70eV, Positive	splash10-0udu-3090580000-fa098ae42b72d7991ab6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoagroaurone 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 - Licoagroaurone 10V, Positive-QTOF	splash10-000i-0539000000-efa42993b2749e2337cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 20V, Positive-QTOF	splash10-0avr-3894000000-5daf1933e0a0a01d1001	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 40V, Positive-QTOF	splash10-014r-4900000000-f34d2c4f270bd0bd4b3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 10V, Negative-QTOF	splash10-000i-0119000000-76db7486ae07657d2aee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 20V, Negative-QTOF	splash10-000i-0459000000-8b0382b4e6556e36d27a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 40V, Negative-QTOF	splash10-0avi-1921000000-a1fc555cb660e95cb32f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 10V, Negative-QTOF	splash10-000i-0019000000-36be3f244ff578a4a270	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 20V, Negative-QTOF	splash10-000i-0379000000-8675a43b574d247c90de	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 40V, Negative-QTOF	splash10-00bc-0391000000-d325e5f03220c0d2f6df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 10V, Positive-QTOF	splash10-0019-0049000000-0bd0a2d445ee612f311e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 20V, Positive-QTOF	splash10-001i-0290000000-2534d088c7eda9080298	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagroaurone 40V, Positive-QTOF	splash10-01ti-1960000000-5f33f70928c3a1415762	2021-09-24	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

FDB014047

KNApSAcK ID

C00014650

Chemspider ID

30777085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12069327

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Licoagroaurone (HMDB0035373)

MOL for HMDB0035373 (Licoagroaurone)

3D MOL for HMDB0035373 (Licoagroaurone)

3D SDF for HMDB0035373 (Licoagroaurone)

3D-SDF for HMDB0035373 (Licoagroaurone)

PDB for HMDB0035373 (Licoagroaurone)

3D PDB for HMDB0035373 (Licoagroaurone)

SMILES for HMDB0035373 (Licoagroaurone)

INCHI for HMDB0035373 (Licoagroaurone)

Structure for HMDB0035373 (Licoagroaurone)

3D Structure for HMDB0035373 (Licoagroaurone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra