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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:30:32 UTC

Update Date

2022-03-07 02:54:32 UTC

HMDB ID

HMDB0035501

Secondary Accession Numbers

HMDB35501

Metabolite Identification

Common Name

Licoagrochalcone B

Description

Licoagrochalcone B belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, licoagrochalcone b is considered to be a flavonoid. Licoagrochalcone B has been detected, but not quantified in, several different foods, such as black tea, herbs and spices, teas (Camellia sinensis), green tea, and red tea. This could make licoagrochalcone b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licoagrochalcone B.

Structure

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

HMDB0035501
     RDKit          3D
Licoagrochalcone B
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2648   -0.6161    1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361    0.2512    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -0.1412   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -0.7535   -1.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -1.0027   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -0.5952   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.9210   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -1.6304   -2.6411 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4734   -0.4301   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350    0.3505    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    0.8035    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8356    0.4753    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0010    0.9058    1.0282 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811   -0.3060   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.7479   -1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -1.1051   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -0.8487   -2.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -0.2304   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2576    0.1272    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    0.7786    1.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083    1.0392    1.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    0.6526    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331   -0.3500    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8307    1.8774    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5687    0.0263   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.4995    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.0206    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.9297    2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.6263   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893    0.0301   -0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.6443    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309    1.4133    1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3934    1.7896    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8508   -0.5796   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909   -1.3663   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808   -1.5921   -3.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.1465   -2.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.0817    1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.5416    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0018   -0.1887    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8384   -0.2851    2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -1.3933    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1172    2.5936   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3104    2.3678    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5262    1.5562   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 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
 22 23  1  0
 22 24  1  0
 22 25  1  0
 19  3  1  0
 15  9  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 24 45  1  0
M  END


  Mrv0541 05061308312D          

 25 27  0  0  0  0            999 V2000
    2.9559    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    2.8377    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
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
   -2.8579   -1.6500    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 13 12  2  0  0  0  0
 14  4  2  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  2  0  0  0  0
 20 15  2  0  0  0  0
 20 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 13  1  0  0  0  0
 22 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24  3  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035501

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC2=C1C=CC(C)(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O4/c1-21(2)13-12-17-19(25-21)11-7-15(20(17)24-3)6-10-18(23)14-4-8-16(22)9-5-14/h4-13,22H,1-3H3/b10-6+

> <INCHI_KEY>
BOJUBZPEDAAMPG-UXBLZVDNSA-N

> <FORMULA>
C21H20O4

> <MOLECULAR_WEIGHT>
336.3811

> <EXACT_MASS>
336.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.431949446115546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxyphenyl)-3-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
4.329712123666667

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.127824615007803

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.872864807288468

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58593353584902

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
99.71449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licoagrochalcone B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035501
     RDKit          3D
Licoagrochalcone B
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2648   -0.6161    1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361    0.2512    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -0.1412   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -0.7535   -1.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -1.0027   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -0.5952   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.9210   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -1.6304   -2.6411 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4734   -0.4301   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350    0.3505    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    0.8035    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8356    0.4753    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0010    0.9058    1.0282 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811   -0.3060   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.7479   -1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -1.1051   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -0.8487   -2.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -0.2304   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2576    0.1272    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    0.7786    1.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083    1.0392    1.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    0.6526    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331   -0.3500    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8307    1.8774    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5687    0.0263   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.4995    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.0206    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.9297    2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.6263   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893    0.0301   -0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.6443    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309    1.4133    1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3934    1.7896    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8508   -0.5796   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909   -1.3663   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808   -1.5921   -3.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.1465   -2.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.0817    1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.5416    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0018   -0.1887    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8384   -0.2851    2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -1.3933    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1172    2.5936   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3104    2.3678    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5262    1.5562   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 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
 22 23  1  0
 22 24  1  0
 22 25  1  0
 19  3  1  0
 15  9  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 24 45  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       5.518   3.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.528   5.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   24                                                            
CONECT    4    8   14                                                       
CONECT    5    9   14                                                       
CONECT    6   10   15                                                       
CONECT    7   11   15                                                       
CONECT    8    4   16                                                       
CONECT    9    5   16                                                       
CONECT   10    6   18                                                       
CONECT   11    7   19                                                       
CONECT   12   13   17                                                       
CONECT   13   12   21                                                       
CONECT   14    4    5   18                                                  
CONECT   15    6    7   20                                                  
CONECT   16    8    9   22                                                  
CONECT   17   12   19   20                                                  
CONECT   18   10   14   23                                                  
CONECT   19   11   17   25                                                  
CONECT   20   15   17   24                                                  
CONECT   21    1    2   13   25                                             
CONECT   22   16                                                            
CONECT   23   18                                                            
CONECT   24    3   20                                                       
CONECT   25   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0035501
HETATM    1  C1  UNL     1       0.265  -0.616   1.856  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.036   0.251   0.761  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.926  -0.141  -0.232  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.469  -0.753  -1.367  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.899  -1.003  -1.733  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.973  -0.595  -1.144  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.315  -0.921  -1.615  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.408  -1.630  -2.641  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.473  -0.430  -0.904  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.435   0.351   0.228  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.587   0.804   0.883  1.00  0.00           C  
HETATM   12  C10 UNL     1       6.836   0.475   0.405  1.00  0.00           C  
HETATM   13  O3  UNL     1       8.001   0.906   1.028  1.00  0.00           O  
HETATM   14  C11 UNL     1       6.881  -0.306  -0.727  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.762  -0.748  -1.366  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.493  -1.105  -2.279  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.814  -0.849  -2.037  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.233  -0.230  -0.887  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.258   0.127   0.030  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.744   0.779   1.232  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.008   1.039   1.492  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.037   0.653   0.506  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.933  -0.350   1.219  1.00  0.00           C  
HETATM   24  C21 UNL     1      -5.831   1.877   0.086  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.569   0.026  -0.649  1.00  0.00           O  
HETATM   26  H1  UNL     1       0.820  -1.500   1.463  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.896  -0.021   2.553  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.694  -0.930   2.297  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.069  -1.626  -2.629  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.889   0.030  -0.283  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.493   0.644   0.655  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.531   1.413   1.767  1.00  0.00           H  
HETATM   33  H8  UNL     1       8.393   1.790   0.729  1.00  0.00           H  
HETATM   34  H9  UNL     1       7.851  -0.580  -1.125  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.791  -1.366  -2.263  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.181  -1.592  -3.190  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.555  -1.147  -2.784  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.016   1.082   1.989  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.296   1.542   2.437  1.00  0.00           H  
HETATM   40  H15 UNL     1      -7.002  -0.189   0.927  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.838  -0.285   2.322  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.683  -1.393   0.935  1.00  0.00           H  
HETATM   43  H18 UNL     1      -5.117   2.594  -0.355  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.310   2.368   0.948  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.526   1.556  -0.694  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   16
CONECT    5    6    6   29
CONECT    6    7   30
CONECT    7    8    8    9
CONECT    9   10   10   15
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   13   14
CONECT   13   33
CONECT   14   15   15   34
CONECT   15   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   19   25
CONECT   19   20
CONECT   20   21   21   38
CONECT   21   22   39
CONECT   22   23   24   25
CONECT   23   40   41   42
CONECT   24   43   44   45
END

HMDB0035501
     RDKit          3D
Licoagrochalcone B
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2648   -0.6161    1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361    0.2512    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -0.1412   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -0.7535   -1.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -1.0027   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -0.5952   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.9210   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -1.6304   -2.6411 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4734   -0.4301   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350    0.3505    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    0.8035    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8356    0.4753    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0010    0.9058    1.0282 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8811   -0.3060   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.7479   -1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -1.1051   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -0.8487   -2.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -0.2304   -0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2576    0.1272    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    0.7786    1.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083    1.0392    1.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    0.6526    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331   -0.3500    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8307    1.8774    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5687    0.0263   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.4995    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.0206    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.9297    2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.6263   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893    0.0301   -0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.6443    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309    1.4133    1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3934    1.7896    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8508   -0.5796   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909   -1.3663   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808   -1.5921   -3.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.1465   -2.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.0817    1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.5416    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0018   -0.1887    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8384   -0.2851    2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -1.3933    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1172    2.5936   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3104    2.3678    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5262    1.5562   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 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
 22 23  1  0
 22 24  1  0
 22 25  1  0
 19  3  1  0
 15  9  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 24 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6'',6''-dimethylpyrano[2'',3'':4,3]-4'-hydroxy-2-methoxychalcone	HMDB

Chemical Formula

C₂₁H₂₀O₄

Average Molecular Weight

336.3811

Monoisotopic Molecular Weight

336.136159128

IUPAC Name

(2E)-1-(4-hydroxyphenyl)-3-(5-methoxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one

Traditional Name

licoagrochalcone B

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC2=C1C=CC(C)(C)O2

InChI Identifier

InChI=1S/C21H20O4/c1-21(2)13-12-17-19(25-21)11-7-15(20(17)24-3)6-10-18(23)14-4-8-16(22)9-5-14/h4-13,22H,1-3H3/b10-6+

InChI Key

BOJUBZPEDAAMPG-UXBLZVDNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retrochalcones

Alternative Parents

Substituents

Retrochalcone
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Anisole
Benzoyl
Styrene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120430 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035501)
Cell membrane (HMDB: HMDB0035501)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035501)

Source

Exogenous

Exogenous (HMDB: HMDB0035501)

Food

Food (HMDB: HMDB0035501)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0035501)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035501)

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	0.0014 g/L	ALOGPS
logP	4.68	ALOGPS
logP	4.33	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.71 m³·mol⁻¹	ChemAxon
Polarizability	37.43 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]+	182.681	30932474
DeepCCS	[M-H]-	180.323	30932474
DeepCCS	[M-2H]-	214.407	30932474
DeepCCS	[M+Na]+	189.636	30932474
AllCCS	[M+H]+	183.4	32859911
AllCCS	[M+H-H2O]+	180.0	32859911
AllCCS	[M+NH4]+	186.6	32859911
AllCCS	[M+Na]+	187.5	32859911
AllCCS	[M-H]-	183.8	32859911
AllCCS	[M+Na-2H]-	183.6	32859911
AllCCS	[M+HCOO]-	183.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.84 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3925 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2774.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	332.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	731.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	649.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1550.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1247.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	519.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	341.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licoagrochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC2=C1C=CC(C)(C)O2	4093.2	Standard polar	33892256
Licoagrochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC2=C1C=CC(C)(C)O2	2925.1	Standard non polar	33892256
Licoagrochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC2=C1C=CC(C)(C)O2	3147.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licoagrochalcone B,1TMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC2=C1C=CC(C)(C)O2	3105.7	Semi standard non polar	33892256
Licoagrochalcone B,1TBDMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC2=C1C=CC(C)(C)O2	3368.8	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 - Licoagrochalcone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2449000000-99e9f280cd06ff7a27a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoagrochalcone B GC-MS (1 TMS) - 70eV, Positive	splash10-0006-2219000000-65dfa145bc11c61ab790	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoagrochalcone B 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 - Licoagrochalcone B 10V, Positive-QTOF	splash10-000i-0019000000-0f0824d9d8f8b7aa237c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 20V, Positive-QTOF	splash10-00y1-2988000000-cdba9848c7c01433325f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 40V, Positive-QTOF	splash10-00di-6940000000-b41a2c1b903ebefeec1c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 10V, Negative-QTOF	splash10-000i-0119000000-e5d36b3f99908bf35914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 20V, Negative-QTOF	splash10-00kr-1249000000-ed488438d8ef0e6f1f2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 40V, Negative-QTOF	splash10-0gi3-3892000000-b0249b745be621116b1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 10V, Negative-QTOF	splash10-000i-0009000000-3fc8e7ce1e2d79ad2a06	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 20V, Negative-QTOF	splash10-052r-4049000000-1e750a1e0521fe75b7f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 40V, Negative-QTOF	splash10-001l-3139000000-52756f1400cd066c6942	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 10V, Positive-QTOF	splash10-000i-0009000000-7ccde74ebdd89b19fa68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 20V, Positive-QTOF	splash10-000l-0279000000-54e298b2ab7cdc76d7fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoagrochalcone B 40V, Positive-QTOF	splash10-00du-8934000000-70ac305690abc8ad78bd	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014188

KNApSAcK ID

C00014469

Chemspider ID

4477416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318989

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 Licoagrochalcone B (HMDB0035501)

MOL for HMDB0035501 (Licoagrochalcone B)

3D MOL for HMDB0035501 (Licoagrochalcone B)

3D SDF for HMDB0035501 (Licoagrochalcone B)

3D-SDF for HMDB0035501 (Licoagrochalcone B)

PDB for HMDB0035501 (Licoagrochalcone B)

3D PDB for HMDB0035501 (Licoagrochalcone B)

SMILES for HMDB0035501 (Licoagrochalcone B)

INCHI for HMDB0035501 (Licoagrochalcone B)

Structure for HMDB0035501 (Licoagrochalcone B)

3D Structure for HMDB0035501 (Licoagrochalcone B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra