Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:53 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029514

Secondary Accession Numbers

HMDB29514

Metabolite Identification

Common Name

Licochalcone A

Description

Licochalcone A 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. Based on a literature review very few articles have been published on Licochalcone A.

Structure

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

HMDB0029514
     RDKit          3D
Licochalcone A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.8503    3.2341   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    2.4248   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6979    1.1517   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.4556   -2.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.6910   -1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1294    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -0.5331   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415   -1.4848    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.1447    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -1.7010    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483   -0.3755   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    0.5372   -0.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939   -0.0438   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940   -0.9707   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8430   -0.5516   -1.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0661    0.7499   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267    1.1570   -2.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    1.6538   -1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959    1.2760   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.7937    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -2.7593    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -3.0602    3.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.1629    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718   -0.1969    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.4075    1.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    4.1278    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    3.0328   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    2.6289    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.3843   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    1.6499   -1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    0.5700   -2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    1.0021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    1.0077   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339   -0.4189   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.2911   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -3.2271    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -2.4310    0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048   -1.9978   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6677   -1.2492   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187    1.1054   -3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2440    2.6887   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    2.0248   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -2.1775    4.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -3.7588    4.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724   -3.5571    3.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948   -1.3802    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    0.1767    2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END


  Mrv0541 05061304482D          

 25 26  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    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
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  2  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  5  1  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24 19  1  0  0  0  0
 25  4  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029514

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8-

> <INCHI_KEY>
KAZSKMJFUPEHHW-FLIBITNWSA-N

> <FORMULA>
C21H22O4

> <MOLECULAR_WEIGHT>
338.397

> <EXACT_MASS>
338.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.944569359578765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
4.74

> <JCHEM_LOGP>
4.811160349333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.90456438425105

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.830492476844746

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8519755505754985

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
100.61299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029514
     RDKit          3D
Licochalcone A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.8503    3.2341   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    2.4248   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6979    1.1517   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.4556   -2.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.6910   -1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1294    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -0.5331   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415   -1.4848    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.1447    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -1.7010    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483   -0.3755   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    0.5372   -0.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939   -0.0438   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940   -0.9707   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8430   -0.5516   -1.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0661    0.7499   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267    1.1570   -2.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    1.6538   -1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959    1.2760   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.7937    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -2.7593    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -3.0602    3.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.1629    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718   -0.1969    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.4075    1.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    4.1278    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    3.0328   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    2.6289    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.3843   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    1.6499   -1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    0.5700   -2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    1.0021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    1.0077   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339   -0.4189   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.2911   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -3.2271    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -2.4310    0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048   -1.9978   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6677   -1.2492   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187    1.1054   -3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2440    2.6887   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    2.0248   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -2.1775    4.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -3.7588    4.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724   -3.5571    3.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948   -1.3802    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    0.1767    2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  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       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -7.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770 -10.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   25                                                            
CONECT    5    1   21                                                       
CONECT    6    9   14                                                       
CONECT    7   10   14                                                       
CONECT    8   11   15                                                       
CONECT    9    6   16                                                       
CONECT   10    7   16                                                       
CONECT   11    8   18                                                       
CONECT   12   15   17                                                       
CONECT   13   19   20                                                       
CONECT   14    6    7   18                                                  
CONECT   15    8   12   20                                                  
CONECT   16    9   10   22                                                  
CONECT   17   12   19   21                                                  
CONECT   18   11   14   23                                                  
CONECT   19   13   17   24                                                  
CONECT   20   13   15   25                                                  
CONECT   21    2    3    5   17                                             
CONECT   22   16                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0029514
HETATM    1  C1  UNL     1      -3.850   3.234  -0.177  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.822   2.425  -0.043  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.698   1.152  -0.837  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.812   1.456  -2.006  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.039   0.691  -1.341  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.158   0.129   0.061  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.978  -0.533  -0.152  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.441  -1.485   0.659  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.816  -2.145   0.588  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.962  -1.701   0.230  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.248  -0.376  -0.175  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.383   0.537  -0.137  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.594  -0.044  -0.658  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.594  -0.971  -0.744  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.843  -0.552  -1.224  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.066   0.750  -1.598  1.00  0.00           C  
HETATM   17  O2  UNL     1       7.327   1.157  -2.079  1.00  0.00           O  
HETATM   18  C16 UNL     1       5.033   1.654  -1.497  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.796   1.276  -1.031  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.208  -1.794   1.817  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.742  -2.759   2.706  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.505  -3.060   3.850  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.375  -1.163   2.058  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.872  -0.197   1.197  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.066   0.407   1.505  1.00  0.00           O  
HETATM   26  H1  UNL     1      -3.892   4.128   0.411  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.653   3.033  -0.857  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.018   2.629   0.640  1.00  0.00           H  
HETATM   29  H4  UNL     1      -2.152   2.384  -2.505  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.756   1.650  -1.699  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.841   0.570  -2.682  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.881   1.002  -0.686  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.219   1.008  -2.401  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.034  -0.419  -1.344  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.509  -0.291  -1.123  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.803  -3.227   0.887  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.841  -2.431   0.240  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.505  -1.998  -0.477  1.00  0.00           H  
HETATM   39  H14 UNL     1       6.668  -1.249  -1.310  1.00  0.00           H  
HETATM   40  H15 UNL     1       7.519   1.105  -3.076  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.244   2.689  -1.805  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.017   2.025  -0.970  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.775  -2.177   4.447  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.899  -3.759   4.481  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.472  -3.557   3.574  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.995  -1.380   2.950  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.595   0.177   2.331  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   28
CONECT    3    4    5    6
CONECT    4   29   30   31
CONECT    5   32   33   34
CONECT    6    7    7   24
CONECT    7    8   35
CONECT    8    9   20   20
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   18
CONECT   17   40
CONECT   18   19   19   41
CONECT   19   42
CONECT   20   21   23
CONECT   21   22
CONECT   22   43   44   45
CONECT   23   24   24   46
CONECT   24   25
CONECT   25   47
END

HMDB0029514
     RDKit          3D
Licochalcone A
 47 48  0  0  0  0  0  0  0  0999 V2000
   -3.8503    3.2341   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    2.4248   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6979    1.1517   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.4556   -2.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.6910   -1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1294    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -0.5331   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415   -1.4848    0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.1447    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -1.7010    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483   -0.3755   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    0.5372   -0.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939   -0.0438   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940   -0.9707   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8430   -0.5516   -1.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0661    0.7499   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267    1.1570   -2.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    1.6538   -1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7959    1.2760   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.7937    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -2.7593    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -3.0602    3.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.1629    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718   -0.1969    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.4075    1.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925    4.1278    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    3.0328   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    2.6289    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.3843   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    1.6499   -1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    0.5700   -2.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    1.0021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    1.0077   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339   -0.4189   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.2911   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -3.2271    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -2.4310    0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048   -1.9978   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6677   -1.2492   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187    1.1054   -3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2440    2.6887   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    2.0248   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -2.1775    4.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -3.7588    4.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724   -3.5571    3.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948   -1.3802    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    0.1767    2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Dimethylallyl-4,4'-dihydroxy-6-methoxychalcone	HMDB
3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one, 9ci	HMDB
5-(1,1-Dimethylallyl)-4,4'-dihydroxy-2-methoxychalcone	HMDB
Licochalcone-a, synthetic	HMDB

Chemical Formula

C₂₁H₂₂O₄

Average Molecular Weight

338.397

Monoisotopic Molecular Weight

338.151809192

IUPAC Name

(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

58749-22-7

SMILES

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

InChI Identifier

InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8-

InChI Key

KAZSKMJFUPEHHW-FLIBITNWSA-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
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenylpropane
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Aryl ketone
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029514)

Cellular substructure

Membrane (HMDB: HMDB0029514)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029514)

Source

Endogenous

Endogenous (HMDB: HMDB0029514)

Plant

Plant (HMDB: HMDB0029514)

Exogenous

Food

Food (HMDB: HMDB0029514)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	101 - 102 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.37 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	4.74	ALOGPS
logP	4.81	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.61 m³·mol⁻¹	ChemAxon
Polarizability	36.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.237	30932474
DeepCCS	[M-H]-	183.879	30932474
DeepCCS	[M-2H]-	218.097	30932474
DeepCCS	[M+Na]+	193.246	30932474
AllCCS	[M+H]+	182.6	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	185.7	32859911
AllCCS	[M+Na]+	186.6	32859911
AllCCS	[M-H]-	183.3	32859911
AllCCS	[M+Na-2H]-	183.1	32859911
AllCCS	[M+HCOO]-	183.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licochalcone A	COC1=C(\C=C/C(=O)C2=CC=C(O)C=C2)C=C(C(O)=C1)C(C)(C)C=C	4225.6	Standard polar	33892256
Licochalcone A	COC1=C(\C=C/C(=O)C2=CC=C(O)C=C2)C=C(C(O)=C1)C(C)(C)C=C	2823.3	Standard non polar	33892256
Licochalcone A	COC1=C(\C=C/C(=O)C2=CC=C(O)C=C2)C=C(C(O)=C1)C(C)(C)C=C	3222.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licochalcone A,1TMS,isomer #1	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)=C(OC)C=C1O	3107.7	Semi standard non polar	33892256
Licochalcone A,1TMS,isomer #2	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O)C=C2)=C(OC)C=C1O[Si](C)(C)C	3084.9	Semi standard non polar	33892256
Licochalcone A,2TMS,isomer #1	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)=C(OC)C=C1O[Si](C)(C)C	3092.9	Semi standard non polar	33892256
Licochalcone A,1TBDMS,isomer #1	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(OC)C=C1O	3382.1	Semi standard non polar	33892256
Licochalcone A,1TBDMS,isomer #2	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O)C=C2)=C(OC)C=C1O[Si](C)(C)C(C)(C)C	3368.4	Semi standard non polar	33892256
Licochalcone A,2TBDMS,isomer #1	C=CC(C)(C)C1=CC(/C=C\C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(OC)C=C1O[Si](C)(C)C(C)(C)C	3591.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Licochalcone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2139000000-dd5ce01349b0a049596e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licochalcone A GC-MS (2 TMS) - 70eV, Positive	splash10-014i-1200900000-6f056fe7ac8d0f676d66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licochalcone A 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 - Licochalcone A 10V, Positive-QTOF	splash10-000i-0119000000-0a51f40550ed5ec31662	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 20V, Positive-QTOF	splash10-0g4r-6988000000-1d8184f09c04ea1287d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 40V, Positive-QTOF	splash10-0gi0-9620000000-6ed095cd55530005bea4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 10V, Negative-QTOF	splash10-000i-0119000000-da11738b507a0d3c769b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 20V, Negative-QTOF	splash10-00kr-1349000000-d3626b47e8fe11710eb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 40V, Negative-QTOF	splash10-00kf-7891000000-b2d96245724d0ae4c02e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 10V, Negative-QTOF	splash10-000i-0009000000-58aebbe019e7e30272d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 20V, Negative-QTOF	splash10-000i-1039000000-773f8a1d35597143325d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 40V, Negative-QTOF	splash10-0f79-2295000000-0ebd8672ece561c84e5d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 10V, Positive-QTOF	splash10-000i-0019000000-136e9e17a9180600a645	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 20V, Positive-QTOF	splash10-00dl-1494000000-55b38967e7349c9cae58	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone A 40V, Positive-QTOF	splash10-00dl-4941000000-9242418bf60def323fc9	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

FDB000649

KNApSAcK ID

C00007057

Chemspider ID

30776779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Licochalcone A

METLIN ID

Not Available

PubChem Compound

45934446

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810121

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 Licochalcone A (HMDB0029514)

MOL for HMDB0029514 (Licochalcone A)

3D MOL for HMDB0029514 (Licochalcone A)

3D SDF for HMDB0029514 (Licochalcone A)

3D-SDF for HMDB0029514 (Licochalcone A)

PDB for HMDB0029514 (Licochalcone A)

3D PDB for HMDB0029514 (Licochalcone A)

SMILES for HMDB0029514 (Licochalcone A)

INCHI for HMDB0029514 (Licochalcone A)

Structure for HMDB0029514 (Licochalcone A)

3D Structure for HMDB0029514 (Licochalcone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra