NP-MRD: Showing NP-Card for 3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin (NP0056810)

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Record Information

Version

2.0

Created at

2022-04-28 02:27:43 UTC

Updated at

2022-04-28 02:27:43 UTC

NP-MRD ID

NP0056810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin

Description

Glycyrin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, glycyrin is considered to be a flavonoid lipid molecule. Glycyrin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Glycyrin has been detected, but not quantified in, root vegetables. 3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin is found in Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza sp. and Glycyrrhiza uralensis . 3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin was first documented in 2001 (PMID: 11575586). This could make glycyrin a potential biomarker for the consumption of these foods (PMID: 12127165) (PMID: 14608046) (PMID: 14643306).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307182D          

 28 30  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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    2.4750    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
   -2.1434    3.7125    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
    2.1434    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    1.2375    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  2  0  0  0  0
 19 11  2  0  0  0  0
 19 15  1  0  0  0  0
 20 11  1  0  0  0  0
 20 17  2  0  0  0  0
 21 15  2  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 23 13  1  0  0  0  0
 24 18  1  0  0  0  0
 25 22  2  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 21  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -3.5491    3.0668   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489    1.6942   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9564    1.2557   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715    2.0921   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465    1.6311   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    2.5051   -0.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    2.0596    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    2.8451    0.1100 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358    0.7028    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954    0.1803    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368    0.5552   -0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5168    0.0452   -0.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9144   -0.8762    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2129   -1.4137    0.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9946   -1.2503    1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -0.7351    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8235   -1.1533    2.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9100   -0.2099    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258    0.2836   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -0.6287   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -1.9635   -0.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -2.7966   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -0.1051   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8270   -1.0754   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0895   -0.4374   -0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1507   -0.4429    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0954   -1.0902    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4264    0.2068   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5567    3.2010   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6185    3.4607    0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8217    3.7019   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    3.1571   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631    1.2735   -1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2543    0.3330   -1.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9413   -0.9361    0.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2835   -1.9660    1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -0.7951    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.2637    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379   -2.2621   -2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130   -3.6282   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -3.3095   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.7936   -1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -1.6634    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1747    0.0450   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9878   -0.7987    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1510   -0.7294    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1232   -2.1863    1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4063    1.2733    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5584    0.2094   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659   -0.2684    0.2320 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 19  2  0
 19 18  1  0
 18  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  9 10  1  0
 10 16  2  0
 16 17  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23  3  1  0
  6  5  1  0
 11 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
 18 38  1  0
 17 37  1  0
 15 36  1  0
 14 35  1  0
 12 34  1  0
 11 33  1  0
 22 39  1  0
 22 40  1  0
 22 41  1  0
 24 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
M  END


  Mrv0541 05061307182D          

 28 30  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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    2.4750    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
   -2.1434    3.7125    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
    2.1434    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    1.2375    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  2  0  0  0  0
 19 11  2  0  0  0  0
 19 15  1  0  0  0  0
 20 11  1  0  0  0  0
 20 17  2  0  0  0  0
 21 15  2  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 23 13  1  0  0  0  0
 24 18  1  0  0  0  0
 25 22  2  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 21  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C(C(=O)O2)C2=C(O)C=C(O)C=C2)C(OC)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O6/c1-12(2)5-7-15-19(26-3)11-20-17(21(15)27-4)10-16(22(25)28-20)14-8-6-13(23)9-18(14)24/h5-6,8-11,23-24H,7H2,1-4H3

> <INCHI_KEY>
FWWGXZYUURXJLK-UHFFFAOYSA-N

> <FORMULA>
C22H22O6

> <MOLECULAR_WEIGHT>
382.4065

> <EXACT_MASS>
382.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.0383591840703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
4.257541235333333

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.898809249655114

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.492767024733585

> <JCHEM_PKA_STRONGEST_BASIC>
-4.562823264845932

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
107.13169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycyrin

> <JCHEM_VEBER_RULE>
0

$$$$

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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5    7   12                                                       
CONECT    6    8   13                                                       
CONECT    7    5   15                                                       
CONECT    8    6   14                                                       
CONECT    9   13   18                                                       
CONECT   10   16   17                                                       
CONECT   11   19   20                                                       
CONECT   12    1    2    5                                                  
CONECT   13    6    9   23                                                  
CONECT   14    8   16   18                                                  
CONECT   15    7   19   21                                                  
CONECT   16   10   14   22                                                  
CONECT   17   10   20   21                                                  
CONECT   18    9   14   24                                                  
CONECT   19   11   15   26                                                  
CONECT   20   11   17   28                                                  
CONECT   21   15   17   27                                                  
CONECT   22   16   25   28                                                  
CONECT   23   13                                                            
CONECT   24   18                                                            
CONECT   25   22                                                            
CONECT   26    3   19                                                       
CONECT   27    4   21                                                       
CONECT   28   20   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
3-(2',4'-Dihydroxyphenyl)-5,7-dimethoxy-2-isopentenylcoumarin	ChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one	ChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin	ChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₂₂H₂₂O₆

Average Mass

382.4065 Da

Monoisotopic Mass

382.14164 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

glycyrin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C(C(=O)O2)C2=C(O)C=C(O)C=C2)C(OC)=C1CC=C(C)C

InChI Identifier

InChI=1S/C22H22O6/c1-12(2)5-7-15-19(26-3)11-20-17(21(15)27-4)10-16(22(25)28-20)14-8-6-13(23)9-18(14)24/h5-6,8-11,23-24H,7H2,1-4H3

InChI Key

FWWGXZYUURXJLK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza sp.	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Hydroxyisoflavonoids

Direct Parent

Hydroxyisoflavonoids

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflav-3-enone skeleton
Coumarin
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:69086 )
coumarins (CHEBI:69086 )
hydroxyisoflavans (CHEBI:69086 )
Other Flavonoids (LMPK12160017 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	4.29	ALOGPS
logP	4.26	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.13 m³·mol⁻¹	ChemAxon
Polarizability	41.04 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

External Links

HMDB ID

HMDB0033712

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011830

KNApSAcK ID

C00009785

Chemspider ID

421867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

480787

PDB ID

Not Available

ChEBI ID

69086

Good Scents ID

Not Available

References

General References

Fukai T, Marumo A, Kaitou K, Kanda T, Terada S, Nomura T: Anti-Helicobacter pylori flavonoids from licorice extract. Life Sci. 2002 Aug 9;71(12):1449-63. doi: 10.1016/s0024-3205(02)01864-7. [PubMed:12127165 ]
Tanaka Y, Kikuzaki H, Fukuda S, Nakatani N: Antibacterial compounds of licorice against upper airway respiratory tract pathogens. J Nutr Sci Vitaminol (Tokyo). 2001 Jun;47(3):270-3. doi: 10.3177/jnsv.47.270. [PubMed:11575586 ]
Mae T, Kishida H, Nishiyama T, Tsukagawa M, Konishi E, Kuroda M, Mimaki Y, Sashida Y, Takahashi K, Kawada T, Nakagawa K, Kitahara M: A licorice ethanolic extract with peroxisome proliferator-activated receptor-gamma ligand-binding activity affects diabetes in KK-Ay mice, abdominal obesity in diet-induced obese C57BL mice and hypertension in spontaneously hypertensive rats. J Nutr. 2003 Nov;133(11):3369-77. doi: 10.1093/jn/133.11.3369. [PubMed:14608046 ]
Kuroda M, Mimaki Y, Sashida Y, Mae T, Kishida H, Nishiyama T, Tsukagawa M, Konishi E, Takahashi K, Kawada T, Nakagawa K, Kitahara M: Phenolics with PPAR-gamma ligand-binding activity obtained from licorice (Glycyrrhiza uralensis roots) and ameliorative effects of glycyrin on genetically diabetic KK-A(y) mice. Bioorg Med Chem Lett. 2003 Dec 15;13(24):4267-72. doi: 10.1016/j.bmcl.2003.09.052. [PubMed:14643306 ]

Showing NP-Card for 3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin (NP0056810)

MOL for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

3D MOL for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

3D SDF for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

3D-SDF for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

PDB for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

3D PDB for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

SMILES for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

INCHI for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

Structure for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)

3D Structure for NP0056810 (3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin)