NP-MRD: Showing NP-Card for Licodione (NP0054693)

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Record Information

Version

2.0

Created at

2022-04-28 00:58:11 UTC

Updated at

2022-04-28 00:58:11 UTC

NP-MRD ID

NP0054693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Licodione

Description

Licodione belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, licodione is considered to be a flavonoid lipid molecule. Licodione is found in Glycyrrhiza echinata , Glycyrrhiza pallidiflora and Medicago sativa . Licodione was first documented in 1997 (PMID: 9055445). Licodione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 10540749).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    0.8691   -2.3382   -0.9829 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216   -1.2317   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -0.2782   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -0.8310   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2845   -1.9643   -0.9245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4931   -0.0769   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3744    1.1982    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759    1.9699    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467    1.5154    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584    2.3180    0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    0.2796   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7544   -0.5207   -0.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0396   -1.7379   -0.9638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5093   -0.8576   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    0.3551    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795    0.7049    0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2009   -0.1592    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5443    0.1514    0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -1.3743   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390   -1.7120   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306   -0.0565    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396    0.6741   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    1.5312    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    2.9450    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2093    2.9653    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8817   -0.0731   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -2.3972   -1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877    1.0380    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4731    1.6521    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7481    1.0624    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6730   -2.0610   -0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -2.6911   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 20  1  0
 20 19  2  0
 14  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 19 17  1  0
 12  6  1  0
 18 30  1  0
 16 29  1  0
 15 28  1  0
 20 32  1  0
 19 31  1  0
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
M  END


  Mrv1533004251523522D          

 20 21  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 O   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
    2.1434   -3.7125    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   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   -6.1875    0.0000 C   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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    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
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C(=O)CC(=O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-10-3-1-9(2-4-10)13(18)8-15(20)12-6-5-11(17)7-14(12)19/h1-7,16-17,19H,8H2

> <INCHI_KEY>
QIEKMEBGIJSGGB-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.85842179772741

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane-1,3-dione

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.916664864666666

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.092916304427204

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.486502550659559

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912227571488654

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
72.5647

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licodione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   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  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.000 -12.320   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  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)propane-1,3-dione	Kegg

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane-1,3-dione

Traditional Name

licodione

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(=O)CC(=O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C15H12O5/c16-10-3-1-9(2-4-10)13(18)8-15(20)12-6-5-11(17)7-14(12)19/h1-7,16-17,19H,8H2

InChI Key

QIEKMEBGIJSGGB-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 echinata	Plant	KNApSAcK
Glycyrrhiza pallidiflora	Plant	KNApSAcK
Medicago sativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones 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

Retro-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Retro-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Phenylketone
Benzoyl
Resorcinol
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:18131 )
aromatic ketone (CHEBI:18131 )
beta-diketone (CHEBI:18131 )
dihydrochalcones (CHEBI:18131 )
Chalcones and dihydrochalcones (C01592 )
Chalcones and dihydrochalcones (LMPK12120396 )

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	2.64	ALOGPS
logP	2.92	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.56 m³·mol⁻¹	ChemAxon
Polarizability	26.86 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006994

Chemspider ID

Not Available

KEGG Compound ID

C01592

BioCyc ID

LICODIONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439528

PDB ID

Not Available

ChEBI ID

18131

Good Scents ID

Not Available

References

General References

Nakamura K, Akashi T, Aoki T, Kawaguchi K, Ayabe S: Induction of isoflavonoid and retrochalcone branches of the flavonoid pathway in cultured Glycyrrhiza echinata cells treated with yeast extract. Biosci Biotechnol Biochem. 1999 Sep;63(9):1618-20. doi: 10.1271/bbb.63.1618. [PubMed:10540749 ]
Ichimura M, Furuno T, Takahashi T, Dixon RA, Ayabe S: Enzymic O-methylation of isoliquiritigenin and licodione in alfalfa and licorice cultures. Phytochemistry. 1997 Mar;44(6):991-5. doi: 10.1016/s0031-9422(96)00670-x. [PubMed:9055445 ]

Showing NP-Card for Licodione (NP0054693)

MOL for NP0054693 (Licodione)

3D MOL for NP0054693 (Licodione)

3D SDF for NP0054693 (Licodione)

3D-SDF for NP0054693 (Licodione)

PDB for NP0054693 (Licodione)

3D PDB for NP0054693 (Licodione)

SMILES for NP0054693 (Licodione)

INCHI for NP0054693 (Licodione)

Structure for NP0054693 (Licodione)

3D Structure for NP0054693 (Licodione)