NP-MRD: Showing NP-Card for 3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone (NP0060679)

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Record Information

Version

2.0

Created at

2022-04-28 05:41:19 UTC

Updated at

2022-04-28 05:41:19 UTC

NP-MRD ID

NP0060679

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone

Description

Licoagrochalcone C 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 C is considered to be a flavonoid lipid molecule. Licoagrochalcone C is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Licoagrochalcone C has been detected, but not quantified in, herbs and spices and tea. 3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone is found in Glycyrrhiza glabra , Glycyrrhiza inflata and Glycyrrhiza uralensis . This could make licoagrochalcone C a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308262D          

 26 27  0  0  0  0            999 V2000
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    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
   -1.4289    5.7750    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145    2.0625    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
    0.7145   -0.4125    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
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -0.7145    4.5375    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
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    3.7125    0.0000 C   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
    0.0000    5.7750    0.0000 O   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
    2.1434    1.2375    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
  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  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 19  2  0  0  0  0
 21 14  2  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  3  1  0  0  0  0
 26 21  1  0  0  0  0
M  END


  Mrv0541 05061308262D          

 26 27  0  0  0  0            999 V2000
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    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
   -1.4289    5.7750    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145    2.0625    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
    0.7145   -0.4125    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
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -0.7145    4.5375    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
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    3.7125    0.0000 C   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
    0.0000    5.7750    0.0000 O   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
    2.1434    1.2375    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
  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  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 19  2  0  0  0  0
 21 14  2  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  3  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060679

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(\C=C\C(=O)C2=CC(O)=C(O)C=C2)C=CC(O)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(2)4-8-16-18(23)10-6-14(21(16)26-3)5-9-17(22)15-7-11-19(24)20(25)12-15/h4-7,9-12,23-25H,8H2,1-3H3/b9-5+

> <INCHI_KEY>
RDYZHQQZLIBKBP-WEVVVXLNSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.3964

> <EXACT_MASS>
354.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.027219392073285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(3,4-dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.550525077666666

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.965544324253333

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.93237061550191

> <JCHEM_PKA_STRONGEST_BASIC>
-4.862064539575966

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
103.52569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licoagrochalcone C

> <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      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   8.470   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       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   26                                                            
CONECT    4    8   13                                                       
CONECT    5    9   14                                                       
CONECT    6   10   14                                                       
CONECT    7   11   15                                                       
CONECT    8    4   16                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   19                                                       
CONECT   12   15   20                                                       
CONECT   13    1    2    4                                                  
CONECT   14    5    6   21                                                  
CONECT   15    7   12   17                                                  
CONECT   16    8   18   21                                                  
CONECT   17    9   15   22                                                  
CONECT   18   10   16   23                                                  
CONECT   19   11   20   24                                                  
CONECT   20   12   19   25                                                  
CONECT   21   14   16   26                                                  
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26    3   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
3',4,4'-Trihydroxy-2-methoxy-3-prenylchalcone	HMDB

Chemical Formula

C₂₁H₂₂O₅

Average Mass

354.3964 Da

Monoisotopic Mass

354.14672 Da

IUPAC Name

(2E)-1-(3,4-dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

Traditional Name

licoagrochalcone C

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(=O)C2=CC(O)=C(O)C=C2)C=CC(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C21H22O5/c1-13(2)4-8-16-18(23)10-6-14(21(16)26-3)5-9-17(22)15-7-11-19(24)20(25)12-15/h4-7,9-12,23-25H,8H2,1-3H3/b9-5+

InChI Key

RDYZHQQZLIBKBP-WEVVVXLNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

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
Phenoxy compound
Anisole
Benzoyl
Catechol
Methoxybenzene
Phenol ether
Aryl ketone
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120426 )

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	3.98	ALOGPS
logP	4.55	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.53 m³·mol⁻¹	ChemAxon
Polarizability	39.03 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

HMDB0035428

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014108

KNApSAcK ID

Not Available

Chemspider ID

4477417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318990

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone (NP0060679)

MOL for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

3D MOL for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

3D SDF for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

3D-SDF for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

PDB for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

3D PDB for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

SMILES for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

INCHI for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

Structure for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)

3D Structure for NP0060679 (3-Prenyl-4,3',4'-trihydroxy-2-methoxychalcone)