NP-MRD: Showing NP-Card for Echinatin (NP0054631)

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Record Information

Version

2.0

Created at

2022-04-28 00:55:25 UTC

Updated at

2022-04-28 00:55:25 UTC

NP-MRD ID

NP0054631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Echinatin

Description

Echinatin 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, echinatin is considered to be a flavonoid. Echinatin is found in Bauhinia manca, Dracaena draco, Glycyrrhiza aspera, Glycyrrhiza echinata , Glycyrrhiza glabra , Glycyrrhiza glara, Glycyrrhiza inflata , Glycyrrhiza pallidiflora and Glycyrrhiza uralensis . Echinatin was first documented in 2021 (PMID: 34598043). Based on a literature review a small amount of articles have been published on Echinatin (PMID: 35178925) (PMID: 35082510) (PMID: 34576274) (PMID: 34527599).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -1.9704   -2.4267    2.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216   -1.4708    1.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370   -0.6506    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731   -0.8058    1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216   -0.0157    0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0584   -0.2003    0.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2972    0.9299   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    1.0807   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.3034   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494    0.3776   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239    1.2072   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795    1.4370   -1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4408    2.4050   -2.4463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368    0.8928   -1.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170    1.2901   -1.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0540    0.8199   -1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262   -0.0723   -0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -0.5586   -0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1129   -0.4798    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364    0.0067   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -3.0863    2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079   -3.0857    1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4404   -1.9752    3.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0685   -1.5546    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4913    0.3186    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0444    1.5383   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6662    1.8357   -1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717   -0.3033    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7518    1.8660   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.9926   -2.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9407    1.1466   -2.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5582   -1.2163    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2171   -1.1780    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491   -0.3677    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 10 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
  8 27  1  0
  7 26  1  0
  6 25  1  0
  4 24  1  0
M  END


  Mrv1652304282202552D          

 20 21  0  0  0  0            999 V2000
    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
    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
   -0.0000   -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   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054631

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+

> <INCHI_KEY>
QJKMIJNRNRLQSS-WEVVVXLNSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.6237985158096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.1255233999999996

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.135519851844645

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8484757222381685

> <JCHEM_PKA_STRONGEST_BASIC>
-4.851614164027831

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.302

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
echinatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   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  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18   12   19                                                       
CONECT   19   18                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(2E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

echinatin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+

InChI Key

QJKMIJNRNRLQSS-WEVVVXLNSA-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
Bauhinia manca	Plant	KNApSAcK
Dracaena draco	LOTUS Database	35616633
Glycyrrhiza aspera	LOTUS Database	35616633
Glycyrrhiza echinata	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza glara	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza pallidiflora	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
Methoxybenzene
Benzoyl
Aryl ketone
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120431 )

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	3.41	ALOGPS
logP	3.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.85	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	4	ChemAxon
Refractivity	77.3 m³·mol⁻¹	ChemAxon
Polarizability	28.62 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

C00006922

Chemspider ID

4946739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu YL, Wang XY, Zhang H, Chen YL, Zhang ML, Chen XF, Niu L, Li WX, Tang JF: [Study on alleviating effect of Glycyrrhizae Radix et Rhizoma on Psoraleae Fructus-induced liver injury based on network pharmacology and cell experiments]. Zhongguo Zhong Yao Za Zhi. 2022 Jan;47(1):176-187. doi: 10.19540/j.cnki.cjcmm.20211025.401. [PubMed:35178925 ]
Wang Z, Xu G, Li Z, Xiao X, Tang J, Bai Z: NLRP3 Inflammasome Pharmacological Inhibitors in Glycyrrhiza for NLRP3-Driven Diseases Treatment: Extinguishing the Fire of Inflammation. J Inflamm Res. 2022 Jan 19;15:409-422. doi: 10.2147/JIR.S344071. eCollection 2022. [PubMed:35082510 ]
Mittal A, Kakkar R: The antioxidant potential of retrochalcones isolated from liquorice root: A comparative DFT study. Phytochemistry. 2021 Dec;192:112964. doi: 10.1016/j.phytochem.2021.112964. Epub 2021 Sep 29. [PubMed:34598043 ]
Xiao Y, Han F, Lee IS: Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites. Int J Mol Sci. 2021 Sep 18;22(18). pii: ijms221810109. doi: 10.3390/ijms221810109. [PubMed:34576274 ]
Hu Y, Liu M, Qin H, Lin H, An X, Shi Z, Song L, Yang X, Fan H, Tong Y: Artemether, Artesunate, Arteannuin B, Echinatin, Licochalcone B and Andrographolide Effectively Inhibit SARS-CoV-2 and Related Viruses In Vitro. Front Cell Infect Microbiol. 2021 Aug 30;11:680127. doi: 10.3389/fcimb.2021.680127. eCollection 2021. [PubMed:34527599 ]

Showing NP-Card for Echinatin (NP0054631)

MOL for NP0054631 (Echinatin)

3D MOL for NP0054631 (Echinatin)

3D SDF for NP0054631 (Echinatin)

3D-SDF for NP0054631 (Echinatin)

PDB for NP0054631 (Echinatin)

3D PDB for NP0054631 (Echinatin)

SMILES for NP0054631 (Echinatin)

INCHI for NP0054631 (Echinatin)

Structure for NP0054631 (Echinatin)

3D Structure for NP0054631 (Echinatin)