NP-MRD: Showing NP-Card for neosakuranetin (NP0168785)

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Record Information

Version

2.0

Created at

2022-09-03 04:38:46 UTC

Updated at

2022-09-03 04:38:46 UTC

NP-MRD ID

NP0168785

Secondary Accession Numbers

None

Natural Product Identification

Common Name

neosakuranetin

Description

(2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, (2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is considered to be a flavonoid lipid molecule (2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. neosakuranetin is found in Ononis natrix. It is generated by cyp2a6, cyp2c9, and cyp2c19 enzymes via an o-dealkylation reaction.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -6.6867    0.8812   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4621    1.1674   -1.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2383    0.7560   -0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843    1.0614   -1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.6704   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.0070   -1.4705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234   -0.0394    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.4530    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156   -1.1008    2.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -0.1737    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704   -0.6044    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853   -0.3813    0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -0.8675    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6923   -0.6951    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -0.0254   -0.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490    0.1315   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8647    0.4629   -1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559    0.2854   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046   -0.3401    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9324   -1.0228    2.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583    0.0640    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5545    1.0901    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4395    1.5884   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0557   -0.1413   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944    1.6119   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.5152   -2.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    0.3529   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -1.1364    1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2315   -1.3976    1.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5671   -1.0797    1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7404    0.9621   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    0.9971   -2.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308    0.6829   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -1.4076    2.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683   -0.1968    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 21  1  0
 21 19  2  0
 19 20  1  0
 18 12  1  0
 19  7  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
  6 26  1  0
  4 25  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 35  1  0
 20 34  1  0
M  END


  Mrv1652308221907122D          

 23 24  0  0  0  0            999 V2000
   -5.0013   -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
   -2.1434    3.7125    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    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    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
   -3.5724    2.0625    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
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
 10  2  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21 12  1  0  0  0  0
 22  4  1  0  0  0  0
 23  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168785

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=C(O)C=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-21-12-8-14(19)16(15(20)9-12)13(18)7-4-10-2-5-11(17)6-3-10/h2-9,17,19-20H,1H3/b7-4+

> <INCHI_KEY>
JGPQAWUEYNNXOH-QPJJXVBHSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.46638032683511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
4.121958078333334

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.199084943126513

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.954434739273272

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857665567904714

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
79.28290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neosakuranetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   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   4.620   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      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.335   4.620   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    5   10                                                       
CONECT    3    6   10                                                       
CONECT    4    7   10   22                                                  
CONECT    5    2   11                                                       
CONECT    6    3   11                                                       
CONECT    7    4   13   23                                                  
CONECT    8   12   14                                                       
CONECT    9   12   15                                                       
CONECT   10    2    3    4                                                  
CONECT   11    5    6   17                                                  
CONECT   12    8    9   21                                                  
CONECT   13    7   16   18                                                  
CONECT   14    8   16   19                                                  
CONECT   15    9   16   20                                                  
CONECT   16   13   14   15                                                  
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21    1   12                                                       
CONECT   22    4                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

(2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

neosakuranetin

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=C(O)C=C(OC)C=C1O

InChI Identifier

InChI=1S/C16H14O5/c1-21-12-8-14(19)16(15(20)9-12)13(18)7-4-10-2-5-11(17)6-3-10/h2-9,17,19-20H,1H3/b7-4+

InChI Key

JGPQAWUEYNNXOH-QPJJXVBHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ononis natrix	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
Anisole
Methoxybenzene
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Acryloyl-group
Vinylogous acid
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 (LMPK12120309 )

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	3.17	ALOGPS
logP	4.12	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.95	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	29.47 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

HMDB0132892

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9197661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11022479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for neosakuranetin (NP0168785)

MOL for NP0168785 (neosakuranetin)

3D MOL for NP0168785 (neosakuranetin)

3D SDF for NP0168785 (neosakuranetin)

3D-SDF for NP0168785 (neosakuranetin)

PDB for NP0168785 (neosakuranetin)

3D PDB for NP0168785 (neosakuranetin)

SMILES for NP0168785 (neosakuranetin)

INCHI for NP0168785 (neosakuranetin)

Structure for NP0168785 (neosakuranetin)

3D Structure for NP0168785 (neosakuranetin)