NP-MRD: Showing NP-Card for 3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone (NP0138315)

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Record Information

Version

1.0

Created at

2022-05-31 17:54:53 UTC

Updated at

2022-05-31 17:54:53 UTC

NP-MRD ID

NP0138315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone

Description

2,4'-Dihydroxy-4,6-dimethoxydihydrochalcone 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, 2,4'-dihydroxy-4,6-dimethoxydihydrochalcone is considered to be a flavonoid lipid molecule. 2,4'-Dihydroxy-4,6-dimethoxydihydrochalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.8579   -1.5578   -0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8086   -1.2808   -1.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -0.5784   -1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6559   -0.3128   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317    0.3920   -1.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326    0.6377   -2.8188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966    0.8479   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702    1.5949   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    0.6248   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    1.3332    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004    2.5846    0.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4842    0.6131    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -0.7400    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -1.3786    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9340   -0.6749    0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1428   -1.3295    1.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319    0.6948    0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276    1.3319    0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    0.5928    0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.0595    1.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2937    0.7839    2.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241   -0.1165   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3306   -0.5915   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4961   -2.1100    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6538   -2.1484   -1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -0.6513   -3.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    0.3157   -3.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0795    2.3803   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    2.0783    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305   -0.0501    0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664    0.0165   -1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7186   -1.3102    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648   -2.4663    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7450   -1.4601    0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125    1.2512    1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    2.4104    0.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280    1.1980    2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288    1.1907    3.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -0.3213    2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799   -0.2957    0.5996 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  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 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
  7 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22  3  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
M  END


  Mrv1533004171500132D          

 22 23  0  0  0  0            999 V2000
    2.1434   -1.2375    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
    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
    4.2868   -4.1250    0.0000 O   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
    2.8579   -4.9500    0.0000 C   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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138315

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-21-13-9-16(20)14(17(10-13)22-2)7-8-15(19)11-3-5-12(18)6-4-11/h3-6,9-10,18,20H,7-8H2,1-2H3

> <INCHI_KEY>
KTMWYIVORZZVMV-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.011593963656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
2.887328644666666

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.306924265218587

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.763281909669324

> <JCHEM_PKA_STRONGEST_BASIC>
-4.550508610232011

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
82.67190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   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  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  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    7   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one

Traditional Name

3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one

CAS Registry Number

151752-07-7

SMILES

COC1=CC(O)=C(CCC(=O)C2=CC=C(O)C=C2)C(OC)=C1

InChI Identifier

InChI=1S/C17H18O5/c1-21-13-9-16(20)14(17(10-13)22-2)7-8-15(19)11-3-5-12(18)6-4-11/h3-6,9-10,18,20H,7-8H2,1-2H3

InChI Key

KTMWYIVORZZVMV-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

Not Available

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

Retro-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenylketone
Anisole
Benzoyl
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120607 )

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	3.13	ALOGPS
logP	2.89	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.67 m³·mol⁻¹	ChemAxon
Polarizability	32.01 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607735

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone (NP0138315)

MOL for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

3D MOL for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

3D SDF for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

3D-SDF for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

PDB for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

3D PDB for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

SMILES for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

INCHI for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

Structure for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)

3D Structure for NP0138315 (3-(2-Hydroxy-4,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone)