NP-MRD: Showing NP-Card for 3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one (NP0315358)

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Record Information

Version

2.0

Created at

2022-09-11 13:57:11 UTC

Updated at

2022-09-11 13:57:11 UTC

NP-MRD ID

NP0315358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

Description

3-(4-Hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. 3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one is found in Citrus japonica and Paronychia argentea. 3-(4-Hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501492D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201501492D          

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    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 34 40  1  0  0  0  0
 29 41  2  0  0  0  0
 12 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)C1=C(O)C(C(=O)CCC2=CC=C(O)C=C2)=C(O)C(C2OC(CO)C(O)C(O)C2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O15/c28-7-12-17(32)22(37)24(39)26(41-12)15-19(34)14(11(31)6-3-9-1-4-10(30)5-2-9)20(35)16(21(15)36)27-25(40)23(38)18(33)13(8-29)42-27/h1-2,4-5,12-13,17-18,22-30,32-40H,3,6-8H2

> <INCHI_KEY>
WAWHTTXPRUWFCZ-UHFFFAOYSA-N

> <FORMULA>
C27H34O15

> <MOLECULAR_WEIGHT>
598.554

> <EXACT_MASS>
598.189770395

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.851356945243744

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

> <ALOGPS_LOGP>
-1.08

> <JCHEM_LOGP>
-1.619101277333333

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.013066096519601

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1233549898031026

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491264769120804

> <JCHEM_POLAR_SURFACE_AREA>
278.28999999999996

> <JCHEM_REFRACTIVITY>
139.94389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.005  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.005  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   41                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   15   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   41                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34                                                       
CONECT   41   29   12   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₅

Average Mass

598.5540 Da

Monoisotopic Mass

598.18977 Da

IUPAC Name

3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

Traditional Name

3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C(C(=O)CCC2=CC=C(O)C=C2)=C(O)C(C2OC(CO)C(O)C(O)C2O)=C1O

InChI Identifier

InChI=1S/C27H34O15/c28-7-12-17(32)22(37)24(39)26(41-12)15-19(34)14(11(31)6-3-9-1-4-10(30)5-2-9)20(35)16(21(15)36)27-25(40)23(38)18(33)13(8-29)42-27/h1-2,4-5,12-13,17-18,22-30,32-40H,3,6-8H2

InChI Key

WAWHTTXPRUWFCZ-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, 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
Citrus japonica	LOTUS Database	35616633
Paronychia argentea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone 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'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Phenolic glycoside
Alkyl-phenylketone
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Acylphloroglucinol derivative
Butyrophenone
Phloroglucinol derivative
Benzenetriol
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Polyol
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.1	ALOGPS
logP	-1.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	278.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.94 m³·mol⁻¹	ChemAxon
Polarizability	58.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74819290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one (NP0315358)

MOL for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

3D MOL for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

3D SDF for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

3D-SDF for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

PDB for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

3D PDB for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

SMILES for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

INCHI for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

Structure for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)

3D Structure for NP0315358 (3-(4-hydroxyphenyl)-1-{2,4,6-trihydroxy-3,5-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one)