NP-MRD: Showing NP-Card for 4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one (NP0197884)

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Record Information

Version

2.0

Created at

2022-09-04 16:14:12 UTC

Updated at

2022-09-04 16:14:13 UTC

NP-MRD ID

NP0197884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one

Description

4-Methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]Tetradecan-12-ylidene]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as stemoamide-type alkaloids. These are alkaloids which include a tricyclic 2H-furo[3,2-c]pyrrolo[1,2-a]azepine nucleus. 4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one is found in Stemona curtisii and Stemona kerrii. Based on a literature review very few articles have been published on 4-methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]Tetradecan-12-ylidene]-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218142D          

 31 36  0  0  1  0            999 V2000
   -1.4772    0.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920    1.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    2.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    1.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1392    0.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9235   -0.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141   -1.0669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2164   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381    0.3202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805    0.1310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.9223    1.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 30 31  1  1  0  0  0
M  END

     RDKit          3D

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   -4.9108   -0.8761   -1.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042218142D          

 31 36  0  0  1  0            999 V2000
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   -0.6534    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2920    1.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0197884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)O\C1=C1\O[C@@]23CCCN4[C@@H](C[C@@H](O2)[C@H]4[C@H]3[C@@H]1C)[C@@H]1C[C@H](C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO7/c1-10-8-14(28-21(10)25)13-9-15-17-16-11(2)19(20-18(27-4)12(3)22(26)29-20)31-23(16,30-15)6-5-7-24(13)17/h10-11,13-17H,5-9H2,1-4H3/b20-19+/t10-,11-,13-,14-,15+,16+,17-,23+/m0/s1

> <INCHI_KEY>
VWLSPPQJJDUUFR-XXHVQFJZSA-N

> <FORMULA>
C23H29NO7

> <MOLECULAR_WEIGHT>
431.485

> <EXACT_MASS>
431.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.872917878379866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0^{1,10}.0^{5,9}]tetradecan-12-ylidene]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.5541344913333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.03448696844506

> <JCHEM_POLAR_SURFACE_AREA>
83.53000000000002

> <JCHEM_REFRACTIVITY>
110.7061

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0^{1,10}.0^{5,9}]tetradecan-12-ylidene]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.757   0.256   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.220   0.171   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.377   1.460   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.925   2.900   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.412   3.302   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.274   3.865   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.198   5.404   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.563   3.023   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.161   1.537   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.127   0.337   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.724  -1.149   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.013  -1.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.271  -0.413   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.813   1.173   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.384   1.559   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.671   0.598   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.244   0.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.390   1.273   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.231   2.805   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.639   3.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.961   4.935   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.668   2.283   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.199   2.442   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.895   0.951   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.423  -1.336   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.961  -2.097   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.489  -2.953   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.279  -0.825   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.213  -1.026   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.665   0.414   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.588   1.952   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   17   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   12                                                       
CONECT   28   26   16   29                                                  
CONECT   29   28   12   30                                                  
CONECT   30   29   10   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉NO₇

Average Mass

431.4850 Da

Monoisotopic Mass

431.19440 Da

IUPAC Name

4-methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0^{1,10}.0^{5,9}]tetradecan-12-ylidene]-2,5-dihydrofuran-2-one

Traditional Name

4-methoxy-3-methyl-5-[(1R,6S,8R,9R,10R,11S,12E)-11-methyl-6-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0^{1,10}.0^{5,9}]tetradecan-12-ylidene]furan-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)O\C1=C1\O[C@@]23CCCN4[C@@H](C[C@@H](O2)[C@H]4[C@H]3[C@@H]1C)[C@@H]1C[C@H](C)C(=O)O1

InChI Identifier

InChI=1S/C23H29NO7/c1-10-8-14(28-21(10)25)13-9-15-17-16-11(2)19(20-18(27-4)12(3)22(26)29-20)31-23(16,30-15)6-5-7-24(13)17/h10-11,13-17H,5-9H2,1-4H3/b20-19+/t10-,11-,13-,14-,15+,16+,17-,23+/m0/s1

InChI Key

VWLSPPQJJDUUFR-XXHVQFJZSA-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
Stemona curtisii	LOTUS Database	35616633
Stemona kerrii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stemoamide-type alkaloids. These are alkaloids which include a tricyclic 2H-furo[3,2-c]pyrrolo[1,2-a]azepine nucleus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stemoamide-type alkaloids

Alternative Parents

Substituents

Stemoamide backbone
Furofuran
Azepane
Ketal
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Dihydrofuran
Enol ester
Pyrrolidine
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.55	ChemAxon
pKa (Strongest Basic)	10.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.71 m³·mol⁻¹	ChemAxon
Polarizability	45.87 Å³	ChemAxon
Number of Rings	6	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

162891913

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one (NP0197884)

MOL for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

3D MOL for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

3D SDF for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

3D-SDF for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

PDB for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

3D PDB for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

SMILES for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

INCHI for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

Structure for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)

3D Structure for NP0197884 (4-methoxy-3-methyl-5-[(1r,6s,8r,9r,10r,11s,12e)-11-methyl-6-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-13,14-dioxa-5-azatetracyclo[6.5.1.0¹,¹⁰.0⁵,⁹]tetradecan-12-ylidene]furan-2-one)