NP-MRD: Showing NP-Card for 16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate (NP0309756)

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Record Information

Version

2.0

Created at

2022-09-11 04:34:30 UTC

Updated at

2022-09-11 04:34:30 UTC

NP-MRD ID

NP0309756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate

Description

Oleanderolide 3-acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Oleanderolide 3-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, oleanderolide 3-acetate has been detected, but not quantified in, fruits. 16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate is found in Betula ermanii, Pieris japonica and Rhodomyrtus tomentosa. This could make oleanderolide 3-acetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241208402D          

 37 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241208402D          

 37 42  0  0  0  0            999 V2000
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    3.5582    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8552   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0302   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7003    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244   -0.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7003    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4349    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9163   -2.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349   -2.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -0.7733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 34  1  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 23  1  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
  9 11  1  0  0  0  0
  9 26  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 12 28  1  0  0  0  0
 13 14  1  0  0  0  0
 13 29  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
 17 19  1  0  0  0  0
 17 32  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 30  1  0  0  0  0
 21 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C(CCC3(C)C2CC(O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O5/c1-19(33)36-24-10-11-28(6)20(27(24,4)5)9-12-29(7)21(28)17-23(34)32-22-18-26(2,3)13-15-31(22,25(35)37-32)16-14-30(29,32)8/h20-24,34H,9-18H2,1-8H3

> <INCHI_KEY>
SFSFDBPTPLSWRM-UHFFFAOYSA-N

> <FORMULA>
C32H50O5

> <MOLECULAR_WEIGHT>
514.7364

> <EXACT_MASS>
514.36582471

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
60.307867198671275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
5.949759807666666

> <ALOGPS_LOGS>
-6.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.932089866845573

> <JCHEM_PKA_STRONGEST_BASIC>
-3.265903892241747

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
141.24640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.027  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.027  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.693  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.359  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.359  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.693  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.026  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.307  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.307  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.026  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.641  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.641   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.307   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.026   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.975  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.308  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.308   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.975   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.642   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.642   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.308   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.975   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.359   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.463  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.923  -5.184   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.307   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.641  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.152  -0.066   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.307   3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.538   5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.078   5.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.642   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.278   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.444  -3.898   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.861  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.278  -3.898   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.861  -1.443   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   24   25                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   23                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   27                                             
CONECT   12   11   13   18   28                                             
CONECT   13   12   14   29                                                  
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   32                                             
CONECT   18   12   17   22                                                  
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30   31                                             
CONECT   22   18   21                                                       
CONECT   23    5                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    9                                                            
CONECT   27   11                                                            
CONECT   28   12   32                                                       
CONECT   29   13                                                            
CONECT   30   21                                                            
CONECT   31   21                                                            
CONECT   32   17   28   33                                                  
CONECT   33   32                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
Oleanderolide 3-acetic acid	Generator
16-Hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetic acid	Generator

Chemical Formula

C₃₂H₅₀O₅

Average Mass

514.7364 Da

Monoisotopic Mass

514.36582 Da

IUPAC Name

16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate

Traditional Name

16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C(CCC3(C)C2CC(O)C24OC(=O)C5(CCC(C)(C)CC25)CCC34C)C1(C)C

InChI Identifier

InChI=1S/C32H50O5/c1-19(33)36-24-10-11-28(6)20(27(24,4)5)9-12-29(7)21(28)17-23(34)32-22-18-26(2,3)13-15-31(22,25(35)37-32)16-14-30(29,32)8/h20-24,34H,9-18H2,1-8H3

InChI Key

SFSFDBPTPLSWRM-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
Betula ermanii	LOTUS Database	35616633
Pieris japonica	LOTUS Database	35616633
Rhodomyrtus tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Not Available

Substituents

Not Available

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	5.76	ALOGPS
logP	5.95	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	141.25 m³·mol⁻¹	ChemAxon
Polarizability	60.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034647

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013171

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

85319558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate (NP0309756)

MOL for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

3D MOL for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

3D SDF for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

3D-SDF for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

PDB for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

3D PDB for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

SMILES for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

INCHI for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

Structure for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)

3D Structure for NP0309756 (16-hydroxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-10-yl acetate)