NP-MRD: Showing NP-Card for (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate (NP0226513)

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Record Information

Version

2.0

Created at

2022-09-06 05:34:54 UTC

Updated at

2022-09-06 05:34:54 UTC

NP-MRD ID

NP0226513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate

Description

(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]Octan-3-yl 2-methylidenebutanedioate belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate is found in Schizanthus grahamii. Based on a literature review very few articles have been published on (1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]Octan-3-yl 2-methylidenebutanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207342D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062207342D          

 35 38  0  0  1  0            999 V2000
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    2.0626   -3.6086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8641   -3.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  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  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 19 21  1  6  0  0  0
  9 21  1  6  0  0  0
 21 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  6  0  0  0
 28 34  1  6  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C[C@H]2C[C@H](C[C@@H]1N2C)OC(=O)CC(=C)C(=O)O[C@H]1C[C@@H]2C[C@H](O)C[C@H]1N2C

> <INCHI_IDENTIFIER>
InChI=1S/C26H38N2O7/c1-6-14(2)25(31)34-23-11-17-9-19(13-21(23)28(17)5)33-24(30)7-15(3)26(32)35-22-10-16-8-18(29)12-20(22)27(16)4/h6,16-23,29H,3,7-13H2,1-2,4-5H3/b14-6-/t16-,17+,18-,19+,20+,21-,22-,23+/m0/s1

> <INCHI_KEY>
KOHKWULQOJFCAA-UUMHXYJISA-N

> <FORMULA>
C26H38N2O7

> <MOLECULAR_WEIGHT>
490.597

> <EXACT_MASS>
490.267901572

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.05308457307956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate

> <JCHEM_LOGP>
1.5997636033333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.155868109991907

> <JCHEM_PKA_STRONGEST_BASIC>
8.441608806544902

> <JCHEM_POLAR_SURFACE_AREA>
105.61

> <JCHEM_REFRACTIVITY>
128.58369999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.725  -3.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.725  -5.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.059  -5.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.393  -5.076   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.393  -3.536   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.726  -5.846   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.060  -5.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.332  -5.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.804  -5.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.367  -4.056   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -11.902  -3.941   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -12.770  -5.213   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -14.306  -5.098   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -12.102  -6.601   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.566  -6.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.969  -7.873   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.505  -7.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.597  -2.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.074  -2.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.945  -3.540   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -9.313  -3.775   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0     -10.647  -3.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.392  -5.846   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.392  -7.386   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.942  -5.076   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.276  -5.846   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.161  -7.382   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.290  -8.429   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.812  -8.200   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.582  -6.866   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.118  -6.981   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.020  -5.432   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.548  -4.978   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       3.850  -6.736   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       5.346  -6.371   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   10   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19    7                                                       
CONECT   21   19    9   22                                                  
CONECT   22   21                                                            
CONECT   23    2   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33   28   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,5R,6S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioic acid	Generator

Chemical Formula

C₂₆H₃₈N₂O₇

Average Mass

490.5970 Da

Monoisotopic Mass

490.26790 Da

IUPAC Name

(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate

Traditional Name

(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1R,3R,5S,6R)-8-methyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@H]2C[C@H](C[C@@H]1N2C)OC(=O)CC(=C)C(=O)O[C@H]1C[C@@H]2C[C@H](O)C[C@H]1N2C

InChI Identifier

InChI=1S/C26H38N2O7/c1-6-14(2)25(31)34-23-11-17-9-19(13-21(23)28(17)5)33-24(30)7-15(3)26(32)35-22-10-16-8-18(29)12-20(22)27(16)4/h6,16-23,29H,3,7-13H2,1-2,4-5H3/b14-6-/t16-,17+,18-,19+,20+,21-,22-,23+/m0/s1

InChI Key

KOHKWULQOJFCAA-UUMHXYJISA-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
Schizanthus grahamii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Tropane alkaloid
Fatty acid ester
Piperidine
Fatty acyl
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	1.6	ChemAxon
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	8.44	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.61 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.58 m³·mol⁻¹	ChemAxon
Polarizability	52.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162944104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate (NP0226513)

MOL for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

3D MOL for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

3D SDF for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

3D-SDF for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

PDB for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

3D PDB for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

SMILES for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

INCHI for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

Structure for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)

3D Structure for NP0226513 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (1r,3r,5s,6r)-8-methyl-6-{[(2z)-2-methylbut-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl 2-methylidenebutanedioate)