NP-MRD: Showing NP-Card for (1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate (NP0289921)

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Record Information

Version

2.0

Created at

2022-09-09 20:20:43 UTC

Updated at

2022-09-09 20:20:44 UTC

NP-MRD ID

NP0289921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate

Description

(1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate is found in Hyoscyamus albus and Solandra grandiflora.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.8421   -0.3691    1.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443   -0.2810    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.0679   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044    0.0801   -1.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6891    0.0177   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3647    0.2198   -2.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -0.1196   -0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -0.0461   -0.3849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3555    1.1176    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    1.2533   -0.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7188    0.9376    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6172   -0.5708    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438   -0.9891   -0.3341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4704   -1.2879   -0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697    0.2030   -1.1855 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798    0.0998    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075   -1.3855    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    0.2012    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6364   -0.3880    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7331    1.0404   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9555   -0.7405   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192    0.1729   -2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    0.1388   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153    0.9644    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540    2.0250    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    2.2624   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7397    1.2523    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    1.4363    1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6232   -1.0374    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927   -0.8775    1.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4679   -1.8306   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947   -1.6300    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2145   -2.1004   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0334    0.2990   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 14  8  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  6
  9 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 15 34  1  0
M  END


  Mrv1652309092222202D          

 15 16  0  0  1  0            999 V2000
    6.0880   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -0.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  6  0  0  0
 10 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0289921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO2/c1-3-8(2)12(14)15-11-6-9-4-5-10(7-11)13-9/h3,9-11,13H,4-7H2,1-2H3/b8-3+/t9-,10+,11+

> <INCHI_KEY>
KLFGVBUPYUSQKV-YBOYPCLQSA-N

> <FORMULA>
C12H19NO2

> <MOLECULAR_WEIGHT>
209.289

> <EXACT_MASS>
209.141578856

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.224674714277782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5S)-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.863449962333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.016189662626598

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
59.1289

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S)-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      11.364  -1.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.824  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.054  -0.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.824   1.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.514  -0.146   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.744  -1.480   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₉NO₂

Average Mass

209.2890 Da

Monoisotopic Mass

209.14158 Da

IUPAC Name

(1R,3S,5S)-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,3S,5S)-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2

InChI Identifier

InChI=1S/C12H19NO2/c1-3-8(2)12(14)15-11-6-9-4-5-10(7-11)13-9/h3,9-11,13H,4-7H2,1-2H3/b8-3+/t9-,10+,11+

InChI Key

KLFGVBUPYUSQKV-YBOYPCLQSA-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
Hyoscyamus albus	LOTUS Database	35616633
Solandra grandiflora	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.86	ChemAxon
pKa (Strongest Basic)	11.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.13 m³·mol⁻¹	ChemAxon
Polarizability	23.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate (NP0289921)

MOL for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

PDB for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

Structure for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0289921 ((1r,3s,5s)-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)