NP-MRD: Showing NP-Card for 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate (NP0302437)

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Record Information

Version

2.0

Created at

2022-09-10 15:58:56 UTC

Updated at

2022-09-10 15:58:57 UTC

NP-MRD ID

NP0302437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate

Description

CHEMBL1195355 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. 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate is found in Datura stramonium. Based on a literature review very few articles have been published on CHEMBL1195355.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.2858    2.6077    0.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    1.4776   -0.1830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2671    1.3548    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770    2.1608    0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116    0.3906   -0.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378    0.3677    0.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8345    0.5732   -1.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2831    0.5882   -0.7386 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9666   -0.6722   -1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4491   -1.7226   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -0.9382    0.8504 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3300   -0.9307    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    0.3945    0.6878 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6797    0.5144    1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763    0.2676    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2367   -0.3159   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050   -1.4568   -0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0297   -2.0421    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672   -1.4550    1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.3186    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0721    2.3637    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516    3.5376    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    2.6855    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    1.7429   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    1.1819    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.2814   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6247    1.5056   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    1.4679   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -0.8486   -2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546   -0.5845   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544   -2.2805   -0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -2.4218    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -1.3585    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240   -1.7515    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -1.0321    1.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638   -0.1680    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4891    0.3327    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604    1.5402    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.1077   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6069   -1.9098   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6323   -2.9282    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672   -1.8874    2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9038    0.1416    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  8 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  6  1  0
 20 15  1  0
 13 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  6 25  1  1
 12 34  1  0
 12 35  1  0
 11 33  1  1
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
  8 28  1  1
  7 26  1  0
  7 27  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv1652309102217582D          

 20 22  0  0  0  0            999 V2000
    2.7880    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505    1.3508    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  0  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  0  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  0  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
    0.5690    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505    2.7798    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(=O)OC1CC2CCC(C1)N2C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,12,14-16H,8-11H2,1-2H3

> <INCHI_KEY>
ABQUDUAAINLKTQ-UHFFFAOYSA-N

> <FORMULA>
C17H23NO2

> <MOLECULAR_WEIGHT>
273.376

> <EXACT_MASS>
273.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.614911834273187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate

> <JCHEM_LOGP>
2.852012173333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.385562628854633

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
79.04170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.204   3.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.744   3.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.514   2.522   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.054   2.522   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.062   1.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.514   5.189   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.744   6.523   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.514   7.856   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.054   7.856   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.824   6.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.054   5.189   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    6                                                       
CONECT   13   11    8   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₃NO₂

Average Mass

273.3760 Da

Monoisotopic Mass

273.17288 Da

IUPAC Name

8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate

Traditional Name

8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C(=O)OC1CC2CCC(C1)N2C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H23NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,12,14-16H,8-11H2,1-2H3

InChI Key

ABQUDUAAINLKTQ-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
Datura stramonium	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

Tropane alkaloid
Monocyclic benzene moiety
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.85	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.04 m³·mol⁻¹	ChemAxon
Polarizability	30.61 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8576530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10401092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate (NP0302437)

MOL for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

3D MOL for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

3D SDF for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

3D-SDF for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

PDB for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

3D PDB for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

SMILES for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

INCHI for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

Structure for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)

3D Structure for NP0302437 (8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylpropanoate)