NP-MRD: Showing NP-Card for (1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate (NP0244357)

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Record Information

Version

2.0

Created at

2022-09-07 05:07:56 UTC

Updated at

2022-09-07 05:07:57 UTC

NP-MRD ID

NP0244357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate

Description

(1R,5R)-8-methyl-8-azabicyclo[3.2.1]Octan-1-yl 2-phenylacetate 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. (1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate is found in Datura stramonium. Based on a literature review very few articles have been published on (1R,5R)-8-methyl-8-azabicyclo[3.2.1]Octan-1-yl 2-phenylacetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072207072D          

 19 21  0  0  1  0            999 V2000
   -0.2175    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075    0.8158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.1110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6436    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    1.7427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6557    2.5470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    3.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0488    2.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769    3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6816    4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    5.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    5.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912    5.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747    4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4700    4.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2CC[C@@]1(CCC2)OC(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO2/c1-17-14-8-5-10-16(17,11-9-14)19-15(18)12-13-6-3-2-4-7-13/h2-4,6-7,14H,5,8-12H2,1H3/t14-,16-/m1/s1

> <INCHI_KEY>
FPAXRIZNMBFUFU-GDBMZVCRSA-N

> <FORMULA>
C16H21NO2

> <MOLECULAR_WEIGHT>
259.349

> <EXACT_MASS>
259.15722892

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.022751522267555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate

> <JCHEM_LOGP>
3.194245460333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.267208521687726

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
74.57300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl phenylacetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.406   1.523   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.134   1.523   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.567  -0.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.068   0.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.736   1.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.068   2.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.567   3.253   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.224   4.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.353   5.802   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.824   5.348   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.010   7.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.139   8.351   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.796   9.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.925  10.900   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.397  10.446   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.740   8.944   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.611   7.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.363   2.293   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.363   0.753   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8   18                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    7   19                                                       
CONECT   19   18    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
(1R,5R)-8-Methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetic acid	Generator

Chemical Formula

C₁₆H₂₁NO₂

Average Mass

259.3490 Da

Monoisotopic Mass

259.15723 Da

IUPAC Name

(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate

Traditional Name

(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl phenylacetate

CAS Registry Number

Not Available

SMILES

CN1[C@H]2CC[C@@]1(CCC2)OC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C16H21NO2/c1-17-14-8-5-10-16(17,11-9-14)19-15(18)12-13-6-3-2-4-7-13/h2-4,6-7,14H,5,8-12H2,1H3/t14-,16-/m1/s1

InChI Key

FPAXRIZNMBFUFU-GDBMZVCRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Carboxylic acid ester
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
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	3.19	ChemAxon
pKa (Strongest Basic)	4.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.57 m³·mol⁻¹	ChemAxon
Polarizability	29.02 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

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

69566372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate (NP0244357)

MOL for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

3D MOL for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

3D SDF for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

3D-SDF for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

PDB for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

3D PDB for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

SMILES for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

INCHI for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

Structure for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)

3D Structure for NP0244357 ((1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-1-yl 2-phenylacetate)