NP-MRD: Showing NP-Card for 3alpha-Phenylacetoxytropane (NP0067743)

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Record Information

Version

2.0

Created at

2022-04-28 12:35:45 UTC

Updated at

2022-04-28 12:35:46 UTC

NP-MRD ID

NP0067743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3alpha-Phenylacetoxytropane

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. 3alpha-Phenylacetoxytropane is found in Atropa baetica, Atropa belladonna L. , Brugmansia candida, Datura candida X candida , Datura stramonium , Erythroxylum dekindtii (Engl.)O.E.Schultz, Erythroxylum hypericifolium Lam. and Erythroxylum pervillei. Is possibly soluble (in water) and a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.2950    0.9425    1.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996    0.4508    0.8022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -0.9602    0.5650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1974   -1.0840   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842    0.0723   -1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162    0.9851   -0.5570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5830    0.8597   -0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9007   -0.2374   -0.1774 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3427   -0.4677   -0.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5655   -0.2136   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513    0.3008    0.9629 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.4896   -0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -0.0995    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010    1.1494   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801    1.4734    0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    0.5530    1.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6351   -0.6954    1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -1.0135    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802   -1.4219    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849    2.0508    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1967    0.8266    0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921    0.5440    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183   -1.5115    1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0447   -2.0347   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000   -1.0834   -0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3202   -0.2596   -2.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7780    0.6094   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3278    2.0307   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9860    1.7903   -0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    0.5932   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428    0.2202    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -1.5680   -1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713    0.0502   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721    1.8735   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0785    2.4744    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0553    0.7933    2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0360   -1.4344    2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070   -1.9968    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -2.0079   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -2.0644    0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 19  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6  2  1  0
 18 13  1  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  1
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  1
 19 39  1  0
 19 40  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv1652312151802592D          

 19 21  0  0  0  0            999 V2000
 9984.3638 9988.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.2007 9988.2932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8435 9987.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.5566 9988.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2723 9987.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.5566 9988.9097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1318 9988.0992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.6272 9987.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.9363 9988.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8023 9987.4342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.4498 9988.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.2783 9988.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1876 9989.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.4146 9988.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7001 9989.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9856 9988.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9855 9988.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7000 9987.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4146 9988.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7  3  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  5 17  1  0  0  0  0
 13  2  1  1  0  0  0
 10  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO2/c1-17-13-7-8-14(17)11-15(10-13)19-16(18)9-12-5-3-2-4-6-12/h2-6,13-15H,7-11H2,1H3/t13-,14+,15+

> <INCHI_KEY>
DCINQANYMBYYCH-FICVDOATSA-N

> <FORMULA>
C16H21NO2

> <MOLECULAR_WEIGHT>
259.349

> <EXACT_MASS>
259.15722892

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.963807179046853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.3090258949999987

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.385562742930313

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
74.46720000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl phenylacetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 15-DEC-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-DEC-18         0                                  
HETATM    1  C   UNK     0    8637.4798645.418   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8640.9088644.814   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0    8643.9758643.654   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8645.3068644.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8646.6428643.654   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8645.3068645.965   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8642.6468644.452   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8641.7048643.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8642.2818645.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8640.1648643.211   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8639.5068645.906   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8639.1868644.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8640.8848646.595   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8650.6418645.964   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8649.3078646.734   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8647.9738645.964   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8647.9738644.424   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8649.3078643.654   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8650.6418644.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1   13   10                                                  
CONECT    3    4    7                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4   17                                                       
CONECT    6    4                                                            
CONECT    7    8    9    3                                                  
CONECT    8    7   10                                                       
CONECT    9    7   13                                                       
CONECT   10    8   12    2                                                  
CONECT   11   12   13                                                       
CONECT   12   10   11                                                       
CONECT   13    9   11    2                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    5                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
3alpha-Phenylacetoxytropane	PhytoBank
3-Phenylacetoxytropane	PhytoBank
3α-Phenylacetoxytropane	PhytoBank

Chemical Formula

C₁₆H₂₁NO₂

Average Mass

259.3490 Da

Monoisotopic Mass

259.15723 Da

IUPAC Name

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenylacetate

Traditional Name

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl phenylacetate

CAS Registry Number

Not Available

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C16H21NO2/c1-17-13-7-8-14(17)11-15(10-13)19-16(18)9-12-5-3-2-4-6-12/h2-6,13-15H,7-11H2,1H3/t13-,14+,15+

InChI Key

DCINQANYMBYYCH-FICVDOATSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Atropa baetica	Plant	KNApSAcK
Atropa belladonna	Plant	KNApSAcK
Brugmansia x candida	LOTUS Database	35616633
Datura candida X candida	Plant	KNApSAcK
Datura stramonium	Plant	KNApSAcK
Erythroxylum dekindtii (Engl.)O.E.Schultz	Plant	KNApSAcK
Erythroxylum hypericifolium Lam.	Plant	KNApSAcK
Erythroxylum pervillei	Plant	KNApSAcK

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
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.79	ALOGPS
logP	2.31	ChemAxon
logS	-2.8	ALOGPS
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	74.47 m³·mol⁻¹	ChemAxon
Polarizability	28.96 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3alpha-Phenylacetoxytropane (NP0067743)

MOL for NP0067743 (3alpha-Phenylacetoxytropane)

3D MOL for NP0067743 (3alpha-Phenylacetoxytropane)

3D SDF for NP0067743 (3alpha-Phenylacetoxytropane)

3D-SDF for NP0067743 (3alpha-Phenylacetoxytropane)

PDB for NP0067743 (3alpha-Phenylacetoxytropane)

3D PDB for NP0067743 (3alpha-Phenylacetoxytropane)

SMILES for NP0067743 (3alpha-Phenylacetoxytropane)

INCHI for NP0067743 (3alpha-Phenylacetoxytropane)

Structure for NP0067743 (3alpha-Phenylacetoxytropane)

3D Structure for NP0067743 (3alpha-Phenylacetoxytropane)