NP-MRD: Showing NP-Card for 3beta-Acetoxytropane (NP0067744)

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Record Information

Version

2.0

Created at

2022-04-28 12:35:47 UTC

Updated at

2022-04-28 12:35:48 UTC

NP-MRD ID

NP0067744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-Acetoxytropane

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. 3beta-Acetoxytropane is found in Anthotroche myoporoides, Brugmansia suaveolens, Brugmansia candida, Bruguiera exaristata, Datura candida X candida , Datura discolor, Datura innoxia Mill , Datura inoxia, Datura metel L.var.fastuga , Datura sanguinea Ruiz.et Pav., Datura wrightii Regel, Hyoscyamus albus L. , Hyoscyamus boveanus, Hyoscyamus desertorum, Hyoscyamus muticus , Hyoscyamus pusillus L., Physalis peruviana and Physalis peruviana L. . 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

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.6604   -0.1274    0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.1388   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290   -0.2211   -1.5721 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1746   -0.0571    0.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -0.0633   -0.1748 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1632   -1.2958    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -1.0903    0.1144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7041   -0.5104   -1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.9538   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2574    1.1331    0.3933 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2089    1.2173    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6648   -0.0573    1.1016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750   -0.1184    1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669    0.4295   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929   -1.1525    0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6329    0.4018    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513   -0.1432   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -1.4133    1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -2.1696   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -2.0067    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523   -0.9256   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -0.5925   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831    1.2530   -0.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4187    1.6088   -1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    2.0526    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891    1.6865    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952    1.9407   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6191   -0.3698    0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2888   -0.9881    1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    0.7642    1.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  5  1  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 10 12  1  0
  6  7  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
  7 20  1  1
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  1
 11 26  1  0
 11 27  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
M  END

HEADER    PROTEIN                                 11-DEC-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-DEC-18         0                                  
HETATM    1  C   UNK     0    8660.0748668.018   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8663.5038667.414   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8665.2418667.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.2998665.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.8768668.548   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.7598665.810   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.1018668.506   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.7818667.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.4788669.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0798667.502   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8666.7458666.732   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8668.0798669.042   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8669.4138666.732   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    9    6                                                  
CONECT    3    4    5   11                                                  
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    8    2                                                  
CONECT    7    8    9                                                       
CONECT    8    6    7                                                       
CONECT    9    5    7    2                                                  
CONECT   10   12   13   11                                                  
CONECT   11   10    3                                                       
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
3beta-Acetoxytropane	PhytoBank
O-Acetylpseudotropine	PhytoBank

Chemical Formula

C₁₀H₁₇NO₂

Average Mass

183.2510 Da

Monoisotopic Mass

183.12593 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H17NO2/c1-7(12)13-10-5-8-3-4-9(6-10)11(8)2/h8-10H,3-6H2,1-2H3/t8-,9+,10-

InChI Key

MDIDMOWWLBGYPG-ILWJIGKKSA-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
Anthotroche myoporoides	LOTUS Database	35616633
Brugmansia suaveolens	LOTUS Database	35616633
Brugmansia x candida	LOTUS Database	35616633
Bruguiera exaristata	LOTUS Database	35616633
Datura candida X candida	Plant	KNApSAcK
Datura discolor	LOTUS Database	35616633
Datura innoxia Mill	Plant	KNApSAcK
Datura inoxia	LOTUS Database	35616633
Datura metel L.var.fastuga	Plant	KNApSAcK
Datura sanguinea Ruiz.et Pav.	Plant	KNApSAcK
Datura wrightii	Plant	KNApSAcK
Hyoscyamus albus	Plant	KNApSAcK
Hyoscyamus boveanus	Plant	KNApSAcK
Hyoscyamus desertorum	Plant	KNApSAcK
Hyoscyamus muticus	Plant	KNApSAcK
Hyoscyamus pusillus	Plant	KNApSAcK
Physalis peruviana	LOTUS Database	35616633
Physalis peruviana L.	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
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
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	1.18	ALOGPS
logP	0.47	ChemAxon
logS	-0.18	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	2	ChemAxon
Refractivity	49.75 m³·mol⁻¹	ChemAxon
Polarizability	20.28 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

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 3beta-Acetoxytropane (NP0067744)

MOL for NP0067744 (3beta-Acetoxytropane)

3D MOL for NP0067744 (3beta-Acetoxytropane)

3D SDF for NP0067744 (3beta-Acetoxytropane)

3D-SDF for NP0067744 (3beta-Acetoxytropane)

PDB for NP0067744 (3beta-Acetoxytropane)

3D PDB for NP0067744 (3beta-Acetoxytropane)

SMILES for NP0067744 (3beta-Acetoxytropane)

INCHI for NP0067744 (3beta-Acetoxytropane)

Structure for NP0067744 (3beta-Acetoxytropane)

3D Structure for NP0067744 (3beta-Acetoxytropane)