NP-MRD: Showing NP-Card for Tropine (NP0331671)

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Record Information

Version

1.0

Created at

2023-06-03 04:00:31 UTC

Updated at

2024-04-19 09:50:40 UTC

NP-MRD ID

NP0331671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tropine

Description

It was first documented in 2009 (PMID: 19924779).

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol	ChEBI
1AlphaH,5alphah-tropan-3alpha-ol	ChEBI
3alpha-Tropanol	ChEBI
8-Methyl-8-azabicyclo[3.2.1]octan-3-ol	ChEBI
endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol	ChEBI
Tropanol	ChEBI
1AlphaH,5alphah-tropan-3a-ol	Generator
1AlphaH,5alphah-tropan-3α-ol	Generator
3a-Tropanol	Generator
3Α-tropanol	Generator
1αH,5αH-Tropan-3α-ol	PhytoBank
2,3-Dihydro-3alpha-hydroxy-8-methylnortropidine	PhytoBank
2,3-Dihydro-3α-hydroxy-8-methylnortropidine	PhytoBank
2,3-Dihydro-3alpha-hydroxytropidine	PhytoBank
2,3-Dihydro-3α-hydroxytropidine	PhytoBank
alpha-Tropine	PhytoBank
α-Tropine	PhytoBank

Chemical Formula

C₈H₁₅NO

Average Mass

141.2108 Da

Monoisotopic Mass

141.11536 Da

IUPAC Name

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

Traditional Name

pseudotropine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+

InChI Key

CYHOMWAPJJPNMW-JIGDXULJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 700 MHz, D2O, experimental)	jaewoo.choi@oregonstate.edu	Not Available	Not Available	2023-08-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-06-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-06-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-06-03	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-06-03	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-06-03	View Spectrum

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

Not Available

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
Cyclic alcohol
Pyrrolidine
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tropane alkaloid (CHEBI:15884 )

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	0.86	ALOGPS
logP	0.034	ChemAxon
logS	0.66	ALOGPS
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.59 m³·mol⁻¹	ChemAxon
Polarizability	16.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00002306

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tropine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15884

Good Scents ID

Not Available

References

General References

Molinie R, Kwiecien RA, Silvestre V, Robins RJ: Determination of nitrogen-15 isotope fractionation in tropine: evaluation of extraction protocols for isotope ratio measurement by isotope ratio mass spectrometry. Rapid Commun Mass Spectrom. 2009 Dec;23(24):4031-7. doi: 10.1002/rcm.4344. [PubMed:19924779 ]
Kwiecien RA, Molinie R, Paneth P, Silvestre V, Lebreton J, Robins RJ: Elucidation of the mechanism of N-demethylation catalyzed by cytochrome P450 monooxygenase is facilitated by exploiting nitrogen-15 heavy isotope effects. Arch Biochem Biophys. 2011 Jun 1;510(1):35-41. doi: 10.1016/j.abb.2011.03.007. Epub 2011 Mar 21. [PubMed:21420927 ]
Chiou WH, Chen GT, Kao CL, Gao YK: Syntheses of (-)-pelletierine and (-)-homopipecolic acid. Org Biomol Chem. 2012 Apr 7;10(13):2518-20. doi: 10.1039/c2ob06984a. Epub 2012 Feb 20. [PubMed:22349358 ]

Showing NP-Card for Tropine (NP0331671)

MOL for NP0331671 (Tropine)

3D MOL for NP0331671 (Tropine)

3D SDF for NP0331671 (Tropine)

3D-SDF for NP0331671 (Tropine)

PDB for NP0331671 (Tropine)

3D PDB for NP0331671 (Tropine)

SMILES for NP0331671 (Tropine)

INCHI for NP0331671 (Tropine)

Structure for NP0331671 (Tropine)

3D Structure for NP0331671 (Tropine)