TROPINONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H13NO
Molecular Weight	139.1949
Optical Activity	NONE
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QQXLDOJGLXJCSE-KNVOCYPGSA-N

InChI=1S/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3/t6-,7+

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: structural and functional aspects.	2001 Jan 30	11306095
Calystegines in Calystegia sepium derive from the tropane alkaloid pathway.	2001 Nov	11684185
Tropane alkaloid biosynthesis. A century old problem unresolved.	2001 Oct	11699882
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).	2002 Feb 1	11855731
Enantioselective synthesis of S-(+)-2beta-carboalkoxy-3alpha-[bis(4-fluorophenyl)methoxy]tropanes as novel probes for the dopamine transporter.	2002 May 6	11965364
Capturing enzyme structure prior to reaction initiation: tropinone reductase-II-substrate complexes.	2003 May 20	12741812
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.	2003 Sep	12885861
Chemistry and biology of calystegines.	2004 Apr	15042146
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.	2005 Apr 22	15781147
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.	2005 Feb	15642710
[Time-resolved X-ray crystallographic analysis on tropinone reductase-II using Laue diffraction method].	2005 Jul	16114850
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.	2006 Feb	16426652
Whole-genome analysis of the SHORT-ROOT developmental pathway in Arabidopsis.	2006 May	16640459
Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.	2008 Jul-Aug	18799813
An approach for synthesis of tropinone analogue N-substituted with triazine ring.	2008 Nov-Dec	19172859
Asymmetric synthesis of substituted tropinones using the intramolecular mannich cyclization reaction and acyclic N-sulfinyl beta-amino ketone ketals.	2009 Apr 2	19278245
Biogenetically inspired syntheses of alkaloid natural products.	2009 Nov	19847339
Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots.	2009 Oct 23	19751215
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.	2010 Apr 14	20480039
A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection.	2010 Aug 31	20807411
N-Methyl stereochemistry in tropinone: the conformational flexibility of the tropane motif.	2010 Jun 21	20405065
Coronatine-insensitive 1 (COI1) mediates transcriptional responses of Arabidopsis thaliana to external potassium supply.	2010 Mar	20339157
Whole genome wide expression profiles of Vitis amurensis grape responding to downy mildew by using Solexa sequencing technology.	2010 Oct 28	21029438

Patents

Name

Type

Language

TROPINONE

Common Name

English

8-AZABICYCLO(3.2.1)OCTAN-3-ONE, 8-METHYL-

Systematic Name

English

TROPINON

Common Name

English

TROPANONE

Common Name

English

(1R,5S)-8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-ONE

Systematic Name

English

N-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-ONE

Systematic Name

English

1.ALPHA.H,5.ALPHA.H-TROPAN-3-ONE

Systematic Name

English

NSC-118012

Code

English

8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-ONE

Systematic Name

English

3-TROPINONE

Common Name

English

3-TROPANONE

Common Name

English

Code System Code Type Description

WIKIPEDIA

Tropinone