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

Molecular Formula	C8H13NO
Molecular Weight	139.1949
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Whole genome wide expression profiles of Vitis amurensis grape responding to downy mildew by using Solexa sequencing technology.	2010-10-28	21029438
A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection.	2010-08-31	20807411
N-Methyl stereochemistry in tropinone: the conformational flexibility of the tropane motif.	2010-06-21	20405065
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.	2010-04-14	20480039
Coronatine-insensitive 1 (COI1) mediates transcriptional responses of Arabidopsis thaliana to external potassium supply.	2010-03	20339157
Biogenetically inspired syntheses of alkaloid natural products.	2009-11	19847339
Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots.	2009-10-23	19751215
Asymmetric synthesis of substituted tropinones using the intramolecular mannich cyclization reaction and acyclic N-sulfinyl beta-amino ketone ketals.	2009-04-02	19278245
An approach for synthesis of tropinone analogue N-substituted with triazine ring.	2009-01-29	19172859
Medium- and short-chain dehydrogenase/reductase gene and protein families : the SDR superfamily: functional and structural diversity within a family of metabolic and regulatory enzymes.	2008-12	19011750
Protein structure modeling indicates hexahistidine-tag interference with enzyme activity.	2008-07	18214963
The functional divergence of short-chain dehydrogenases involved in tropinone reduction.	2008-05	18221363
Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.	2008-02-03	18799813
Highly stereoselective [4 + 3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles: an approach to parvineostemonine.	2007-03-29	17335226
Calystegines in potatoes with genetically engineered carbohydrate metabolism.	2007	17431026
Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts.	2006-12	16845528
Images in cardiovascular medicine. A rare form of midventricular Tako-Tsubo after emotional stress followed up with magnetic resonance imaging.	2006-08-15	16908776
Whole-genome analysis of the SHORT-ROOT developmental pathway in Arabidopsis.	2006-05	16640459
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.	2006-02	16426652
[Time-resolved X-ray crystallographic analysis on tropinone reductase-II using Laue diffraction method].	2005-07	16114850
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.	2005-04-22	15781147
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.	2005-02	15642710
Chemistry and biology of calystegines.	2004-04	15042146
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.	2003-09	12885861
Capturing enzyme structure prior to reaction initiation: tropinone reductase-II-substrate complexes.	2003-05-20	12741812
Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone.	2003-05-15	12713836
Biosynthesis of calystegines: 15N NMR and kinetics of formation in root cultures of Calystegia sepium.	2003-02	12620344
Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives.	2002-11-29	12444645
One-pot synthesis of tropinone by tandem (domino) ene-type reactions of acetone silyl enol ethers.	2002-11-21	12510269
Stereoselective syntheses of the three isomers of ethylene glycol bis(tropane-3-carboxylate).	2002-07-26	12126447
Enantioselective synthesis of S-(+)-2beta-carboalkoxy-3alpha-[bis(4-fluorophenyl)methoxy]tropanes as novel probes for the dopamine transporter.	2002-05-06	11965364
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).	2002-02-01	11855731
Calystegines in Calystegia sepium derive from the tropane alkaloid pathway.	2001-11	11684185
Tropane alkaloid biosynthesis. A century old problem unresolved.	2001-10	11699882
Photochemical N-demethylation of alkaloids.	2001-02-26	11229743
17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: structural and functional aspects.	2001-01-30	11306095

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 13:56:01 GMT 2025` Edited by `admin` on `Wed Apr 02 13:56:01 GMT 2025`
Record UNII	2A8CC8KA5F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TROPINONE

Common Name

English

NSC-118012

Preferred 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

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