NP-MRD: Showing NP-Card for Fenchone (NP0044869)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:55 UTC

Updated at

2025-02-11 15:48:07 UTC

NP-MRD ID

NP0044869

Natural Product DOI

https://doi.org/10.57994/2765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fenchone

Description

Fenchone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, fenchone is an isoprenoid lipid molecule. Fenchone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Fenchone is a colorless oily liquid with a bitter, camphor, and cedar leaf taste. Fenchone occurs in fennels (https://Doi.Org/10.1111/J.2042-7158.1968.Tb09783.X), rosemaries, and star anises making fenchone a potential biomarker for the consumption of these foods. Fenchone was detected in the fresh bud of the cannabis plant (PMID: 8984153 ). Fenchone is used as a flavor in foods such as candy and baked goods and to add scents to soaps, detergents, perfumes and lotions. It also an insect repellent.

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
(-)-Fenchone	ChEBI
(1R)-(-)-Fenchone	ChEBI
(1R)-Fenchone	ChEBI
(1R,4S)-(-)-Fenchone	ChEBI
(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one	ChEBI
(R)-(-)-Fenchone	PhytoBank
(R)-Fenchone	PhytoBank
L-(-)-Fenchone	PhytoBank
l-Fenchone	PhytoBank
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one	PhytoBank
(±)-Fenchone	PhytoBank
1,3,3-Trimethyl-2-norbornanone	PhytoBank
1,3,3-Trimethylnorcamphor	PhytoBank
dl-Fenchone	PhytoBank

Chemical Formula

C₁₀H₁₆O

Average Mass

152.2370 Da

Monoisotopic Mass

152.12012 Da

IUPAC Name

(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

Traditional Name

fenchone, (+-)-

CAS Registry Number

7787-20-4

SMILES

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

InChI Identifier

InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

InChI Key

LHXDLQBQYFFVNW-OIBJUYFYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Alphinia galanga	-	KNApSAcK
Anethum foeniculum	Plant	KNApSAcK
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Blumea lacera	Plant	KNApSAcK
Cannabis sativa	NULL	Not Available
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cistus albidus	Plant	KNApSAcK
Crocus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Falcaria vulgaris	Plant	KNApSAcK
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Illicium verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lavandula stoechas	Plant	KNApSAcK
Lippia ukambensis	Plant	KNApSAcK
Nigella sativa L	Plant	KNApSAcK
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus halepensis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Plectranthus marrubioides	Plant	KNApSAcK
Prunella vulgaris	Plant	KNApSAcK
Quercus coccifera	Plant	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Strobilanthes ixiocephala	Plant	KNApSAcK
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tarchonanthus camphoratus	Plant	KNApSAcK
Tetradenia riparia	Plant	KNApSAcK
Thuja occidentalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Fenchane monoterpenoid
Bicyclic monoterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

fenchone (CHEBI:36612 )
Bicyclic monoterpenoids (LMPR0102120031 )

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	2.54	ALOGPS
logP	3.06	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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

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

82229

PDB ID

Not Available

ChEBI ID

36612

Good Scents ID

Not Available

References

General References

Aprotosoaie AC, Spac A, Cioanca O, Trifan A, Miron A, Hancianu M: The chemical composition of essential oils isolated from sweet fennel fruits available as herbal tea products. Rev Med Chir Soc Med Nat Iasi. 2013 Jul-Sep;117(3):819-24. [PubMed:24502057 ]

Showing NP-Card for Fenchone (NP0044869)

MOL for NP0044869 (Fenchone)

3D MOL for NP0044869 (Fenchone)

3D SDF for NP0044869 (Fenchone)

3D-SDF for NP0044869 (Fenchone)

PDB for NP0044869 (Fenchone)

3D PDB for NP0044869 (Fenchone)

SMILES for NP0044869 (Fenchone)

INCHI for NP0044869 (Fenchone)

Structure for NP0044869 (Fenchone)

3D Structure for NP0044869 (Fenchone)