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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:55:16 UTC

Update Date

2023-02-21 17:24:31 UTC

HMDB ID

HMDB0034985

Secondary Accession Numbers

HMDB34985

Metabolite 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 considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (+)-Fenchone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0034985
HETATM    1  C1  UNL     1      -2.382  -0.001   1.181  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.230   0.093   0.284  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.544   0.570  -1.121  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.244   0.209  -1.837  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.527  -0.678  -0.906  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.626  -1.277  -0.078  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.154   0.148   0.199  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.185   1.098  -0.264  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.708  -0.798   1.238  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.051   0.803   0.799  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.021   1.744   1.564  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.271  -0.327   0.645  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.534   0.963   1.704  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.169  -0.786   1.961  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.773   1.630  -1.174  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.332  -0.091  -1.527  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.453  -0.281  -2.811  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.255   1.164  -2.069  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.162  -1.414  -1.352  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.320  -1.842  -0.701  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.259  -1.790   0.812  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.194   0.610  -0.118  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.177   1.991   0.397  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.149   1.358  -1.338  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.049  -0.894   2.117  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.922  -1.802   0.806  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.683  -0.398   1.588  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    6   10
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    7   19
CONECT    6   20   21
CONECT    7    8    9   10
CONECT    8   22   23   24
CONECT    9   25   26   27
CONECT   10   11   11
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,3-Trimethyl-2-norbornanone	ChEBI
1,3,3-Trimethyl-2-norcamphanone	ChEBI
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one	ChEBI
(1R,4S)-(+)-Fenchone	HMDB
(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]Heptan-2-one	HMDB
(1R,4S)-Fenchan-2-one	HMDB
(1R,4S)-Fenchone	HMDB
L-alpha-Fenchone	HMDB
L-Fenchone	HMDB
Fenchone, (1S)-isomer	MeSH, HMDB
Fenchone, (+-)-isomer	MeSH, HMDB
Fenchone, (1R)-isomer	MeSH, HMDB
(+)-Fenchone	KEGG

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

Traditional Name

fenchone

CAS Registry Number

7787-20-4

SMILES

CC1(C)C2CCC(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

InChI Key

LHXDLQBQYFFVNW-UHFFFAOYSA-N

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

carbobicyclic compound (CHEBI:4999 )
cyclic terpene ketone (CHEBI:4999 )
fenchane monoterpenoid (CHEBI:4999 )
Bicyclic monoterpenoids (C11387 )
Cyclic monoterpenes (C11387 )
Bicyclic monoterpenoids (LMPR0102120016 )
a small molecule (CPD-13994 )

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034985)
Membrane (HMDB: HMDB0034985)

Fennel (FooDB: FOOD00082)
Rosemary (FooDB: FOOD00159)

Spice

Star anise (FooDB: FOOD00090)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	5-6 °C	Not Available
Boiling Point	192.00 to 194.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	73.14 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.52	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.311	31661259
DarkChem	[M-H]-	130.605	31661259
DeepCCS	[M+H]+	137.195	30932474
DeepCCS	[M-H]-	133.368	30932474
DeepCCS	[M-2H]-	170.865	30932474
DeepCCS	[M+Na]+	146.403	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.4	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	138.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Fenchone	CC1(C)C2CCC(C)(C2)C1=O	1398.7	Standard polar	33892256
(+)-Fenchone	CC1(C)C2CCC(C)(C2)C1=O	1067.5	Standard non polar	33892256
(+)-Fenchone	CC1(C)C2CCC(C)(C2)C1=O	1071.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)	splash10-001i-9000000000-39548fbec25228381f9b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)	splash10-001i-9000000000-a6f20ad638918f01e975	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)	splash10-001i-9000000000-39548fbec25228381f9b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)	splash10-001i-9000000000-a6f20ad638918f01e975	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (+)-Fenchone GC-EI-Q (Non-derivatized)	splash10-00lr-9000000000-6be6cc8fad0feab50dc4	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Fenchone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0043-9400000000-8a489af79633badeca62	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Fenchone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00lr-9000000000-0490bda5c76f7c0af3bd	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Positive-QTOF	splash10-0udi-0900000000-24a8ed13cef6845f9bec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Positive-QTOF	splash10-0udi-5900000000-48ac2ef18d27307d28a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Positive-QTOF	splash10-00or-9200000000-a262db5efd11c7793ea7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Negative-QTOF	splash10-0udi-0900000000-611d1944cb83d52bd473	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Negative-QTOF	splash10-0udi-0900000000-aa8c9e54bea95cd3d999	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Negative-QTOF	splash10-01c9-5900000000-7356fe255f32eabff21c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Negative-QTOF	splash10-0udi-0900000000-2a5636c44361fc473306	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Positive-QTOF	splash10-0udi-2900000000-620886e230bbabe8a4ef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Positive-QTOF	splash10-0ue9-5900000000-b24f702346175a6b0100	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Positive-QTOF	splash10-0043-9200000000-42f567566720679e24e5	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenchone

METLIN ID

Not Available

PubChem Compound

14525

PDB ID

Not Available

ChEBI ID

4999

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1044072

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (+)-Fenchone (HMDB0034985)

MOL for HMDB0034985 ((+)-Fenchone)

3D MOL for HMDB0034985 ((+)-Fenchone)

3D SDF for HMDB0034985 ((+)-Fenchone)

3D-SDF for HMDB0034985 ((+)-Fenchone)

PDB for HMDB0034985 ((+)-Fenchone)

3D PDB for HMDB0034985 ((+)-Fenchone)

SMILES for HMDB0034985 ((+)-Fenchone)

INCHI for HMDB0034985 ((+)-Fenchone)

Structure for HMDB0034985 ((+)-Fenchone)

3D Structure for HMDB0034985 ((+)-Fenchone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra