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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:14:31 UTC

Update Date

2023-02-21 17:25:32 UTC

HMDB ID

HMDB0036999

Secondary Accession Numbers

HMDB36999

Metabolite Identification

Common Name

Piperitenone

Description

Piperitenone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, piperitenone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Piperitenone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one	HMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ci	HMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-one	HMDB
3-Terpinolenone	HMDB
6-Isopropylidene-3-methyl-2-cyclohexenone	HMDB
FEMA 3560	HMDB
Pulespenone	HMDB

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

IUPAC Name

3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

Traditional Name

piperitenone

CAS Registry Number

491-09-8

SMILES

CC(C)=C1CCC(C)=CC1=O

InChI Identifier

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3

InChI Key

HKZQJZIFODOLFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Quinomethane
O-quinomethane
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthadien-3-one (CHEBI:17304 )
Menthane monoterpenoids (C01951 )
Cyclic monoterpenes (C01951 )
Menthane monoterpenoids (LMPR0102090056 )
a small molecule (CPD-278 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036999)

Source

Endogenous

Endogenous (HMDB: HMDB0036999)

Plant

Plant (HMDB: HMDB0036999)

Animal

Animal (HMDB: HMDB0036999)

Exogenous

Food

Food (HMDB: HMDB0036999)

Herb and spice

Herb

Herbs and Spices (FooDB: FOOD00866)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0036999)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036999)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036999)

Lipid metabolism pathway (HMDB: HMDB0036999)

Cellular process

Cell signaling (HMDB: HMDB0036999)

Biochemical process

Lipid transport (HMDB: HMDB0036999)

Role

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	106.00 to 107.00 °C. @ 10.00 mm Hg	The Good Scents Company Information System
Water Solubility	164.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.766 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.05 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.81	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	18.6	ChemAxon
pKa (Strongest Basic)	-3.9	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	47.96 m³·mol⁻¹	ChemAxon
Polarizability	17.77 Å³	ChemAxon
Number of Rings	1	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]+	136.013	31661259
DarkChem	[M-H]-	132.764	31661259
DeepCCS	[M+H]+	134.384	30932474
DeepCCS	[M-H]-	130.626	30932474
DeepCCS	[M-2H]-	168.034	30932474
DeepCCS	[M+Na]+	143.37	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	126.1	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	137.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.66 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3182 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2154.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	541.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	336.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	543.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	688.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1211.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	442.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1227.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	552.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	24.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperitenone	CC(C)=C1CCC(C)=CC1=O	1843.2	Standard polar	33892256
Piperitenone	CC(C)=C1CCC(C)=CC1=O	1290.2	Standard non polar	33892256
Piperitenone	CC(C)=C1CCC(C)=CC1=O	1314.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piperitenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7c-8900000000-f5b1034f0ad5612f0f1e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperitenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 10V, Positive-QTOF	splash10-0udi-0900000000-c4031753132982c55fab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 20V, Positive-QTOF	splash10-0pb9-7900000000-9a0d9372d2684846d39b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 40V, Positive-QTOF	splash10-0gb9-9100000000-82fba962be7e9686c517	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 10V, Negative-QTOF	splash10-0002-0900000000-b7c0004066c195aa4089	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 20V, Negative-QTOF	splash10-0002-0900000000-49abeb92134d82dda90e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 40V, Negative-QTOF	splash10-053s-2900000000-fba0f16e8603dd89ee04	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 10V, Positive-QTOF	splash10-0udi-1900000000-7be39bdd81d4a83f56ee	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 20V, Positive-QTOF	splash10-00kf-9300000000-b6529814b27363caeb9a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 40V, Positive-QTOF	splash10-0006-9000000000-51ccd861c84166dd6b2c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 10V, Negative-QTOF	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 20V, Negative-QTOF	splash10-0002-0900000000-cfb5c45cee930f53ee1b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitenone 40V, Negative-QTOF	splash10-0159-9100000000-afc2d70a9cbeb08c1230	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
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

Not Available

METLIN ID

Not Available

PubChem Compound

381152

PDB ID

Not Available

ChEBI ID

17304

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1031141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Romagnoli C, Bruni R, Andreotti E, Rai MK, Vicentini CB, Mares D: Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L. Protoplasma. 2005 Apr;225(1-2):57-65. Epub 2005 May 4. [PubMed:15868213 ]
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 Piperitenone (HMDB0036999)

MOL for HMDB0036999 (Piperitenone)

3D MOL for HMDB0036999 (Piperitenone)

3D SDF for HMDB0036999 (Piperitenone)

3D-SDF for HMDB0036999 (Piperitenone)

PDB for HMDB0036999 (Piperitenone)

3D PDB for HMDB0036999 (Piperitenone)

SMILES for HMDB0036999 (Piperitenone)

INCHI for HMDB0036999 (Piperitenone)

Structure for HMDB0036999 (Piperitenone)

3D Structure for HMDB0036999 (Piperitenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra