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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:54:33 UTC

Update Date

2023-02-21 17:24:31 UTC

HMDB ID

HMDB0034975

Secondary Accession Numbers

HMDB34975

Metabolite Identification

Common Name

Piperitone

Description

Piperitone is found in ceylan cinnamon. Piperitone is a flavouring ingredient.Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (Wikipedia

Structure

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

COMPND    HMDB0034975
HETATM    1  C1  UNL     1       3.543  -0.145  -0.644  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.192   0.200  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.436   1.058  -0.771  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.125   1.367  -0.239  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.418   2.508  -0.413  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.607   0.352   0.519  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.668  -0.235  -0.401  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.599   0.885  -0.844  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.509  -1.263   0.308  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.234  -0.720   1.110  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.710  -0.428   1.096  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.710  -1.237  -0.697  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.302   0.368  -0.017  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.649   0.248  -1.678  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.783   1.532  -1.681  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.188   0.899   1.318  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.217  -0.671  -1.298  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.649   0.523  -0.963  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.658   1.685  -0.061  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.242   1.361  -1.781  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.956  -2.220   0.463  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.357  -1.508  -0.367  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.901  -0.858   1.251  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.099  -1.683   0.540  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.075  -0.867   2.166  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.990   0.222   1.973  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.268  -1.375   1.245  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5    5    6
CONECT    6    7   10   16
CONECT    7    8    9   17
CONECT    8   18   19   20
CONECT    9   21   22   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Carvomenthenone	ChEBI
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one	ChEBI
6-Isopropyl-3-methylcyclohex-2-enone	ChEBI
p-Menth-1-en-3-one	ChEBI
(+-)-Piperitone	HMDB
1-Methyl-4-isopropyl-1-cyclohexen-3-one	HMDB
3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one	HMDB
6-Isopropyl-3-methyl-2-cyclohexen-1-one	HMDB
DL-Piperitone	HMDB
FEMA 2910	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

piperitone

CAS Registry Number

89-81-6

SMILES

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

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3

InChI Key

YSTPAHQEHQSRJD-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
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

cyclic terpene ketone (CHEBI:48933 )
p-menthane monoterpenoid (CHEBI:48933 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034975)

Source

Endogenous

Endogenous (HMDB: HMDB0034975)

Plant

Plant (HMDB: HMDB0034975)

Animal

Animal (HMDB: HMDB0034975)

Exogenous

Food

Food (HMDB: HMDB0034975)

Tamarind (FooDB: FOOD00180)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Exogenous (HMDB: HMDB0034975)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034975)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034975)

Lipid metabolism pathway (HMDB: HMDB0034975)

Cellular process

Cell signaling (HMDB: HMDB0034975)

Biochemical process

Lipid transport (HMDB: HMDB0034975)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034975)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0034975)
Flavoring Agent (HMDB: HMDB0034975)

Agriculture

Pesticide

Herbicide (HMDB: HMDB0034975)

Pesticide (HMDB: HMDB0034975)

Fragrance (HMDB: HMDB0034975)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	233.00 to 235.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.85	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.47	ALOGPS
logP	3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.87	ChemAxon
pKa (Strongest Basic)	-4.6	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	1	ChemAxon
Refractivity	47.35 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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]+	138.216	31661259
DarkChem	[M-H]-	134.239	31661259
DeepCCS	[M+H]+	136.387	30932474
DeepCCS	[M-H]-	132.893	30932474
DeepCCS	[M-2H]-	170.1	30932474
DeepCCS	[M+Na]+	145.266	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.6	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.4	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	141.0	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.	6.04 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9978 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2119.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	520.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	301.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	131.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	567.9 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	664.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1151.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	430.0 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	1238.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	387.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	491.3 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	19.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperitone	CC(C)C1CCC(C)=CC1=O	1709.4	Standard polar	33892256
Piperitone	CC(C)C1CCC(C)=CC1=O	1203.2	Standard non polar	33892256
Piperitone	CC(C)C1CCC(C)=CC1=O	1231.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperitone,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC1	1391.6	Semi standard non polar	33892256
Piperitone,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC1	1333.6	Standard non polar	33892256
Piperitone,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	1626.1	Semi standard non polar	33892256
Piperitone,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	1540.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Piperitone EI-B (Non-derivatized)	splash10-01qi-9300000000-f92830f958dd7b7816c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Piperitone EI-B (Non-derivatized)	splash10-01qi-9300000000-f92830f958dd7b7816c0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperitone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9300000000-e3bec6231e4993e3d578	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperitone 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 - Piperitone 10V, Positive-QTOF	splash10-0udi-0900000000-0f2176d975b2f9bfe7fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 20V, Positive-QTOF	splash10-0w29-7900000000-bc07a247759df113c943	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 40V, Positive-QTOF	splash10-0a4l-9000000000-6e8d2587c3fab7a87b03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 10V, Negative-QTOF	splash10-0udi-0900000000-83fb585962f6ed48b378	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 20V, Negative-QTOF	splash10-0udi-0900000000-a2b215f78ea2edceb56c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 40V, Negative-QTOF	splash10-0a4u-8900000000-058070ac2054c97f9a30	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 10V, Positive-QTOF	splash10-0w29-1900000000-cf5ff8ec6a34a5b6435b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 20V, Positive-QTOF	splash10-0gb9-9200000000-ddaec970d54edc7cbf79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 40V, Positive-QTOF	splash10-00kf-9000000000-4c75828fad35f0eec374	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 20V, Negative-QTOF	splash10-0udi-0900000000-3f9a24ef7ca3da32a522	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone 40V, Negative-QTOF	splash10-014i-9400000000-172af5b361384699caf7	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

Extracellular
Membrane

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB013573

KNApSAcK ID

C00003054

Chemspider ID

6721

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piperitone

METLIN ID

Not Available

PubChem Compound

6987

PDB ID

Not Available

ChEBI ID

48933

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1049441

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 Piperitone (HMDB0034975)

MOL for HMDB0034975 (Piperitone)

3D MOL for HMDB0034975 (Piperitone)

3D SDF for HMDB0034975 (Piperitone)

3D-SDF for HMDB0034975 (Piperitone)

PDB for HMDB0034975 (Piperitone)

3D PDB for HMDB0034975 (Piperitone)

SMILES for HMDB0034975 (Piperitone)

INCHI for HMDB0034975 (Piperitone)

Structure for HMDB0034975 (Piperitone)

3D Structure for HMDB0034975 (Piperitone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra