Jump To Section:

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 20:36:49 UTC

Update Date

2023-02-21 17:24:50 UTC

HMDB ID

HMDB0035604

Secondary Accession Numbers

HMDB0061794
HMDB35604
HMDB61794

Metabolite Identification

Common Name

Pulegone

Description

Pulegone 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. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ).

Structure

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

COMPND    HMDB0035604
HETATM    1  C1  UNL     1       2.632  -1.425  -0.707  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.079  -0.086  -0.365  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.982   1.054  -0.447  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.805  -0.024  -0.010  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.049  -1.256   0.045  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.304  -0.928   0.840  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.054   0.139   0.071  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.440   0.282   0.649  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.311   1.445   0.112  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.155   1.232   0.347  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.877   2.137   0.865  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.807  -2.152  -0.962  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.156  -1.859   0.171  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.294  -1.405  -1.581  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.881   0.808  -1.022  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.519   1.995  -0.784  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.343   1.267   0.603  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.471  -2.074   0.611  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.308  -1.589  -0.961  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.901  -1.840   0.918  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.031  -0.529   1.835  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.102  -0.186  -0.994  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.344   0.342   1.747  1.00  0.00           H  
HETATM   24  H13 UNL     1      -4.041  -0.614   0.359  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.905   1.219   0.289  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.710   2.017   0.997  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.500   2.031  -0.789  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   10
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   10   26   27
CONECT   10   11   11
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-(R)-Pulegone	ChEBI
(1R)-(+)-p-Menth-4(8)-en-3-one	ChEBI
(5R)-2-Isopropylidene-5-methylcyclohexanone	ChEBI
(R)-Pulegone	ChEBI
D-Pulegone	ChEBI
(+)-Pulegone	Kegg
Pulegone, (R)-isomer	HMDB
(R)-(+)-p-Menth-4(8)-en-3-one	HMDB
(R)-p-Menth-4(8)-en-3-one	HMDB
p-Menth-4(8)-en-3-one	HMDB
(R)-5-Methyl-2-(1-methylethylidene)cyclohexanone	HMDB
(R)-(+)-Pulegone	HMDB
(1R)-Pulegone	HMDB
L-Pulegone	HMDB
NSC 15334	HMDB
Pulegon	HMDB
FEMA 2963	HMDB
(+)-4(8)-Para-menthen-3-one	HMDB
5-Methyl-2-(1-methylethylidene)cyclohexanone	HMDB
Pulegone	ChEBI
(5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone	PhytoBank

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one

Traditional Name

(+)-pulegone

CAS Registry Number

89-82-7

SMILES

C[C@@H]1CCC(=C(C)C)C(=O)C1

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

InChI Key

NZGWDASTMWDZIW-MRVPVSSYSA-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
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-menth-4(8)-en-3-one (CHEBI:35596 )
Menthane monoterpenoids (C09893 )
Cyclic monoterpenes (C09893 )
Menthane monoterpenoids (LMPR0102090025 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Extracellular (HMDB: HMDB0035604)
Membrane (HMDB: HMDB0035604)

Source

Exogenous

Exogenous (HMDB: HMDB0035604)

Food

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)
Highbush blueberry (FooDB: FOOD00191)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herb

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0035604)

Not Available

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0035604)
EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0035604)

Enzyme inhibitor

Acetylcholinesterase inhibitor (HMDB: HMDB0035604)

Industrial application

Agriculture

Pesticide

Pesticide (HMDB: HMDB0035604)

Antipyretic (HMDB: HMDB0035604)
Fragrance (HMDB: HMDB0035604)

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0035604)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0035604)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (HMDB: HMDB0035604)

Indirect biological role

Metabotoxin

Neurotoxin (HMDB: HMDB0035604)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	220.00 to 222.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	173.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.08	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.29 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.86	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-4.4	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	47.13 m³·mol⁻¹	ChemAxon
Polarizability	18.33 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]+	134.007	31661259
DarkChem	[M-H]-	131.777	31661259
DeepCCS	[M+H]+	141.242	30932474
DeepCCS	[M-H]-	138.821	30932474
DeepCCS	[M-2H]-	174.208	30932474
DeepCCS	[M+Na]+	149.211	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.4	32859911
AllCCS	[M+Na]+	137.6	32859911
AllCCS	[M-H]-	137.3	32859911
AllCCS	[M+Na-2H]-	138.8	32859911
AllCCS	[M+HCOO]-	140.6	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	16.024 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2201.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	573.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	344.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	604.5 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	718.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1268.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	453.0 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	1342.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	537.9 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	22.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pulegone	C[C@@H]1CCC(=C(C)C)C(=O)C1	1676.2	Standard polar	33892256
Pulegone	C[C@@H]1CCC(=C(C)C)C(=O)C1	1242.7	Standard non polar	33892256
Pulegone	C[C@@H]1CCC(=C(C)C)C(=O)C1	1239.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pulegone,1TMS,isomer #1	CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C	1410.3	Semi standard non polar	33892256
Pulegone,1TMS,isomer #1	CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C	1389.0	Standard non polar	33892256
Pulegone,1TBDMS,isomer #1	CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C	1620.2	Semi standard non polar	33892256
Pulegone,1TBDMS,isomer #1	CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C	1551.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Pulegone EI-B (Non-derivatized)	splash10-0f89-9200000000-103da19d7e73140f53a7	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pulegone GC-EI-Q (Non-derivatized)	splash10-0fsi-9300000000-5c40f6bc1c5dd5e64dc8	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btm-9600000000-72752a4904dbe00f2b4a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kur-9400000000-182826a9f81c661c7496	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 - Pulegone 10V, Positive-QTOF	splash10-0udi-0900000000-50f4b6a38ec680e83d0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 20V, Positive-QTOF	splash10-114i-6900000000-04a7ff4ee15b9b1c8161	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 40V, Positive-QTOF	splash10-0ldi-9100000000-2aee3b73ef815011023f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 10V, Negative-QTOF	splash10-0udi-0900000000-cd90c558f842f253efd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 20V, Negative-QTOF	splash10-0udi-0900000000-011197e33d9b4420c257	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 40V, Negative-QTOF	splash10-0a4u-6900000000-723bf6d0a35d2e10aafd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 10V, Positive-QTOF	splash10-0ik9-2900000000-7f3925a428ada570a2f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 20V, Positive-QTOF	splash10-00l6-9300000000-2fd8486379bd720b7b38	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 40V, Positive-QTOF	splash10-0006-9000000000-441dfa2e182dd78429bc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 20V, Negative-QTOF	splash10-0udi-0900000000-9fc5f57a10d95a4f369b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pulegone 40V, Negative-QTOF	splash10-014i-5900000000-7ce0df14de5e9c637a48	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Extracellular
Membrane

Biospecimen Locations

Saliva

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

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

Pulegone

METLIN ID

Not Available

PubChem Compound

442495

PDB ID

Not Available

ChEBI ID

35596

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Madyastha KM, Gaikwad NW: Metabolic fate of S-(-)-pulegone in rat. Xenobiotica. 1998 Aug;28(8):723-34. [PubMed:9741951 ]
Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-pulegone in F344 rats. Drug Metab Dispos. 2001 Dec;29(12):1567-77. [PubMed:11717176 ]
Yang JP, Bao BH, Zhang L, Ding AW: [Quantitative analysis of pulegone in Herba Schizonepetae]. Zhongguo Zhong Yao Za Zhi. 2005 May;30(9):669-70. [PubMed:16075729 ]
Dancewicz K, Gabrys B, Dams I, Wawrzenczyk C: Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding. J Chem Ecol. 2008 Apr;34(4):530-8. doi: 10.1007/s10886-008-9448-9. Epub 2008 Mar 14. [PubMed:18340487 ]
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 ]
Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
(). 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.
Wikipedia [Link]
Wikipedia [Link]
UniProt Q6WAU0 : (+)-pulegone reductase [Link]
Robert Carson, 'Cosmetic skin care compositions containing pulegone.' U.S. Patent US20020006423, issued January 17, 2002. [Link]

Showing metabocard for Pulegone (HMDB0035604)

MOL for HMDB0035604 (Pulegone)

3D MOL for HMDB0035604 (Pulegone)

3D SDF for HMDB0035604 (Pulegone)

3D-SDF for HMDB0035604 (Pulegone)

PDB for HMDB0035604 (Pulegone)

3D PDB for HMDB0035604 (Pulegone)

SMILES for HMDB0035604 (Pulegone)

INCHI for HMDB0035604 (Pulegone)

Structure for HMDB0035604 (Pulegone)

3D Structure for HMDB0035604 (Pulegone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra