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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:11 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036084

Secondary Accession Numbers

HMDB36084

Metabolite Identification

Common Name

Isomintlactone

Description

Isomintlactone belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Isomintlactone is found, on average, in the highest concentration within peppermints (Mentha X piperita). Isomintlactone has also been detected, but not quantified in, herbs and spices. This could make isomintlactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isomintlactone.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.925   0.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.385   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.461   2.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.923   1.539   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.925  -3.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.847  -2.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.307  -2.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.923  -1.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.615  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.923  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.155  -0.923   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.923   3.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3   10                                                       
CONECT    5    6                                                            
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    6   10                                                       
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Isomintlactone	HMDB
5,6,7,7a-tetrahydro-3,6-Dimethyl-(4H)-benzofuran-2-one	HMDB
5,6,7,7a-tetrahydro-3,6-Dimethyl-2(4H)-benzofuranone	HMDB
Menthalactone	HMDB
Mintlactone	HMDB, MeSH
Isomintlactone	MeSH

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

3,6-dimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

3,6-dimethyl-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one

CAS Registry Number

75684-66-1

SMILES

CC1CCC2=C(C)C(=O)OC2C1

InChI Identifier

InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3

InChI Key

VUVQBYIJRDUVHT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036084)

Source

Exogenous

Food

Food (HMDB: HMDB0036084)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036084)

Endogenous

Plant

Plant (HMDB: HMDB0036084)

Endogenous (HMDB: HMDB0036084)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036084)

Role

Biological role

Energy source (HMDB: HMDB0036084)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036084)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036084)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	77 - 79 °C	Not Available
Boiling Point	303.73 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1421 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.811 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.38	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	15.32	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.18 m³·mol⁻¹	ChemAxon
Polarizability	18.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	139.565	31661259
DarkChem	[M-H]-	134.077	31661259
DeepCCS	[M+H]+	138.27	30932474
DeepCCS	[M-H]-	135.043	30932474
DeepCCS	[M-2H]-	172.043	30932474
DeepCCS	[M+Na]+	147.524	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	131.8	32859911
AllCCS	[M+NH4]+	140.4	32859911
AllCCS	[M+Na]+	141.6	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	141.4	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.	6.2 minutes	32390414
Predicted by Siyang on May 30, 2022	16.2874 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2238.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	553.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	352.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	631.9 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	779.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	147.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1306.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	473.9 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	1446.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	554.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	546.1 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	63.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isomintlactone	CC1CCC2=C(C)C(=O)OC2C1	2358.0	Standard polar	33892256
Isomintlactone	CC1CCC2=C(C)C(=O)OC2C1	1398.8	Standard non polar	33892256
Isomintlactone	CC1CCC2=C(C)C(=O)OC2C1	1531.8	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 - Isomintlactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-4900000000-032591e918bf82ddf4c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomintlactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isomintlactone 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 - Isomintlactone 10V, Positive-QTOF	splash10-014i-5900000000-956f776e0729ea41a132	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 20V, Positive-QTOF	splash10-0005-9200000000-d7722a5f0cc17cb57624	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 40V, Positive-QTOF	splash10-0ldl-9100000000-20532fe312e467c237c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 10V, Negative-QTOF	splash10-014i-0900000000-8da45013e02f856f545f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 20V, Negative-QTOF	splash10-01b9-0900000000-b1030fda67b5c4b51280	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 40V, Negative-QTOF	splash10-01bc-6900000000-0502b635422f3f320e6b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 10V, Positive-QTOF	splash10-014i-0900000000-ddb0b4ad317a92ec611b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 20V, Positive-QTOF	splash10-014i-1900000000-a7fbb5eb50805dd35767	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 40V, Positive-QTOF	splash10-0006-9100000000-a0bcf66e820d21284568	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 20V, Negative-QTOF	splash10-014i-0900000000-75010ebf4b82319ad910	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isomintlactone 40V, Negative-QTOF	splash10-01dm-6900000000-40582a9e2b529932f4f8	2021-09-23	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

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

FDB014920

KNApSAcK ID

C00010950

Chemspider ID

85151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94349

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1596001

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isomintlactone (HMDB0036084)

MOL for HMDB0036084 (Isomintlactone)

3D MOL for HMDB0036084 (Isomintlactone)

3D SDF for HMDB0036084 (Isomintlactone)

3D-SDF for HMDB0036084 (Isomintlactone)

PDB for HMDB0036084 (Isomintlactone)

3D PDB for HMDB0036084 (Isomintlactone)

SMILES for HMDB0036084 (Isomintlactone)

INCHI for HMDB0036084 (Isomintlactone)

Structure for HMDB0036084 (Isomintlactone)

3D Structure for HMDB0036084 (Isomintlactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra