Jump To Section:

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

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:09:27 UTC

Update Date

2023-02-21 17:25:03 UTC

HMDB ID

HMDB0036089

Secondary Accession Numbers

HMDB36089

Metabolite Identification

Common Name

(R)-Menthofuran

Description

(R)-Menthofuran belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on (R)-Menthofuran.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,9-Epoxy-p-mentha-3,8-diene	ChEBI
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran	ChEBI
4,5,6,7-Tetrahydro-3,6-dimethylcoumarone	ChEBI
(+)-3,9-Epoxy-P-mentha-3,8-diene	HMDB
(+)-Menthofuran	HMDB
(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran	HMDB
(R)-(+)-Menthofuran	HMDB
(R)-4,5,6,7-tetrahydro-3,6-Dimethylbenzofuran	HMDB
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran	HMDB
3,9-Epoxy-(+)-P-mentha-3,8-diene	HMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-(R)-benzofuran	HMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-benzofuran	HMDB
Menthofuran	HMDB
Menthofuran, (R)-isomer	MeSH, HMDB

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

IUPAC Name

3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran

Traditional Name

3,9-epoxy-p-mentha-3,8-diene

CAS Registry Number

17957-94-7

SMILES

CC1CCC2=C(C1)OC=C2C

InChI Identifier

InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

InChI Key

YGWKXXYGDYYFJU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Menthofuran monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:50542 )
monoterpenoid (CHEBI:50542 )
Menthane monoterpenoids (C09868 )
Iridoids (C09868 )
a monoterpenoid (CPD-4981 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0036089)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036089)

Source

Endogenous

Endogenous (HMDB: HMDB0036089)

Plant

Plant (HMDB: HMDB0036089)

Animal

Animal (HMDB: HMDB0036089)

Exogenous

Food

Food (HMDB: HMDB0036089)

Herb and spice

Herb

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036089)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036089)

Lipid metabolism pathway (HMDB: HMDB0036089)

Cellular process

Cell signaling (HMDB: HMDB0036089)

Biochemical process

Lipid transport (HMDB: HMDB0036089)

Role

Biological role

Industrial application

Agriculture

Pesticide

Nematicide (HMDB: HMDB0036089)

Pesticide (HMDB: HMDB0036089)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	86.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	80.00 to 82.00 °C. @ 13.00 mm Hg	The Good Scents Company Information System
Water Solubility	16.36 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.562 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.073 g/L	ALOGPS
logP	3.98	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.67 m³·mol⁻¹	ChemAxon
Polarizability	18.04 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]+	132.929	31661259
DarkChem	[M-H]-	128.732	31661259
DeepCCS	[M+H]+	134.78	30932474
DeepCCS	[M-H]-	131.692	30932474
DeepCCS	[M-2H]-	168.816	30932474
DeepCCS	[M+Na]+	143.917	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.1	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.4	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	136.9	32859911
AllCCS	[M+HCOO]-	138.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Menthofuran	CC1CCC2=C(C1)OC=C2C	1510.1	Standard polar	33892256
(R)-Menthofuran	CC1CCC2=C(C1)OC=C2C	1131.3	Standard non polar	33892256
(R)-Menthofuran	CC1CCC2=C(C1)OC=C2C	1163.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (R)-Menthofuran EI-B (Non-derivatized)	splash10-0a4i-4900000000-ad7d24da86fd955477a7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-Menthofuran EI-B (Non-derivatized)	splash10-0a4i-4900000000-ad7d24da86fd955477a7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Menthofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi9-1900000000-c7d34068fe20520e5e88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Menthofuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Menthofuran 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 - (R)-Menthofuran 10V, Positive-QTOF	splash10-0udi-0900000000-295d2c3abad7c8ff4f63	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOF	splash10-0udi-3900000000-5e060ac38ef1d423776f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOF	splash10-0gb9-9100000000-30417e50d66ad0fe9af6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Positive-QTOF	splash10-0udi-0900000000-295d2c3abad7c8ff4f63	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOF	splash10-0udi-3900000000-5e060ac38ef1d423776f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOF	splash10-0gb9-9100000000-30417e50d66ad0fe9af6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOF	splash10-0002-0900000000-881d258a03659e0f3930	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOF	splash10-0002-0900000000-01ff41b309657177e5e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOF	splash10-066r-3900000000-177076fd487978d174f1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOF	splash10-0002-0900000000-881d258a03659e0f3930	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOF	splash10-0002-0900000000-01ff41b309657177e5e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOF	splash10-066r-3900000000-177076fd487978d174f1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Positive-QTOF	splash10-0udi-1900000000-a36c450a85a702daacb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOF	splash10-0zfs-9800000000-283087fbd503dd386078	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOF	splash10-002f-9100000000-bb914f0c52d327a80b1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOF	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOF	splash10-0002-0900000000-8ae160b4249f862d1a00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOF	splash10-05ne-7900000000-12e4673f2e9f1e3c406d	2021-09-23	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

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

Menthofuran

METLIN ID

Not Available

PubChem Compound

329983

PDB ID

Not Available

ChEBI ID

50542

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1019781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Miyazawa M, Haigou R: Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. Xenobiotica. 2011 Dec;41(12):1056-62. doi: 10.3109/00498254.2011.596230. [PubMed:22054099 ]
Thomassen D, Slattery JT, Nelson SD: Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. J Pharmacol Exp Ther. 1988 Mar;244(3):825-9. [PubMed:3252034 ]
Yu S, Chen Y, Zhang L, Shan M, Tang Y, Ding A: Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times. Int J Mol Sci. 2011;12(10):6635-44. doi: 10.3390/ijms12106635. Epub 2011 Oct 10. [PubMed:22072908 ]
Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug Metab Dispos. 2003 Oct;31(10):1208-13. [PubMed:12975329 ]
Stephens ES, Walsh AA, Scott EE: Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. Drug Metab Dispos. 2012 Sep;40(9):1797-802. doi: 10.1124/dmd.112.045161. Epub 2012 Jun 13. [PubMed:22696418 ]
Miyazawa M, Marumoto S, Takahashi T, Nakahashi H, Haigou R, Nakanishi K: Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes. J Oleo Sci. 2011;60(3):127-32. [PubMed:21343660 ]
Khojasteh-Bakht SC, Nelson SD, Atkins WM: Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. Arch Biochem Biophys. 1999 Oct 1;370(1):59-65. [PubMed:10496977 ]
Haigou R, Miyazawa M: Metabolism of (+)-terpinen-4-ol by cytochrome P450 enzymes in human liver microsomes. J Oleo Sci. 2012;61(1):35-43. [PubMed:22188805 ]
Atsbaha Zebelo S, Bertea CM, Bossi S, Occhipinti A, Gnavi G, Maffei ME: Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L. PLoS One. 2011 Mar 9;6(3):e17195. doi: 10.1371/journal.pone.0017195. [PubMed:21408066 ]
Lange BM, Mahmoud SS, Wildung MR, Turner GW, Davis EM, Lange I, Baker RC, Boydston RA, Croteau RB: Improving peppermint essential oil yield and composition by metabolic engineering. Proc Natl Acad Sci U S A. 2011 Oct 11;108(41):16944-9. doi: 10.1073/pnas.1111558108. Epub 2011 Sep 30. [PubMed:21963983 ]
Khojasteh-Bakht SC, Koenigs LL, Peter RM, Trager WF, Nelson SD: (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos. 1998 Jul;26(7):701-4. [PubMed:9660853 ]
Khojasteh-Bakht SC, Chen W, Koenigs LL, Peter RM, Nelson SD: Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Drug Metab Dispos. 1999 May;27(5):574-80. [PubMed:10220485 ]
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 (R)-Menthofuran (HMDB0036089)

MOL for HMDB0036089 ((R)-Menthofuran)

3D MOL for HMDB0036089 ((R)-Menthofuran)

3D SDF for HMDB0036089 ((R)-Menthofuran)

3D-SDF for HMDB0036089 ((R)-Menthofuran)

PDB for HMDB0036089 ((R)-Menthofuran)

3D PDB for HMDB0036089 ((R)-Menthofuran)

SMILES for HMDB0036089 ((R)-Menthofuran)

INCHI for HMDB0036089 ((R)-Menthofuran)

Structure for HMDB0036089 ((R)-Menthofuran)

3D Structure for HMDB0036089 ((R)-Menthofuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra