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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:10:38 UTC

Update Date

2021-09-23 16:10:38 UTC

HMDB ID

HMDB0302232

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran

Description

3,6-dimethyl-2,3,4,5,8,9-hexahydrobenzofuran, also known as anethofuran, is a member of the class of compounds known as benzofurans. Benzofurans 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. 3,6-dimethyl-2,3,4,5,8,9-hexahydrobenzofuran is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3,6-dimethyl-2,3,4,5,8,9-hexahydrobenzofuran can be found in dill, which makes 3,6-dimethyl-2,3,4,5,8,9-hexahydrobenzofuran a potential biomarker for the consumption of this food product. 3,6-dimethyl-2,3,4,5,8,9-hexahydrobenzofuran may be a unique S.cerevisiae (yeast) metabolite.

Structure

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

COMPND    HMDB0302232
HETATM    1  C1  UNL     1       3.445  -0.379   0.418  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.077  -0.188  -0.136  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.240  -1.192  -0.340  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.121  -1.020  -0.889  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.929  -2.013  -0.380  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.847  -1.470   0.463  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.731   0.015   0.466  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.031   0.723   0.168  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.726   0.297  -0.651  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.162   1.392  -0.204  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.625   1.173  -0.474  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.904  -1.325   0.066  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.421  -0.443   1.543  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.101   0.443   0.073  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.618  -2.195  -0.074  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.039  -1.227  -1.998  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.904  -1.812   0.270  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.627  -1.863   1.499  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.371   0.394   1.440  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.679   0.635   1.043  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.777   1.803   0.015  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.498   0.387  -0.781  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.292   0.606  -1.579  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.033   1.611   0.868  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.119   2.336  -0.739  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.181   1.888   0.167  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.885   1.423  -1.518  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5    9   16
CONECT    5    6
CONECT    6    7   17   18
CONECT    7    8    9   19
CONECT    8   20   21   22
CONECT    9   10   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6-Dimethyl-2,3,3a,4,5,7a-hexahydrobenzofuran	MeSH
Anethofuran	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1COC2C=C(C)CCC12

InChI Identifier

InChI=1S/C10H16O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h5,8-10H,3-4,6H2,1-2H3

InChI Key

KBPPPUZMFQKLNP-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
Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302232)

Food

Herb and spice

Herb

Dill (FooDB: FOOD00013)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.21	ALOGPS
logP	2.22	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.48 m³·mol⁻¹	ChemAxon
Polarizability	18.05 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
AllCCS	[M+H]+	132.403	32859911
AllCCS	[M+H-H2O]+	127.778	32859911
AllCCS	[M+Na]+	137.964	32859911
AllCCS	[M+NH4]+	136.718	32859911
AllCCS	[M-H]-	138.454	32859911
AllCCS	[M+Na-2H]-	139.604	32859911
AllCCS	[M+HCOO]-	140.942	32859911
DeepCCS	[M-2H]-	172.331	30932474
DeepCCS	[M+Na]+	147.713	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9800000000-64759402bfd048e4c873	2016-09-22	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 - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 10V, Positive-QTOF	splash10-0udi-0900000000-f5078e03ef1ed661e2e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 20V, Positive-QTOF	splash10-0udi-4900000000-1608dc93ed9d542dd429	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 40V, Positive-QTOF	splash10-0uxr-9100000000-ebdcebf70a5096d91479	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 10V, Negative-QTOF	splash10-0udi-0900000000-0ebc6168c5822135a3e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 20V, Negative-QTOF	splash10-0udi-1900000000-bb0b2ea30cc835a7ea1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 40V, Negative-QTOF	splash10-0avi-6900000000-e059117877b55de365aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 10V, Positive-QTOF	splash10-0udi-1900000000-6b5cb4f56d515685fe91	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 20V, Positive-QTOF	splash10-0zfv-9500000000-00eb3971593f2f1716ac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 40V, Positive-QTOF	splash10-0006-9000000000-d938a8b7afe1aa507d68	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 20V, Negative-QTOF	splash10-0udi-0900000000-de716f6f47c92c7e52f6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran 40V, Negative-QTOF	splash10-0fdn-1900000000-20a3f00fe5c922403365	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB003823

KNApSAcK ID

C00055062

Chemspider ID

509626

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

586292

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran (HMDB0302232)

MOL for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

3D MOL for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

3D SDF for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

3D-SDF for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

PDB for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

3D PDB for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

SMILES for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

INCHI for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

Structure for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

3D Structure for HMDB0302232 (3,6-Dimethyl-2,3,4,5,8,9-hexahydrobenzofuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra