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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:20:55 UTC

Update Date

2022-03-07 02:56:43 UTC

HMDB ID

HMDB0040766

Secondary Accession Numbers

HMDB40766

Metabolite Identification

Common Name

Anethofuran

Description

Anethofuran belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Anethofuran is a dill tasting compound. Anethofuran has been detected, but not quantified in, dills (Anethum graveolens) and herbs and spices. This could make anethofuran a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Anethofuran.

Structure

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

COMPND    HMDB0040766
HETATM    1  C1  UNL     1       3.391   0.256   0.578  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.986   0.153   0.039  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.384  -1.031  -0.054  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.029  -1.054  -0.583  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.859  -2.158  -0.160  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.155  -1.636  -0.091  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.080  -0.269  -0.343  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.184   0.514   0.272  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.714   0.094   0.133  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.152   1.356  -0.438  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.349   1.423  -0.365  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.941  -0.693   0.466  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.956   1.020   0.005  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.309   0.615   1.608  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.936  -1.900   0.268  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.049  -0.815  -1.661  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.587  -2.430   0.901  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.817  -3.068  -0.792  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.072  -0.168  -1.468  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.815   0.940  -0.561  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.835  -0.058   0.938  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.729   1.416   0.767  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.558  -0.045   1.201  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.539   1.458  -1.476  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.549   2.203   0.162  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.711   1.659  -1.394  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.700   2.220   0.339  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   17   18
CONECT    6    7
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
2,3,3a,4,5,7a-hexahydro-3,6-Dimethylbenzofuran, 9ci	HMDB
3,6-Dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran	HMDB
3,6-Dimethyl-2,3,3a,4,5,7a-hexahydrobenzofuran	HMDB
3,7-Dimethyl-4,5,6,9-tetrahydrocoumaran	HMDB
3,9-Epoxy-1-P-menthene	HMDB
Dill ether	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

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

CAS Registry Number

70786-44-6

SMILES

CC1OCC2C=C(C)CCC12

InChI Identifier

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

InChI Key

DBDSRLQPJKTGQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
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

Physiological effect

Organoleptic effect

Odor

Dill

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040766)
Cytoplasm (HMDB: HMDB0040766)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040766)

Source

Exogenous

Exogenous (HMDB: HMDB0040766)

Food

Food (HMDB: HMDB0040766)

Herb and spice

Herb

Dill (FooDB: FOOD00013)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040766)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0040766)

Biological role

Nutrient (HMDB: HMDB0040766)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	207.00 to 208.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	2.576 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-4.1	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	46.71 m³·mol⁻¹	ChemAxon
Polarizability	18.39 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]+	135.295	31661259
DarkChem	[M-H]-	129.291	31661259
DeepCCS	[M-2H]-	172.651	30932474
DeepCCS	[M+Na]+	148.027	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	136.9	32859911
AllCCS	[M+Na]+	138.1	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	141.2	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.	4.72 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9241 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2187.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	576.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	338.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	610.9 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	695.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	143.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1280.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	434.3 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	1286.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	568.4 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	23.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anethofuran	CC1OCC2C=C(C)CCC12	1577.0	Standard polar	33892256
Anethofuran	CC1OCC2C=C(C)CCC12	1177.9	Standard non polar	33892256
Anethofuran	CC1OCC2C=C(C)CCC12	1185.6	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 - Anethofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ox-9700000000-73bee477974d31c8dd6d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anethofuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anethofuran 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 - Anethofuran 10V, Positive-QTOF	splash10-0udi-0900000000-ee45d7b0c89f3a812d71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 20V, Positive-QTOF	splash10-0udi-3900000000-afbae20abe9a3bf67887	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 40V, Positive-QTOF	splash10-0pvi-9100000000-011eafd0d4a01053591f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 10V, Negative-QTOF	splash10-0udi-0900000000-6ebf424524bdac5e1ffe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 20V, Negative-QTOF	splash10-0udi-0900000000-09de5ab77a0a8e1df453	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 40V, Negative-QTOF	splash10-05tf-4900000000-ccb71622a804193ac25e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 20V, Negative-QTOF	splash10-0udi-0900000000-ef9d0a438bc0672b1a39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 40V, Negative-QTOF	splash10-0006-7900000000-366b79432d93e18b4133	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 10V, Positive-QTOF	splash10-0udi-0900000000-0250a390f927b022dd08	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 20V, Positive-QTOF	splash10-0pbi-6900000000-4ed0414891e9d698330c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anethofuran 40V, Positive-QTOF	splash10-05n3-9300000000-fcef5d498e3e40db2621	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020582

KNApSAcK ID

C00055062

Chemspider ID

35015019

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

rw1593891

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 Anethofuran (HMDB0040766)

MOL for HMDB0040766 (Anethofuran)

3D MOL for HMDB0040766 (Anethofuran)

3D SDF for HMDB0040766 (Anethofuran)

3D-SDF for HMDB0040766 (Anethofuran)

PDB for HMDB0040766 (Anethofuran)

3D PDB for HMDB0040766 (Anethofuran)

SMILES for HMDB0040766 (Anethofuran)

INCHI for HMDB0040766 (Anethofuran)

Structure for HMDB0040766 (Anethofuran)

3D Structure for HMDB0040766 (Anethofuran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra