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

2012-05-18 15:59:04 UTC

Update Date

2023-02-21 17:18:04 UTC

HMDB ID

HMDB0013815

Secondary Accession Numbers

HMDB13815

Metabolite Identification

Common Name

2,3-Dihydrobenzofuran

Description

2,3-Dihydrobenzofuran, also known as coumaran or dihydrocoumarone, belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. 2,3-Dihydrobenzofuran has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2,3-dihydrobenzofuran a potential biomarker for the consumption of these foods. 2,3-Dihydrobenzofuran is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2,3-Dihydrobenzofuran.

Structure

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

10329
  Mrv1652304062013022D          

 17 18  0  0  0  0            999 V2000
    3.8597   -0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030    0.9191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525    1.1316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213   -0.3421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    0.3421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    0.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4 12  1  0  0  0  0
  4 13  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  7  9  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  2  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013815

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C1=C([H])C([H])=C2C(OC([H])([H])C2([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2

> <INCHI_KEY>
HBEDSQVIWPRPAY-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.061186017302038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydro-1-benzofuran

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.8554630566666663

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.843615976718837

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
35.830799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydrobenzofuran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 10329                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       7.205  -1.239   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.205   1.239   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.104   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       8.032   1.716   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0       6.818   2.112   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       8.813  -0.639   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       8.813   0.639   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       4.414   2.495   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.414  -2.495   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.253   1.247   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       2.253  -1.247   0.000  0.00  0.00           H+0
CONECT    1    4    5                                                       
CONECT    2    3    4   10   11                                             
CONECT    3    2    5    6                                                  
CONECT    4    1    2   12   13                                             
CONECT    5    1    3    7                                                  
CONECT    6    3    8   14                                                  
CONECT    7    5    9   15                                                  
CONECT    8    6    9   16                                                  
CONECT    9    7    8   17                                                  
CONECT   10    2                                                            
CONECT   11    2                                                            
CONECT   12    4                                                            
CONECT   13    4                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Coumaran	ChEBI
2,3-Dihydro-1-benzofuran	HMDB
2,3-Dihydro-benzofura	HMDB
2,3-Dihydrobenzofurane	HMDB
Coumaran (2,3-dihydrobenzofuran)	HMDB
Dihydrobenzofuran	HMDB
Dihydrocoumarone	HMDB
Kumaran	HMDB

Chemical Formula

C₈H₈O

Average Molecular Weight

120.1485

Monoisotopic Molecular Weight

120.057514878

IUPAC Name

2,3-dihydro-1-benzofuran

Traditional Name

2,3-dihydrobenzofuran

CAS Registry Number

496-16-2

SMILES

[H]C1=C([H])C([H])=C2C(OC([H])([H])C2([H])[H])=C1[H]

InChI Identifier

InChI=1S/C8H8O/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2

InChI Key

HBEDSQVIWPRPAY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:87607 )

Ontology

Not Available

Urine (HMDB: HMDB0013815)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-21.5 °C	Not Available
Boiling Point	188.00 to 189.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1491 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.14	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.27 g/L	ALOGPS
logP	2.16	ALOGPS
logP	1.86	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-4.8	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	35.83 m³·mol⁻¹	ChemAxon
Polarizability	13.06 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]+	122.717	31661259
DarkChem	[M-H]-	120.666	31661259
DeepCCS	[M+H]+	142.56	30932474
DeepCCS	[M-H]-	140.262	30932474
DeepCCS	[M-2H]-	175.808	30932474
DeepCCS	[M+Na]+	150.968	30932474
AllCCS	[M+H]+	123.3	32859911
AllCCS	[M+H-H2O]+	118.6	32859911
AllCCS	[M+NH4]+	127.7	32859911
AllCCS	[M+Na]+	128.9	32859911
AllCCS	[M-H]-	120.4	32859911
AllCCS	[M+Na-2H]-	121.8	32859911
AllCCS	[M+HCOO]-	123.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydrobenzofuran	[H]C1=C([H])C([H])=C2C(OC([H])([H])C2([H])[H])=C1[H]	2047.1	Standard polar	33892256
2,3-Dihydrobenzofuran	[H]C1=C([H])C([H])=C2C(OC([H])([H])C2([H])[H])=C1[H]	1116.2	Standard non polar	33892256
2,3-Dihydrobenzofuran	[H]C1=C([H])C([H])=C2C(OC([H])([H])C2([H])[H])=C1[H]	1089.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,3-Dihydrobenzofuran EI-B (Non-derivatized)	splash10-00dl-9800000000-3ba67e4900f8c1b81fb5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dihydrobenzofuran EI-B (Non-derivatized)	splash10-00dl-9800000000-3ba67e4900f8c1b81fb5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydrobenzofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7900000000-c21f5fa889e8b36e3316	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydrobenzofuran 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 - 2,3-Dihydrobenzofuran 10V, Positive-QTOF	splash10-00di-0900000000-6da2aec60f8895cb7391	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 20V, Positive-QTOF	splash10-00di-2900000000-dacf2ec132313979105e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 40V, Positive-QTOF	splash10-0fb9-9100000000-0901a78bdaa1deb059a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 10V, Negative-QTOF	splash10-014i-0900000000-9cb5cffa8f708c5ff3b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 20V, Negative-QTOF	splash10-014i-0900000000-42fe63a2d1e38c49f301	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 40V, Negative-QTOF	splash10-004l-9000000000-91b4ff7bfea476c008e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 10V, Positive-QTOF	splash10-00di-0900000000-b29a5171701d3aae862e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 20V, Positive-QTOF	splash10-00di-2900000000-2f072e905eae5ae48cd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 40V, Positive-QTOF	splash10-0fvl-9100000000-e75a80de77f1731153a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 10V, Negative-QTOF	splash10-014i-0900000000-972f865a96261dcb891a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 20V, Negative-QTOF	splash10-014l-8900000000-481312547ceb5b95479c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydrobenzofuran 40V, Negative-QTOF	splash10-0006-9600000000-cfbc92962f7022af1386	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zhang, S., Liu, L...	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

FDB111651

KNApSAcK ID

C00039027

Chemspider ID

21106522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10329

PDB ID

Not Available

ChEBI ID

87607

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1161681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2,3-Dihydrobenzofuran (HMDB0013815)

MOL for HMDB0013815 (2,3-Dihydrobenzofuran)

3D MOL for HMDB0013815 (2,3-Dihydrobenzofuran)

3D SDF for HMDB0013815 (2,3-Dihydrobenzofuran)

3D-SDF for HMDB0013815 (2,3-Dihydrobenzofuran)

PDB for HMDB0013815 (2,3-Dihydrobenzofuran)

3D PDB for HMDB0013815 (2,3-Dihydrobenzofuran)

SMILES for HMDB0013815 (2,3-Dihydrobenzofuran)

INCHI for HMDB0013815 (2,3-Dihydrobenzofuran)

Structure for HMDB0013815 (2,3-Dihydrobenzofuran)

3D Structure for HMDB0013815 (2,3-Dihydrobenzofuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra