NP-MRD: Showing NP-Card for 2,3-Dihydrobenzofuran (NP0136243)

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Record Information

Version

2.0

Created at

2022-05-12 15:09:29 UTC

Updated at

2022-05-12 15:09:29 UTC

NP-MRD ID

NP0136243

Secondary Accession Numbers

None

Natural Product 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 is found in Imperata cylindrica, Phyla nodiflora, Trigonella foenum-graecum and Vitis vinifera. 2,3-Dihydrobenzofuran was first documented in 2013 (PMID: 24078598). 2,3-Dihydrobenzofuran is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 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>
NP0136243

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

120.1485 Da

Monoisotopic Mass

120.05751 Da

IUPAC Name

2,3-dihydro-1-benzofuran

Traditional Name

2,3-dihydrobenzofuran

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Imperata cylindrica	LOTUS Database	35616633
Lippia nodiflora	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0013815

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

Good Scents ID

Not Available

References

General References

Kus PM, Jerkovic I, Tuberoso CI, Sarolic M: The volatile profiles of a rare apple (Malus domestica Borkh.) honey: shikimic acid-pathway derivatives, terpenes, and others. Chem Biodivers. 2013 Sep;10(9):1638-52. doi: 10.1002/cbdv.201200404. [PubMed:24078598 ]

Showing NP-Card for 2,3-Dihydrobenzofuran (NP0136243)

MOL for NP0136243 (2,3-Dihydrobenzofuran)

3D MOL for NP0136243 (2,3-Dihydrobenzofuran)

3D SDF for NP0136243 (2,3-Dihydrobenzofuran)

3D-SDF for NP0136243 (2,3-Dihydrobenzofuran)

PDB for NP0136243 (2,3-Dihydrobenzofuran)

3D PDB for NP0136243 (2,3-Dihydrobenzofuran)

SMILES for NP0136243 (2,3-Dihydrobenzofuran)

INCHI for NP0136243 (2,3-Dihydrobenzofuran)

Structure for NP0136243 (2,3-Dihydrobenzofuran)

3D Structure for NP0136243 (2,3-Dihydrobenzofuran)