NP-MRD: Showing NP-Card for (2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde (NP0194693)

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Record Information

Version

2.0

Created at

2022-09-04 12:24:11 UTC

Updated at

2022-09-04 12:24:11 UTC

NP-MRD ID

NP0194693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

Description

Fomannoxin 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. (2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde is found in Heterobasidion annosum and Lauriliella taxodii. (2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde was first documented in 2014 (PMID: 25260338). Based on a literature review a small amount of articles have been published on Fomannoxin (PMID: 27104866) (PMID: 28055210) (PMID: 32075201) (PMID: 29376877).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214242D          

 14 15  0  0  1  0            999 V2000
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC2=CC(C=O)=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O2/c1-8(2)12-6-10-5-9(7-13)3-4-11(10)14-12/h3-5,7,12H,1,6H2,2H3/t12-/m0/s1

> <INCHI_KEY>
MPEXJCQZHBHGMC-LBPRGKRZSA-N

> <FORMULA>
C12H12O2

> <MOLECULAR_WEIGHT>
188.226

> <EXACT_MASS>
188.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.475550769201167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

> <JCHEM_LOGP>
2.6023435663333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.891178368937205

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
55.52970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydro-2-(1-methylethenyl)-5-benzofurancarboxaldehyde	MeSH

Chemical Formula

C₁₂H₁₂O₂

Average Mass

188.2260 Da

Monoisotopic Mass

188.08373 Da

IUPAC Name

(2S)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

Traditional Name

(2S)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC2=CC(C=O)=CC=C2O1

InChI Identifier

InChI=1S/C12H12O2/c1-8(2)12-6-10-5-9(7-13)3-4-11(10)14-12/h3-5,7,12H,1,6H2,2H3/t12-/m0/s1

InChI Key

MPEXJCQZHBHGMC-LBPRGKRZSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Heterobasidion annosum	LOTUS Database	35616633
Lauriliella taxodii	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
Aryl-aldehyde
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.6	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.53 m³·mol⁻¹	ChemAxon
Polarizability	20.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043506

Chemspider ID

143094

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163013

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hansson D, Wubshet S, Olson A, Karlsson M, Staerk D, Broberg A: Secondary metabolite comparison of the species within the Heterobasidion annosum s.l. complex. Phytochemistry. 2014 Dec;108:243-51. doi: 10.1016/j.phytochem.2014.08.028. Epub 2014 Sep 23. [PubMed:25260338 ]
Schwenk D, Brandt P, Blanchette RA, Nett M, Hoffmeister D: Unexpected Metabolic Versatility in a Combined Fungal Fomannoxin/Vibralactone Biosynthesis. J Nat Prod. 2016 May 27;79(5):1407-14. doi: 10.1021/acs.jnatprod.6b00147. Epub 2016 Apr 22. [PubMed:27104866 ]
Chang JC, Hsiao G, Lin RK, Kuo YH, Ju YM, Lee TH: Bioactive Constituents from the Termite Nest-Derived Medicinal Fungus Xylaria nigripes. J Nat Prod. 2017 Jan 27;80(1):38-44. doi: 10.1021/acs.jnatprod.6b00249. Epub 2017 Jan 5. [PubMed:28055210 ]
Li P, Su R, Yin R, Lai D, Wang M, Liu Y, Zhou L: Detoxification of Mycotoxins through Biotransformation. Toxins (Basel). 2020 Feb 14;12(2):121. doi: 10.3390/toxins12020121. [PubMed:32075201 ]
Gonzalez-Ramirez M, Gavilan J, Silva-Grecchi T, Cajas-Madriaga D, Trivino S, Becerra J, Saez-Orellana F, Perez C, Fuentealba J: A Natural Benzofuran from the Patagonic Aleurodiscus vitellinus Fungus has Potent Neuroprotective Properties on a Cellular Model of Amyloid-beta Peptide Toxicity. J Alzheimers Dis. 2018;61(4):1463-1475. doi: 10.3233/JAD-170958. [PubMed:29376877 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde (NP0194693)

MOL for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

3D MOL for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

3D SDF for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

3D-SDF for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

PDB for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

3D PDB for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

SMILES for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

INCHI for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

Structure for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)

3D Structure for NP0194693 ((2s)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde)