NP-MRD: Showing NP-Card for (5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan (NP0154824)

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Record Information

Version

2.0

Created at

2022-09-02 11:47:45 UTC

Updated at

2022-09-02 11:47:45 UTC

NP-MRD ID

NP0154824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan

Description

3,5Beta-Dimethyl-4-(methoxymethyl)-9-methoxy-5,6-dihydronaphtho[2,3-b]furan belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan is found in Trichilia martiana. Based on a literature review very few articles have been published on 3,5beta-Dimethyl-4-(methoxymethyl)-9-methoxy-5,6-dihydronaphtho[2,3-b]furan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    3.3987    2.2456   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699    1.9322   -0.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.5835   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -0.0430    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035    0.6313    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.0870    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6493   -1.4681    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7925   -2.1635    0.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -2.6741    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -2.1220    0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -3.4014    0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -3.6169    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275   -2.3876    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -2.1865   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338   -1.4582    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    0.6179    0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025    1.9293    0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    2.7895    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    2.0941    0.1456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4024    2.3137   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5434    3.3315   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878    1.7533   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781    1.8279    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    0.0441   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6118    0.3653    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4040   -1.8794   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301   -3.4459    0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326   -3.1416   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6110   -4.5674    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.5330    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -2.0854   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301   -3.2127   -0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632    0.0208    1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913    2.4101    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083    3.3651    1.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    3.5374   -0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651    2.5347    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4693    2.4609   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    1.4383   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    3.2473   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  7  2  0
  7  8  1  0
  8  9  1  0
  7  6  1  0
  6  5  2  0
  5 19  1  0
 19 20  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
  5  4  1  0
 10 15  1  0
 16  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 12 29  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 19 37  1  1
 20 38  1  0
 20 39  1  0
 20 40  1  0
 18 35  1  0
 18 36  1  0
 17 34  1  0
 16 33  1  0
M  END


  Mrv1652309022213472D          

 20 22  0  0  1  0            999 V2000
   -0.0734   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4 15  2  0  0  0  0
 10 15  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0154824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1=C2C(C)=COC2=C(OC)C2=C1[C@@H](C)CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O3/c1-10-6-5-7-12-14(10)13(9-18-3)15-11(2)8-20-17(15)16(12)19-4/h5,7-8,10H,6,9H2,1-4H3/t10-/m0/s1

> <INCHI_KEY>
CGLAZNJYDWVCGA-JTQLQIEISA-N

> <FORMULA>
C17H20O3

> <MOLECULAR_WEIGHT>
272.344

> <EXACT_MASS>
272.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.75125988107707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5H,6H-naphtho[2,3-b]furan

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
3.8239477223333336

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8103312162519054

> <JCHEM_POLAR_SURFACE_AREA>
31.6

> <JCHEM_REFRACTIVITY>
81.118

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5H,6H-naphtho[2,3-b]furan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.137  -9.003   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.137  -7.463   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.197  -6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.197  -0.533   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.137   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.602  -2.367   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.602  -4.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.077  -6.323   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.864  -6.693   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4   10                                                  
CONECT   16    6   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,5b-Dimethyl-4-(methoxymethyl)-9-methoxy-5,6-dihydronaphtho[2,3-b]furan	Generator
3,5Β-dimethyl-4-(methoxymethyl)-9-methoxy-5,6-dihydronaphtho[2,3-b]furan	Generator

Chemical Formula

C₁₇H₂₀O₃

Average Mass

272.3440 Da

Monoisotopic Mass

272.14124 Da

IUPAC Name

(5S)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5H,6H-naphtho[2,3-b]furan

Traditional Name

(5S)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5H,6H-naphtho[2,3-b]furan

CAS Registry Number

Not Available

SMILES

COCC1=C2C(C)=COC2=C(OC)C2=C1[C@@H](C)CC=C2

InChI Identifier

InChI=1S/C17H20O3/c1-10-6-5-7-12-14(10)13(9-18-3)15-11(2)8-20-17(15)16(12)19-4/h5,7-8,10H,6,9H2,1-4H3/t10-/m0/s1

InChI Key

CGLAZNJYDWVCGA-JTQLQIEISA-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
Trichilia martiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Naphthalene
Benzofuran
Anisole
Phenol ether
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	4.4	ALOGPS
logP	3.82	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	31.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.12 m³·mol⁻¹	ChemAxon
Polarizability	30.75 Å³	ChemAxon
Number of Rings	3	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

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

101410363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan (NP0154824)

MOL for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

3D MOL for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

3D SDF for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

3D-SDF for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

PDB for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

3D PDB for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

SMILES for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

INCHI for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

Structure for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)

3D Structure for NP0154824 ((5s)-9-methoxy-4-(methoxymethyl)-3,5-dimethyl-5h,6h-naphtho[2,3-b]furan)