NP-MRD: Showing NP-Card for (3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one (NP0159527)

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Record Information

Version

2.0

Created at

2022-09-02 17:17:44 UTC

Updated at

2022-09-02 17:17:44 UTC

NP-MRD ID

NP0159527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one

Description

(+)-Goniofufurone belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one is found in Goniothalamus aruensis, Goniothalamus borneensis, Goniothalamus cardiopetalus and Goniothalamus giganteus. (3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one was first documented in 2018 (PMID: 30746062). Based on a literature review very few articles have been published on (+)-Goniofufurone (PMID: 31480006).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.2463   -3.1318   -1.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904   -1.8972   -1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572   -1.2255   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    0.0983   -0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9960   -0.0241    0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042   -0.0539    0.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3141    0.4070    1.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0888    1.7116    1.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.1832    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766    1.0558   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474    0.7725   -0.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -0.3543   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.2430    0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3531   -0.9418    1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543    0.8548   -0.8589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9674    2.1521   -0.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    0.3687   -1.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8803   -0.8918   -2.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808   -1.7612    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4499   -0.9962   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6392    0.8866   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.0533    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -0.2299    2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118    2.3814    1.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743    1.9500   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0501    1.4391   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -0.5878   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1306   -2.1467    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163   -1.6714    1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    0.7278   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    2.1061    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    1.1147   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 15  6  1  0
 14  9  1  0
 17  4  1  0
  8 24  1  0
  7 23  1  1
  6 22  1  6
  4 21  1  1
  3 19  1  0
  3 20  1  0
 17 32  1  6
 15 30  1  6
 16 31  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
M  END


  Mrv1652309022219172D          

 18 20  0  0  1  0            999 V2000
   -0.0404   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1487   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5612    0.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7987   -1.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487   -1.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0937   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]([C@H]1O[C@@H]2CC(=O)O[C@@H]2[C@H]1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c14-9-6-8-12(18-9)11(16)13(17-8)10(15)7-4-2-1-3-5-7/h1-5,8,10-13,15-16H,6H2/t8-,10-,11-,12+,13-/m1/s1

> <INCHI_KEY>
OGSSCWFZICJOMO-ZGYLKHSLSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.25

> <EXACT_MASS>
250.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.422017207736097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,5R,6S,6aR)-6-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-hexahydrofuro[3,2-b]furan-2-one

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
0.2854940923333337

> <ALOGPS_LOGS>
-0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.645493196456346

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.863895775852626

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5013569344069326

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
60.17580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,5R,6S,6aR)-6-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-tetrahydro-3H-furo[3,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0      -0.075  -0.476   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.299   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.744  -0.476   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.514   0.858   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.514  -1.810   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.054  -1.810   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.824  -3.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.054  -4.477   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.514  -4.477   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.744  -3.143   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.775  -3.186   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.370  -1.722   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4   18                                                  
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₅

Average Mass

250.2500 Da

Monoisotopic Mass

250.08412 Da

IUPAC Name

(3aR,5R,6S,6aR)-6-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-hexahydrofuro[3,2-b]furan-2-one

Traditional Name

(3aR,5R,6S,6aR)-6-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-tetrahydro-3H-furo[3,2-b]furan-2-one

CAS Registry Number

Not Available

SMILES

O[C@@H]([C@H]1O[C@@H]2CC(=O)O[C@@H]2[C@H]1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H14O5/c14-9-6-8-12(18-9)11(16)13(17-8)10(15)7-4-2-1-3-5-7/h1-5,8,10-13,15-16H,6H2/t8-,10-,11-,12+,13-/m1/s1

InChI Key

OGSSCWFZICJOMO-ZGYLKHSLSA-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
Goniothalamus aruensis	LOTUS Database	35616633
Goniothalamus borneensis	LOTUS Database	35616633
Goniothalamus cardiopetalus	LOTUS Database	35616633
Goniothalamus giganteus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Monosaccharide
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic alcohol
Alcohol
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	0.06	ALOGPS
logP	0.29	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.18 m³·mol⁻¹	ChemAxon
Polarizability	24.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

9272129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11096987

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vukic VR, Loncar DM, Vukic DV, Jevric LR, Benedekovic G, Francuz J, Kojic V, Karadzic Banjac MZ, Popsavin V: In vitro antitumor activity, ADME-Tox and 3D-QSAR of synthesized and selected natural styryl lactones. Comput Biol Chem. 2019 Dec;83:107112. doi: 10.1016/j.compbiolchem.2019.107112. Epub 2019 Aug 23. [PubMed:31480006 ]
Francuz J, Popsavin M, Djokic S, Kojic V, Srdic-Rajic T, Rodic MV, Jakimov D, Popsavin V: Novel O-methyl goniofufurone and 7-epi-goniofufurone derivatives: synthesis, in vitro cytotoxicity and SAR analysis. Medchemcomm. 2018 Oct 26;9(12):2017-2027. doi: 10.1039/c8md00431e. eCollection 2018 Dec 1. [PubMed:30746062 ]
LOTUS database [Link]

Showing NP-Card for (3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one (NP0159527)

MOL for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

3D MOL for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

3D SDF for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

3D-SDF for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

PDB for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

3D PDB for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

SMILES for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

INCHI for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

Structure for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)

3D Structure for NP0159527 ((3ar,5r,6s,6ar)-6-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-tetrahydro-3h-furo[3,2-b]furan-2-one)