NP-MRD: Showing NP-Card for (2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0216456)

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Record Information

Version

2.0

Created at

2022-09-05 16:26:08 UTC

Updated at

2022-09-05 16:26:08 UTC

NP-MRD ID

NP0216456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

Description

Goniolactone E belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. (2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one is found in Goniothalamus cheliensis. Based on a literature review very few articles have been published on Goniolactone E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218262D          

 35 40  0  0  1  0            999 V2000
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   -4.4363   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9514   -3.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1668   -3.3937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3822   -3.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973   -3.8062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0723   -3.8062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6598   -3.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1652   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8152   -4.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0527    0.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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    7.8936    0.3331    2.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7681    1.2252    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052218262D          

 35 40  0  0  1  0            999 V2000
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   -4.4363   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9514   -3.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1668   -3.3937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0216456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C(=O)C[C@H](OC2=CC(O[C@H]([C@@H]2C[C@H]3OC(=O)C[C@H]3O2)C2=CC=CC=C2)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O7/c29-19-11-18(12-24-27(19)20(30)13-21(33-24)16-7-3-1-4-8-16)32-28(17-9-5-2-6-10-17)25-14-22-23(34-25)15-26(31)35-22/h1-12,21-23,25,28-29H,13-15H2/t21-,22+,23+,25-,28-/m0/s1

> <INCHI_KEY>
FBEFSQXVOZIBTF-WHLVAYQISA-N

> <FORMULA>
C28H24O7

> <MOLECULAR_WEIGHT>
472.493

> <EXACT_MASS>
472.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.47810453380499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-[(S)-[(2S,3aR,6aR)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
4.77893327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.913884626952285

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.671159323510373

> <JCHEM_PKA_STRONGEST_BASIC>
-4.071306182831079

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
124.60860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-[(S)-[(2S,3aR,6aR)-5-oxo-tetrahydro-2H-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -9.821  -7.105   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.281  -7.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.376  -5.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.911  -6.335   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.447  -5.859   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.542  -7.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.002  -7.105   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.232  -5.771   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.308  -5.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.078  -7.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.618  -7.105   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.388  -8.438   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.388  -5.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.618  -4.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.078  -4.437   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.388  -3.104   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.928  -3.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.698  -1.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.928  -0.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.698   0.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.238   0.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.008  -0.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.238  -1.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.698  -4.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.928  -5.771   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.698  -7.105   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.232  -8.438   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.308  -8.438   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.078  -9.772   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.308 -11.106   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.232 -11.106   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.002  -9.772   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.447  -8.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.911  -7.875   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.376  -8.351   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   17   25                                                       
CONECT   25   24   13   26                                                  
CONECT   26   25                                                            
CONECT   27    7   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33    6   34                                                       
CONECT   34   33    4   35                                                  
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₄O₇

Average Mass

472.4930 Da

Monoisotopic Mass

472.15220 Da

IUPAC Name

(2S)-7-[(S)-[(2S,3aR,6aR)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-7-[(S)-[(2S,3aR,6aR)-5-oxo-tetrahydro-2H-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=C2C(=O)C[C@H](OC2=CC(O[C@H]([C@@H]2C[C@H]3OC(=O)C[C@H]3O2)C2=CC=CC=C2)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H24O7/c29-19-11-18(12-24-27(19)20(30)13-21(33-24)16-7-3-1-4-8-16)32-28(17-9-5-2-6-10-17)25-14-22-23(34-25)15-26(31)35-22/h1-12,21-23,25,28-29H,13-15H2/t21-,22+,23+,25-,28-/m0/s1

InChI Key

FBEFSQXVOZIBTF-WHLVAYQISA-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 cheliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Hydroxyflavonoid
Flavanone
5-hydroxyflavonoid
Chromone
1-benzopyran
Chromane
Benzopyran
Furofuran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Oxolane
Vinylogous acid
Carboxylic acid ester
Lactone
Ketone
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aldehyde
Organic oxide
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	4.78	ChemAxon
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.61 m³·mol⁻¹	ChemAxon
Polarizability	48.48 Å³	ChemAxon
Number of Rings	6	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

C00045978

Chemspider ID

9987403

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11812741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0216456)

MOL for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0216456 ((2s)-7-[(s)-[(2s,3ar,6ar)-5-oxo-tetrahydro-2h-furo[3,2-b]furan-2-yl](phenyl)methoxy]-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)