NP-MRD: Showing NP-Card for (3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one (NP0200581)

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Record Information

Version

2.0

Created at

2022-09-04 19:27:33 UTC

Updated at

2022-09-04 19:27:34 UTC

NP-MRD ID

NP0200581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one

Description

(3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-1,3-dihydro-2-benzofuran-1-one belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. (3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one is found in Stereocaulon alpinum. Based on a literature review very few articles have been published on (3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-1,3-dihydro-2-benzofuran-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221272D          

 32 34  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7238   -7.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042221272D          

 32 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0200581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(O)=CC(O)=C1OC1=CC(OC)=CC2=C1C(=O)O[C@@]2(CCCC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-5-7-9-10-16-12-17(26)13-20(27)23(16)31-21-15-18(29-3)14-19-22(21)24(28)32-25(19,30-4)11-8-6-2/h12-15,26-27H,5-11H2,1-4H3/t25-/m1/s1

> <INCHI_KEY>
SIFVKFNQJLVAOD-RUZDIDTESA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.8376184991708

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-1,3-dihydro-2-benzofuran-1-one

> <JCHEM_LOGP>
6.608107150333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.635049118238193

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.541324842010864

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6411797545617026

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
121.2226

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.191 -12.580   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.685 -12.260   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.818 -13.987   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.349 -13.826   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.685 -15.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.155 -15.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.491 -17.293   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.960 -17.753   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.809 -14.318   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.964 -13.299   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   15   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   21   27   31                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   26   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₇

Average Mass

444.5240 Da

Monoisotopic Mass

444.21480 Da

IUPAC Name

(3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

(3R)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=CC(O)=C1OC1=CC(OC)=CC2=C1C(=O)O[C@@]2(CCCC)OC

InChI Identifier

InChI=1S/C25H32O7/c1-5-7-9-10-16-12-17(26)13-20(27)23(16)31-21-15-18(29-3)14-19-22(21)24(28)32-25(19,30-4)11-8-6-2/h12-15,26-27H,5-11H2,1-4H3/t25-/m1/s1

InChI Key

SIFVKFNQJLVAOD-RUZDIDTESA-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
Stereocaulon alpinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Benzofuranone
Phthalide
Isobenzofuranone
Isocoumaran
Anisole
Resorcinol
Phenol ether
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	6.61	ChemAxon
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	121.22 m³·mol⁻¹	ChemAxon
Polarizability	48.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162843817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one (NP0200581)

MOL for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

3D MOL for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

3D SDF for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

3D-SDF for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

PDB for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

3D PDB for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

SMILES for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

INCHI for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

Structure for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)

3D Structure for NP0200581 ((3r)-3-butyl-7-(2,4-dihydroxy-6-pentylphenoxy)-3,5-dimethoxy-2-benzofuran-1-one)