NP-MRD: Showing NP-Card for 2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0284815)

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Record Information

Version

2.0

Created at

2022-09-09 12:42:11 UTC

Updated at

2022-09-09 12:42:11 UTC

NP-MRD ID

NP0284815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(7'R,8'R)-4,7'-Epoxy-3'-methoxy-4',5,9,9'-lignanetetrol 9'-glucoside belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety (7'R,8'R)-4,7'-Epoxy-3'-methoxy-4',5,9,9'-lignanetetrol 9'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (7'R,8'R)-4,7'-Epoxy-3'-methoxy-4',5,9,9'-lignanetetrol 9'-glucoside has been detected, but not quantified in, alcoholic beverages. 2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Breynia fruticosa. This could make (7'r,8'r)-4,7'-epoxy-3'-methoxy-4',5,9,9'-lignanetetrol 9'-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310362D          

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  Mrv0541 05061310362D          

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 26  6  1  0  0  0  0
 27 10  1  0  0  0  0
 28 16  1  0  0  0  0
 29 17  1  0  0  0  0
 30 20  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 33  1  1  0  0  0  0
 33 18  1  0  0  0  0
 34 11  1  0  0  0  0
 34 25  1  0  0  0  0
 35 19  1  0  0  0  0
 35 25  1  0  0  0  0
 36 23  1  0  0  0  0
 36 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1OC2=C(C=C(CCCO)C=C2O)C1COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O11/c1-33-18-9-13(4-5-16(18)28)23-15(11-34-25-22(32)21(31)20(30)19(10-27)35-25)14-7-12(3-2-6-26)8-17(29)24(14)36-23/h4-5,7-9,15,19-23,25-32H,2-3,6,10-11H2,1H3

> <INCHI_KEY>
IZPTZYWDXAUURH-UHFFFAOYSA-N

> <FORMULA>
C25H32O11

> <MOLECULAR_WEIGHT>
508.515

> <EXACT_MASS>
508.194461866

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
52.54703425798637

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.039796728666667

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.244999383759959

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.642315277420844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3774160818141397

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
125.42529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -7.333   0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.215  -3.757   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.708  -3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.678  -4.582   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.171  -4.262   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.695  -2.797   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.726  -1.653   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.199   2.073   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.691  -5.222   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.154  -6.046   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.141  -5.406   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.189  -2.477   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.793   0.175   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.250  -0.188   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.232  -1.973   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   33                                                            
CONECT    2    3    6                                                       
CONECT    3    2   12                                                       
CONECT    4    5   13                                                       
CONECT    5    4   16                                                       
CONECT    6    2   26                                                       
CONECT    7   12   14                                                       
CONECT    8   12   17                                                       
CONECT    9   13   18                                                       
CONECT   10   19   27                                                       
CONECT   11   15   34                                                       
CONECT   12    3    7    8                                                  
CONECT   13    4    9   23                                                  
CONECT   14    7   15   24                                                  
CONECT   15   11   14   23                                                  
CONECT   16    5   18   28                                                  
CONECT   17    8   24   29                                                  
CONECT   18    9   16   33                                                  
CONECT   19   10   20   35                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22   31                                                  
CONECT   22   21   25   32                                                  
CONECT   23   13   15   36                                                  
CONECT   24   14   17   36                                                  
CONECT   25   22   34   35                                                  
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33    1   18                                                       
CONECT   34   11   25                                                       
CONECT   35   19   25                                                       
CONECT   36   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₁

Average Mass

508.5150 Da

Monoisotopic Mass

508.19446 Da

IUPAC Name

2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1OC2=C(C=C(CCCO)C=C2O)C1COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C25H32O11/c1-33-18-9-13(4-5-16(18)28)23-15(11-34-25-22(32)21(31)20(30)19(10-27)35-25)14-7-12(3-2-6-26)8-17(29)24(14)36-23/h4-5,7-9,15,19-23,25-32H,2-3,6,10-11H2,1H3

InChI Key

IZPTZYWDXAUURH-UHFFFAOYSA-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
Breynia fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Lignan glycoside
Neolignan skeleton
Norlignan skeleton
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Coumaran
Benzofuran
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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	0.46	ALOGPS
logP	0.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.43 m³·mol⁻¹	ChemAxon
Polarizability	52.55 Å³	ChemAxon
Number of Rings	4	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

HMDB0038710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018118

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

131752438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0284815)

MOL for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0284815 (2-{[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)