NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol (NP0160164)

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Record Information

Version

2.0

Created at

2022-09-02 18:03:19 UTC

Updated at

2022-09-02 18:03:19 UTC

NP-MRD ID

NP0160164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

Description

2,3-Dihydro-2beta-[4-(alpha-L-rhamnopyranosyloxy)-3-methoxyphenyl]-3beta-(hydroxymethyl)-5-(3-hydroxypropyl)benzofuran-7-ol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol is found in Picea abies, Pinus massoniana, Pinus sibirica and Pinus sylvestris. Based on a literature review very few articles have been published on 2,3-Dihydro-2beta-[4-(alpha-L-rhamnopyranosyloxy)-3-methoxyphenyl]-3beta-(hydroxymethyl)-5-(3-hydroxypropyl)benzofuran-7-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220032D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309022220032D          

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 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0160164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)[C@@H]1OC2=C(O)C=C(CCCO)C=C2[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O10/c1-12-20(29)21(30)22(31)25(33-12)34-18-6-5-14(10-19(18)32-2)23-16(11-27)15-8-13(4-3-7-26)9-17(28)24(15)35-23/h5-6,8-10,12,16,20-23,25-31H,3-4,7,11H2,1-2H3/t12-,16-,20-,21+,22+,23-,25-/m0/s1

> <INCHI_KEY>
PHHIEOZUONPPQY-QDCFJCCASA-N

> <FORMULA>
C25H32O10

> <MOLECULAR_WEIGHT>
492.521

> <EXACT_MASS>
492.19954723

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.74232299578301

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{4-[(2R,3R)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.5894742476666666

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.215328834931933

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.980253416795643

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416081814137

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
123.6127

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{4-[(2R,3R)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol

> <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  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.592  -2.073   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.710   0.031   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.940   1.365   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.710   2.698   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.940   4.032   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.250   2.698   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.020   4.032   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.020   1.365   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.560   1.365   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.250   0.031   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.020  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18    6   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    5   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   26   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydro-2b-[4-(a-L-rhamnopyranosyloxy)-3-methoxyphenyl]-3b-(hydroxymethyl)-5-(3-hydroxypropyl)benzofuran-7-ol	Generator
2,3-Dihydro-2β-[4-(α-L-rhamnopyranosyloxy)-3-methoxyphenyl]-3β-(hydroxymethyl)-5-(3-hydroxypropyl)benzofuran-7-ol	Generator

Chemical Formula

C₂₅H₃₂O₁₀

Average Mass

492.5210 Da

Monoisotopic Mass

492.19955 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)[C@@H]1OC2=C(O)C=C(CCCO)C=C2[C@@H]1CO

InChI Identifier

InChI=1S/C25H32O10/c1-12-20(29)21(30)22(31)25(33-12)34-18-6-5-14(10-19(18)32-2)23-16(11-27)15-8-13(4-3-7-26)9-17(28)24(15)35-23/h5-6,8-10,12,16,20-23,25-31H,3-4,7,11H2,1-2H3/t12-,16-,20-,21+,22+,23-,25-/m0/s1

InChI Key

PHHIEOZUONPPQY-QDCFJCCASA-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
Picea abies	LOTUS Database	35616633
Pinus massoniana	LOTUS Database	35616633
Pinus sibirica	LOTUS Database	35616633
Pinus sylvestris	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
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Ether
Acetal
Polyol
Oxacycle
Organic oxygen compound
Alcohol
Primary alcohol
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

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

101992984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol (NP0160164)

MOL for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D MOL for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D SDF for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D-SDF for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

PDB for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D PDB for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

SMILES for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

INCHI for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

Structure for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)

3D Structure for NP0160164 ((2s,3r,4r,5r,6s)-2-{4-[(2r,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-methyloxane-3,4,5-triol)