NP-MRD: Showing NP-Card for (2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol (NP0328147)

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Record Information

Version

2.0

Created at

2022-09-12 11:21:31 UTC

Updated at

2022-09-12 11:21:31 UTC

NP-MRD ID

NP0328147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL3088137 belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol is found in Abies holophylla. Based on a literature review very few articles have been published on CHEMBL3088137.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213212D          

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M  END

     RDKit          3D

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  Mrv1652309122213212D          

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  5 22  2  0  0  0  0
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 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0328147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](OC2=CC=C(C=C2OC)[C@@H]2OC3=C(O)C=C(CCCO)C=C3[C@H]2CO)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-13-21(30)25(33-3)22(31)26(34-13)35-19-7-6-15(11-20(19)32-2)23-17(12-28)16-9-14(5-4-8-27)10-18(29)24(16)36-23/h6-7,9-11,13,17,21-23,25-31H,4-5,8,12H2,1-3H3/t13-,17+,21-,22+,23-,25+,26-/m0/s1

> <INCHI_KEY>
BRHGOUNQMOKXSV-OHDBAMMWSA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.752353539632715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.2326007513333341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.284942511919036

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.980631749184793

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416081814137

> <JCHEM_POLAR_SURFACE_AREA>
147.3

> <JCHEM_REFRACTIVITY>
128.3639

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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     -10.330   0.031   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.250   0.031   0.000  0.00  0.00           C+0
HETATM   36  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   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   26   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](OC2=CC=C(C=C2OC)[C@@H]2OC3=C(O)C=C(CCCO)C=C3[C@H]2CO)[C@@H]1O

InChI Identifier

InChI=1S/C26H34O10/c1-13-21(30)25(33-3)22(31)26(34-13)35-19-7-6-15(11-20(19)32-2)23-17(12-28)16-9-14(5-4-8-27)10-18(29)24(16)36-23/h6-7,9-11,13,17,21-23,25-31H,4-5,8,12H2,1-3H3/t13-,17+,21-,22+,23-,25+,26-/m0/s1

InChI Key

BRHGOUNQMOKXSV-OHDBAMMWSA-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
Abies holophylla	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
Dialkyl ether
Acetal
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
logP	1.23	ChemAxon
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.36 m³·mol⁻¹	ChemAxon
Polarizability	53.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

31144870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72948049

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,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol (NP0328147)

MOL for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

3D MOL for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

3D SDF for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

3D-SDF for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

PDB for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

3D PDB for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

SMILES for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

INCHI for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

Structure for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)

3D Structure for NP0328147 ((2s,3r,4r,5s,6s)-2-{4-[(2r,3s)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-4-methoxy-6-methyloxane-3,5-diol)