NP-MRD: Showing NP-Card for (2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol (NP0247555)

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Record Information

Version

2.0

Created at

2022-09-07 09:26:55 UTC

Updated at

2022-09-07 09:26:55 UTC

NP-MRD ID

NP0247555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211262D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072211262D          

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   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
  5 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@@H]([C@@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C2=CC(CCCO)=C1)C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O11/c1-13-21(29)23(31)24(32)27(37-13)36-12-17-16-8-14(6-5-7-28)9-20(35-4)26(16)38-25(17)15-10-18(33-2)22(30)19(11-15)34-3/h8-11,13,17,21,23-25,27-32H,5-7,12H2,1-4H3/t13-,17-,21-,23+,24+,25+,27+/m0/s1

> <INCHI_KEY>
DAPCPLQFHONFRT-NKMYOPCVSA-N

> <FORMULA>
C27H36O11

> <MOLECULAR_WEIGHT>
536.574

> <EXACT_MASS>
536.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.3979396827946

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.074929485666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.225164811798185

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30164579496982

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416082336521

> <JCHEM_POLAR_SURFACE_AREA>
156.53

> <JCHEM_REFRACTIVITY>
134.8271

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.940   1.365   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   2.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.592  -2.073   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.253  -9.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.760 -10.192   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.821  -7.903   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23   32                                                  
CONECT   32   31                                                            
CONECT   33    5   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₁₁

Average Mass

536.5740 Da

Monoisotopic Mass

536.22576 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@@H]([C@@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C2=CC(CCCO)=C1)C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C27H36O11/c1-13-21(29)23(31)24(32)27(37-13)36-12-17-16-8-14(6-5-7-28)9-20(35-4)26(16)38-25(17)15-10-18(33-2)22(30)19(11-15)34-3/h8-11,13,17,21,23-25,27-32H,5-7,12H2,1-4H3/t13-,17-,21-,23+,24+,25+,27+/m0/s1

InChI Key

DAPCPLQFHONFRT-NKMYOPCVSA-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
Chaenomeles sinensis	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
Dimethoxybenzene
Methoxyphenol
M-dimethoxybenzene
Benzofuran
Coumaran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
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	1.07	ChemAxon
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.83 m³·mol⁻¹	ChemAxon
Polarizability	56.4 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58859132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122179010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol (NP0247555)

MOL for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

3D MOL for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

3D SDF for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

3D-SDF for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

PDB for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

3D PDB for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

SMILES for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

INCHI for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

Structure for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)

3D Structure for NP0247555 ((2r,3r,4r,5r,6s)-2-{[(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy}-6-methyloxane-3,4,5-triol)