NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate (NP0318551)

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Record Information

Version

2.0

Created at

2022-09-11 19:06:59 UTC

Updated at

2022-09-11 19:06:59 UTC

NP-MRD ID

NP0318551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate

Description

(3R)-3alpha-Methyl-6-[6-O-(4-methoxybenzoyl)-beta-D-glucopyranosyloxy]-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on (3R)-3alpha-Methyl-6-[6-O-(4-methoxybenzoyl)-beta-D-glucopyranosyloxy]-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221072D          

 35 38  0  0  1  0            999 V2000
   -8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112221072D          

 35 38  0  0  1  0            999 V2000
   -8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0318551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)O[C@H](C)CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O11/c1-11-7-13-8-15(9-16(25)18(13)23(30)33-11)34-24-21(28)20(27)19(26)17(35-24)10-32-22(29)12-3-5-14(31-2)6-4-12/h3-6,8-9,11,17,19-21,24-28H,7,10H2,1-2H3/t11-,17-,19-,20+,21-,24-/m1/s1

> <INCHI_KEY>
KPDZBOPXDVHHMX-MZXLOQKJSA-N

> <FORMULA>
C24H26O11

> <MOLECULAR_WEIGHT>
490.461

> <EXACT_MASS>
490.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.09856336347949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate

> <JCHEM_LOGP>
2.345616157333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202494723352814

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.504593162399376

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110481367919

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
118.20310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0     -16.004  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -16.004  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -14.670  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26                                                            
CONECT   28   13   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   11   33                                                  
CONECT   33   32                                                            
CONECT   34    6   35                                                       
CONECT   35   34    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3a-Methyl-6-[6-O-(4-methoxybenzoyl)-b-D-glucopyranosyloxy]-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one	Generator
(3R)-3Α-methyl-6-[6-O-(4-methoxybenzoyl)-β-D-glucopyranosyloxy]-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one	Generator

Chemical Formula

C₂₄H₂₆O₁₁

Average Mass

490.4610 Da

Monoisotopic Mass

490.14751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)O[C@H](C)CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C24H26O11/c1-11-7-13-8-15(9-16(25)18(13)23(30)33-11)34-24-21(28)20(27)19(26)17(35-24)10-32-22(29)12-3-5-14(31-2)6-4-12/h3-6,8-9,11,17,19-21,24-28H,7,10H2,1-2H3/t11-,17-,19-,20+,21-,24-/m1/s1

InChI Key

KPDZBOPXDVHHMX-MZXLOQKJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
P-methoxybenzoic acid or derivatives
Benzoate ester
Benzopyran
Isochromane
2-benzopyran
Benzoic acid or derivatives
Benzoyl
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxide
Alcohol
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

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

9830843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11656105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate (NP0318551)

MOL for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

3D MOL for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

3D SDF for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

3D-SDF for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

PDB for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

3D PDB for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

SMILES for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

INCHI for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

Structure for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)

3D Structure for NP0318551 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate)