NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0183247)

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Record Information

Version

2.0

Created at

2022-09-03 22:07:32 UTC

Updated at

2022-09-03 22:07:32 UTC

NP-MRD ID

NP0183247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Description

2-(4-Hydroxyphenyl)-3,5-dihydroxy-7-(6-O-acetyl-beta-D-glucopyranosyloxy)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Based on a literature review very few articles have been published on 2-(4-Hydroxyphenyl)-3,5-dihydroxy-7-(6-O-acetyl-beta-D-glucopyranosyloxy)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200072D          

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M  END

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  Mrv1652309042200072D          

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   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  2  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0183247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(=C(O)C(=O)C2=C(O)C=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O12/c1-12(2)4-9-16-18(38-28-25(36)23(34)21(32)19(39-28)11-37-13(3)29)10-17(31)20-22(33)24(35)26(40-27(16)20)14-5-7-15(30)8-6-14/h4-8,10,19,21,23,25,28,30-32,34-36H,9,11H2,1-3H3/t19-,21-,23+,25-,28-/m1/s1

> <INCHI_KEY>
PUSFLQDHYYXEKU-RLEYFDEBSA-N

> <FORMULA>
C28H30O12

> <MOLECULAR_WEIGHT>
558.536

> <EXACT_MASS>
558.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
56.02403908591794

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_LOGP>
2.3614891019999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.510482931251

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.057591969711952

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028170838513

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
140.42000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -3.080   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   28                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   19   28                                                       
CONECT   28   27   14   29                                                  
CONECT   29   28   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    8   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    6   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
2-(4-Hydroxyphenyl)-3,5-dihydroxy-7-(6-O-acetyl-b-D-glucopyranosyloxy)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	Generator
2-(4-Hydroxyphenyl)-3,5-dihydroxy-7-(6-O-acetyl-β-D-glucopyranosyloxy)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	Generator

Chemical Formula

C₂₈H₃₀O₁₂

Average Mass

558.5360 Da

Monoisotopic Mass

558.17373 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(=C(O)C(=O)C2=C(O)C=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C28H30O12/c1-12(2)4-9-16-18(38-28-25(36)23(34)21(32)19(39-28)11-37-13(3)29)10-17(31)20-22(33)24(35)26(40-27(16)20)14-5-7-15(30)8-6-14/h4-8,10,19,21,23,25,28,30-32,34-36H,9,11H2,1-3H3/t19-,21-,23+,25-,28-/m1/s1

InChI Key

PUSFLQDHYYXEKU-RLEYFDEBSA-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 flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
8-prenylated flavone
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
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

9881441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11706718

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)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0183247)

MOL for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

PDB for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

SMILES for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

INCHI for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

Structure for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0183247 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)