NP-MRD: Showing NP-Card for 4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate (NP0330655)

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Record Information

Version

2.0

Created at

2022-09-12 16:12:53 UTC

Updated at

2022-09-12 16:12:53 UTC

NP-MRD ID

NP0330655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate

Description

4-{5,7-Dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetate belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Based on a literature review very few articles have been published on 4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218122D          

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M  END

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M  END


  Mrv1652309122218122D          

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    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 19 39  2  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  0  0  0  0
  9 40  1  0  0  0  0
  8 41  1  0  0  0  0
 41 42  2  0  0  0  0
  5 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330655

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H28O13/c1-12-25(39-14(3)31)28(40-15(4)32)29(41-16(5)33)27(37-12)24-20(35)10-19(34)23-21(36)11-22(42-26(23)24)17-6-8-18(9-7-17)38-13(2)30/h6-12,25,27-29,34-35H,1-5H3/t12-,25-,27+,28+,29+/m1/s1

> <INCHI_KEY>
OFJRVBXBHBGOTA-PTUVCELYSA-N

> <FORMULA>
C29H28O13

> <MOLECULAR_WEIGHT>
584.53

> <EXACT_MASS>
584.152990962

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.56099476434467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetate

> <JCHEM_LOGP>
2.2304807223333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.090691669105288

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1737197928114345

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204881324509189

> <JCHEM_POLAR_SURFACE_AREA>
181.18999999999997

> <JCHEM_REFRACTIVITY>
141.0945

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate

> <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      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   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  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   42                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   41                                                  
CONECT    9    8   10   40                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   39                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   39                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   20   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   19   13   40                                                  
CONECT   40   39    9                                                       
CONECT   41    8   42                                                       
CONECT   42   41    5                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetic acid	Generator

Chemical Formula

C₂₉H₂₈O₁₃

Average Mass

584.5300 Da

Monoisotopic Mass

584.15299 Da

IUPAC Name

4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetate

Traditional Name

4-{5,7-dihydroxy-4-oxo-8-[(2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H28O13/c1-12-25(39-14(3)31)28(40-15(4)32)29(41-16(5)33)27(37-12)24-20(35)10-19(34)23-21(36)11-22(42-26(23)24)17-6-8-18(9-7-17)38-13(2)30/h6-12,25,27-29,34-35H,1-5H3/t12-,25-,27+,28+,29+/m1/s1

InChI Key

OFJRVBXBHBGOTA-PTUVCELYSA-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 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Tetracarboxylic acid or derivatives
Chromone
Benzopyran
Phenol ester
1-benzopyran
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	2.23	ChemAxon
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	181.19 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.09 m³·mol⁻¹	ChemAxon
Polarizability	57.56 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

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

162876310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate (NP0330655)

MOL for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D MOL for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D SDF for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D-SDF for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

PDB for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D PDB for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

SMILES for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

INCHI for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

Structure for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D Structure for NP0330655 (4-{5,7-dihydroxy-4-oxo-8-[(2s,3s,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)