NP-MRD: Showing NP-Card for 4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate (NP0283159)

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Record Information

Version

2.0

Created at

2022-09-09 10:18:06 UTC

Updated at

2022-09-09 10:18:07 UTC

NP-MRD ID

NP0283159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-{5,7-Dihydroxy-4-oxo-8-[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. 4-{5,7-Dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]-4H-chromen-2-yl}phenyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517132D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241517132D          

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    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   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
    4.2868   -2.4750    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
 26 32  2  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 33 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)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

> <INCHI_KEY>
OFJRVBXBHBGOTA-UHFFFAOYSA-N

> <FORMULA>
C29H28O13

> <MOLECULAR_WEIGHT>
584.53

> <EXACT_MASS>
584.152990962

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
56.37753484589121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.2304807223333327

> <ALOGPS_LOGS>
-4.11

> <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>
141.09449999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-2-{2-[4-(acetyloxy)phenyl]-5,7-dihydroxy-4-oxochromen-8-yl}-6-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    4   21   32                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   20   26                                                  
CONECT   33   30   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   42                                                       
CONECT   42   41   33                                                       
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-[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-bis(acetyloxy)-2-{2-[4-(acetyloxy)phenyl]-5,7-dihydroxy-4-oxo-4H-chromen-8-yl}-6-methyloxan-3-yl acetate

Traditional Name

4,5-bis(acetyloxy)-2-{2-[4-(acetyloxy)phenyl]-5,7-dihydroxy-4-oxochromen-8-yl}-6-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)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

InChI Key

OFJRVBXBHBGOTA-UHFFFAOYSA-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	3.37	ALOGPS
logP	2.23	ChemAxon
logS	-4.1	ALOGPS
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	56.38 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

Not Available

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-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate (NP0283159)

MOL for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D MOL for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D SDF for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D-SDF for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

PDB for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D PDB for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

SMILES for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

INCHI for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

Structure for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)

3D Structure for NP0283159 (4-{5,7-dihydroxy-4-oxo-8-[3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]chromen-2-yl}phenyl acetate)