NP-MRD: Showing NP-Card for 4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate (NP0318694)

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Record Information

Version

2.0

Created at

2022-09-11 19:20:24 UTC

Updated at

2022-09-11 19:20:24 UTC

NP-MRD ID

NP0318694

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate

Description

4,5-Bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}oxan-3-yl acetate belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position. 4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate is found in Rhodiola algida. 4,5-Bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}oxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520472D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231520472D          

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 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 16 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 19 30  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
  5 36  1  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
M  END
> <DATABASE_ID>
NP0318694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1COC(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C=C2)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O14/c1-10(27)36-17-9-35-26(25(38-12(3)29)23(17)37-11(2)28)40-22-16(32)8-15(31)18-19(33)20(34)21(39-24(18)22)13-4-6-14(30)7-5-13/h4-8,17,23,25-26,30-32,34H,9H2,1-3H3

> <INCHI_KEY>
UUUFLHFLFWPUFF-UHFFFAOYSA-N

> <FORMULA>
C26H24O14

> <MOLECULAR_WEIGHT>
560.464

> <EXACT_MASS>
560.116605453

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.96974415617351

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}oxan-3-yl acetate

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
1.8419425436666659

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.115952418810952

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.762703097220963

> <JCHEM_PKA_STRONGEST_BASIC>
-3.956766710254896

> <JCHEM_POLAR_SURFACE_AREA>
204.57999999999998

> <JCHEM_REFRACTIVITY>
130.49859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.334 -11.550   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   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   10   16                                                  
CONECT   23   20   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   19                                                            
CONECT   31    8   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31    5   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
4,5-Bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₆H₂₄O₁₄

Average Mass

560.4640 Da

Monoisotopic Mass

560.11661 Da

IUPAC Name

4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}oxan-3-yl acetate

Traditional Name

4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1COC(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C=C2)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C26H24O14/c1-10(27)36-17-9-35-26(25(38-12(3)29)23(17)37-11(2)28)40-22-16(32)8-15(31)18-19(33)20(34)21(39-24(18)22)13-4-6-14(30)7-5-13/h4-8,17,23,25-26,30-32,34H,9H2,1-3H3

InChI Key

UUUFLHFLFWPUFF-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

Species Name	Source	Reference
Rhodiola algida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glycosides

Alternative Parents

Substituents

Flavonoid-8-o-glycoside
3-hydroxyflavone
Flavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Tricarboxylic acid or derivatives
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	2.48	ALOGPS
logP	1.84	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	204.58 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.5 m³·mol⁻¹	ChemAxon
Polarizability	52.97 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

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-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate (NP0318694)

MOL for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

PDB for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

SMILES for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

INCHI for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

Structure for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0318694 (4,5-bis(acetyloxy)-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)