NP-MRD: Showing NP-Card for 4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate (NP0163791)

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Record Information

Version

2.0

Created at

2022-09-02 22:32:09 UTC

Updated at

2022-09-02 22:32:09 UTC

NP-MRD ID

NP0163791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-(Acetyloxy)-5-hydroxy-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-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate is found in Rhodiola algida. 4-(Acetyloxy)-5-hydroxy-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


  Mrv1533004181503462D          

 37 40  0  0  0  0            999 V2000
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   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   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
    0.0000   -2.4750    0.0000 O   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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 35 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004181503462D          

 37 40  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0163791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)COC(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C=C2)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O13/c1-9(25)34-21-15(30)8-33-24(23(21)35-10(2)26)37-20-14(29)7-13(28)16-17(31)18(32)19(36-22(16)20)11-3-5-12(27)6-4-11/h3-7,15,21,23-24,27-30,32H,8H2,1-2H3

> <INCHI_KEY>
XISTWCWMRYYNJX-UHFFFAOYSA-N

> <FORMULA>
C24H22O13

> <MOLECULAR_WEIGHT>
518.427

> <EXACT_MASS>
518.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.50939507501213

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.400817133333334

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.115949722926148

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.762703001363498

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5421079363998533

> <JCHEM_POLAR_SURFACE_AREA>
198.50999999999996

> <JCHEM_REFRACTIVITY>
121.3471

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.48e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -7.700   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       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -3.080   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.335  -7.700   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   33                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   32                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   12   18                                                  
CONECT   25   22   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   21                                                            
CONECT   33   10    5   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₄H₂₂O₁₃

Average Mass

518.4270 Da

Monoisotopic Mass

518.10604 Da

IUPAC Name

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

Traditional Name

4-(acetyloxy)-5-hydroxy-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)OC1C(O)COC(OC2=C(O)C=C(O)C3=C2OC(=C(O)C3=O)C2=CC=C(O)C=C2)C1OC(C)=O

InChI Identifier

InChI=1S/C24H22O13/c1-9(25)34-21-15(30)8-33-24(23(21)35-10(2)26)37-20-14(29)7-13(28)16-17(31)18(32)19(36-22(16)20)11-3-5-12(27)6-4-11/h3-7,15,21,23-24,27-30,32H,8H2,1-2H3

InChI Key

XISTWCWMRYYNJX-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
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Benzenoid
Monosaccharide
Pyran
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Acetal
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	2.31	ALOGPS
logP	1.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.35 m³·mol⁻¹	ChemAxon
Polarizability	48.51 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

74978531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate (NP0163791)

MOL for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

PDB for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

SMILES for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

INCHI for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

Structure for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0163791 (4-(acetyloxy)-5-hydroxy-2-{[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}oxan-3-yl acetate)