NP-MRD: Showing NP-Card for 3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate (NP0301313)

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Record Information

Version

2.0

Created at

2022-09-10 14:10:59 UTC

Updated at

2022-09-10 14:11:00 UTC

NP-MRD ID

NP0301313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

Description

Myricetin 3-(3'',4''-diacetylrhamnoside) belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Myricetin 3-(3'',4''-diacetylrhamnoside) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Myricetin 3-(3'',4''-diacetylrhamnoside) has been detected, but not quantified in, fruits. 3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate is found in Myrsine africana. This could make myricetin 3-(3'',4''-diacetylrhamnoside) a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209382D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241209382D          

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 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  0  0  0  0
 26 27  1  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 37  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O14/c1-8-21(36-9(2)26)24(37-10(3)27)20(34)25(35-8)39-23-19(33)17-13(29)6-12(28)7-16(17)38-22(23)11-4-14(30)18(32)15(31)5-11/h4-8,20-21,24-25,28-32,34H,1-3H3

> <INCHI_KEY>
HIVURPVQOPPNFN-UHFFFAOYSA-N

> <FORMULA>
C25H24O14

> <MOLECULAR_WEIGHT>
548.4497

> <EXACT_MASS>
548.116605476

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
51.1779338789045

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
1.4807601696666672

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.077441754872993

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.428092744249556

> <JCHEM_PKA_STRONGEST_BASIC>
-3.969602256786499

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999995

> <JCHEM_REFRACTIVITY>
128.01569999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.331  -0.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   0.771   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334  -3.849   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -3.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.331  -3.846   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.665  -3.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.999  -3.846   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.330  -3.077   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.665  -1.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.999  -0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.333  -1.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.333  -3.077   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.999  -3.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.665  -3.077   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.999   0.771   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.330  -6.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.999  -5.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.665  -6.155   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.331  -5.386   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.665  -7.694   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.664  -3.846   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.331   0.768   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.665   1.538   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.665   3.079   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.331   3.849   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   3.079   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.000   1.538   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334   3.849   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.331   5.386   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.999   3.849   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.999   0.771   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.330   3.077   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.330   1.538   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.664   3.846   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.665   6.158   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.665   7.694   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.999   5.388   0.000  0.00  0.00           C+0
CONECT    1    2   24                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3                                                            
CONECT    5    6   16                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9                                                            
CONECT   11    3   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16    5   11   15                                                  
CONECT   17   12                                                            
CONECT   18   19                                                            
CONECT   19    9   18   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21    7   20                                                       
CONECT   22   20                                                            
CONECT   23   14                                                            
CONECT   24    1   25   29                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   24   28                                                       
CONECT   30   28                                                            
CONECT   31   27   37                                                       
CONECT   32   26   34                                                       
CONECT   33   25                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   31   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
3-[(3,4-Di-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one	HMDB
3-(Acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₂₄O₁₄

Average Mass

548.4497 Da

Monoisotopic Mass

548.11661 Da

IUPAC Name

3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

Traditional Name

3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C25H24O14/c1-8-21(36-9(2)26)24(37-10(3)27)20(34)25(35-8)39-23-19(33)17-13(29)6-12(28)7-16(17)38-22(23)11-4-14(30)18(32)15(31)5-11/h4-8,20-21,24-25,28-32,34H,1-3H3

InChI Key

HIVURPVQOPPNFN-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
Myrsine africana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Benzenetriol
Pyrogallol derivative
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Pyran
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
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	2.99	ALOGPS
logP	1.48	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.02 m³·mol⁻¹	ChemAxon
Polarizability	51.18 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

HMDB0029877

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001107

KNApSAcK ID

C00013976

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

74978317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate (NP0301313)

MOL for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D MOL for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D SDF for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D-SDF for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

PDB for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D PDB for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

SMILES for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

INCHI for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

Structure for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)

3D Structure for NP0301313 (3-(acetyloxy)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-5-hydroxy-2-methyloxan-4-yl acetate)