NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate (NP0159981)

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Record Information

Version

2.0

Created at

2022-09-02 17:50:07 UTC

Updated at

2022-09-02 17:50:07 UTC

NP-MRD ID

NP0159981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate

Description

(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. (2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate is found in Senecio mairetianus. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219502D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022219502D          

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M  END
> <DATABASE_ID>
NP0159981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](OC(C)=O)[C@@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O13/c1-9(26)34-24-20(32)22(18(30)16(8-25)36-24)37-23-19(31)17-13(29)6-11(27)7-15(17)35-21(23)10-3-4-12(28)14(5-10)33-2/h3-7,16,18,20,22,24-25,27-30,32H,8H2,1-2H3/t16-,18-,20-,22+,24-/m1/s1

> <INCHI_KEY>
TZCCUAFGXBAIAM-YEEBRUQLSA-N

> <FORMULA>
C24H24O13

> <MOLECULAR_WEIGHT>
520.443

> <EXACT_MASS>
520.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.27595596186947

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
0.4421841703333339

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.938033709164952

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.378426485668743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811120463768734

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
122.9093

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.865  -5.551   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   20   33                                                  
CONECT   33   32                                                            
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₃

Average Mass

520.4430 Da

Monoisotopic Mass

520.12169 Da

IUPAC Name

(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate

Traditional Name

(2S,3R,4S,5R,6R)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](OC(C)=O)[C@@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C24H24O13/c1-9(26)34-24-20(32)22(18(30)16(8-25)36-24)37-23-19(31)17-13(29)6-11(27)7-15(17)35-21(23)10-3-4-12(28)14(5-10)33-2/h3-7,16,18,20,22,24-25,27-30,32H,8H2,1-2H3/t16-,18-,20-,22+,24-/m1/s1

InChI Key

TZCCUAFGXBAIAM-YEEBRUQLSA-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
Senecio mairetianus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hexose monosaccharide
Chromone
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Acetal
Ether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	1.47	ALOGPS
logP	0.44	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.91 m³·mol⁻¹	ChemAxon
Polarizability	49.28 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

163056082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate (NP0159981)

MOL for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

3D MOL for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

3D SDF for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

3D-SDF for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

PDB for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

3D PDB for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

SMILES for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

INCHI for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

Structure for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)

3D Structure for NP0159981 ((2s,3r,4s,5r,6r)-4-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl acetate)