NP-MRD: Showing NP-Card for 7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one (NP0060222)

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Record Information

Version

1.0

Created at

2022-04-28 05:18:56 UTC

Updated at

2022-04-28 05:18:56 UTC

NP-MRD ID

NP0060222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one

Description

7-{[(2R,3R,4R,5S,6S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one is found in Halocnemum strobilaceum . Based on a literature review very few articles have been published on 7-{[(2R,3R,4R,5S,6S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207182D          

 34 37  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 34  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282207182D          

 34 37  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0060222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O[C@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3N)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23NO11/c1-31-12-4-8(2-3-10(12)25)21-20(30)18(28)15-11(26)5-9(6-13(15)33-21)32-22-16(23)19(29)17(27)14(7-24)34-22/h2-6,14,16-17,19,22,24-27,29-30H,7,23H2,1H3/t14-,16+,17+,19+,22-/m0/s1

> <INCHI_KEY>
PDOICZRLIROUNN-LHVWXBTBSA-N

> <FORMULA>
C22H23NO11

> <MOLECULAR_WEIGHT>
477.422

> <EXACT_MASS>
477.127110565

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.51050521870983

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.9305390693398176

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.817944455024998

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.007937267452938

> <JCHEM_PKA_STRONGEST_BASIC>
7.806966735694522

> <JCHEM_POLAR_SURFACE_AREA>
201.39

> <JCHEM_REFRACTIVITY>
115.14639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.40e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    2   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   12                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   26                                                            
CONECT   32   25                                                            
CONECT   33   24                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃NO₁₁

Average Mass

477.4220 Da

Monoisotopic Mass

477.12711 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O[C@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3N)C=C2O1

InChI Identifier

InChI=1S/C22H23NO11/c1-31-12-4-8(2-3-10(12)25)21-20(30)18(28)15-11(26)5-9(6-13(15)33-21)32-22-16(23)19(29)17(27)14(7-24)34-22/h2-6,14,16-17,19,22,24-27,29-30H,7,23H2,1H3/t14-,16+,17+,19+,22-/m0/s1

InChI Key

PDOICZRLIROUNN-LHVWXBTBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Halocnemum strobilaceum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Aminoglycoside core
3-hydroxyflavone
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
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	0.52	ALOGPS
logP	-0.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.01	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	201.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.15 m³·mol⁻¹	ChemAxon
Polarizability	46.51 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	No	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

163082162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one (NP0060222)

MOL for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D MOL for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D SDF for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D-SDF for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

PDB for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D PDB for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

SMILES for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

INCHI for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

Structure for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D Structure for NP0060222 (7-[(2-Amino-2-deoxy-alpha-D-glucopyranosyl)oxy]-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)