NP-MRD: Showing NP-Card for Isovitexin 2''-glucoside (NP0045389)

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Record Information

Version

2.0

Created at

2022-03-17 19:19:07 UTC

Updated at

2022-03-17 19:19:07 UTC

NP-MRD ID

NP0045389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovitexin 2''-glucoside

Description

Isovitexin 2''-O-glucoside, also known as meloside a, belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isovitexin 2''-O-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isovitexin 2''-O-glucoside has been detected, but not quantified in, a few different foods, such as cucumbers, muskmelons, and tea. Isovitexin 2''-glucoside is found in Camellia sinensis , Centaurea triumfetti, Clutia abyssinica , Oxalis acetosella , Passiflora incarnata , Secale cereale and Ziziphus jujuba . This could make isovitexin 2''-O-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217332D          

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 41 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02241217332D          

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   -2.5005    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    3.7126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  2 32  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 27  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 15 29  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 33  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 39  1  0  0  0  0
 20 21  1  0  0  0  0
 20 36  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 40  1  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045389

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2C(O)C(O)C(CO)OC2C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2

> <INCHI_KEY>
RQTTXGQDIROLTQ-UHFFFAOYSA-N

> <FORMULA>
C27H30O15

> <MOLECULAR_WEIGHT>
594.5181

> <EXACT_MASS>
594.15847029

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
57.69775702898954

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.67

> <JCHEM_LOGP>
-1.821467417

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.50206612280177

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.196596382383968

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645025606539847

> <JCHEM_POLAR_SURFACE_AREA>
256.28999999999996

> <JCHEM_REFRACTIVITY>
138.44549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <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      -4.668  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.669  -1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.002  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.670  -6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.670  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.337  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.337  -6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.669  -6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.001   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.333  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.998  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.998  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.333  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.333   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.998   0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.998   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.666   3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.668   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.666  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.668  -3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.001  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.335  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.335  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.666  -1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.666   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -7.334   0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.668   0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.668   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.668   5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.666   4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.998   5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.333   4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.333   3.080   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.998   6.930   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.668   5.390   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10                                                            
CONECT   12   27                                                            
CONECT   13   14                                                            
CONECT   14   13   15   22                                                  
CONECT   15   14   16   29                                                  
CONECT   16    1   15   17                                                  
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   39                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20                                                            
CONECT   22   14   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25    7   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   12   26   28                                                  
CONECT   28   23   27   29                                                  
CONECT   29   15   28   30                                                  
CONECT   30   29                                                            
CONECT   31   32                                                            
CONECT   32    2   31   33                                                  
CONECT   33   17   32   34                                                  
CONECT   34   33                                                            
CONECT   35   36                                                            
CONECT   36   20   35   37                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39   41                                                  
CONECT   39   19   38                                                       
CONECT   40   37                                                            
CONECT   41   38   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Meloside a	HMDB
Isovitexin 2''-O-beta-glucoside	MeSH
Isovitexin 2''-O-glucoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₅

Average Mass

594.5181 Da

Monoisotopic Mass

594.15847 Da

IUPAC Name

6-[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

6-[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

60767-80-8

SMILES

OCC1OC(OC2C(O)C(O)C(CO)OC2C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2

InChI Key

RQTTXGQDIROLTQ-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, 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
Camellia sinensis	Plant	KNApSAcK
Centaurea triumfetti	Plant	KNApSAcK
Clutia abyssinica	Plant	KNApSAcK
Cucumis melo	FooDB	KNAPSACK
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oxalis acetosella	Plant	KNApSAcK
Passiflora incarnata	Plant	KNApSAcK
Secale cereale	Plant	KNApSAcK
Ziziphus jujuba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
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	-0.67	ALOGPS
logP	-1.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.45 m³·mol⁻¹	ChemAxon
Polarizability	57.7 Å³	ChemAxon
Number of Rings	5	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

HMDB0029484

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000615

KNApSAcK ID

C00006219

Chemspider ID

286921

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

323971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isovitexin 2''-glucoside (NP0045389)

MOL for NP0045389 (Isovitexin 2''-glucoside)

3D MOL for NP0045389 (Isovitexin 2''-glucoside)

3D SDF for NP0045389 (Isovitexin 2''-glucoside)

3D-SDF for NP0045389 (Isovitexin 2''-glucoside)

PDB for NP0045389 (Isovitexin 2''-glucoside)

3D PDB for NP0045389 (Isovitexin 2''-glucoside)

SMILES for NP0045389 (Isovitexin 2''-glucoside)

INCHI for NP0045389 (Isovitexin 2''-glucoside)

Structure for NP0045389 (Isovitexin 2''-glucoside)

3D Structure for NP0045389 (Isovitexin 2''-glucoside)