NP-MRD: Showing NP-Card for Vitexin-2''-O-rhamnoside (NP0137372)

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Record Information

Version

2.0

Created at

2022-05-30 16:50:33 UTC

Updated at

2022-05-30 16:50:33 UTC

NP-MRD ID

NP0137372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vitexin-2''-O-rhamnoside

Description

Vitexin-2''-O-rhamnoside is found in Celtis australis, Citrus japonica, Cotoneaster orbicularis, Dacrycarpus dacrydioides, Glycine max, Machilus japonica, Podocarpus totara and Turnera diffusa.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241221572D          

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M  END

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  Mrv0541 02241221572D          

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  2  3  2  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 22 38  1  0  0  0  0
 23 30  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 39  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 31  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 41  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)C(CO)OC2C2=C3OC(=CC(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3

> <INCHI_KEY>
LYGPBZVKGHHTIE-UHFFFAOYSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.5187

> <EXACT_MASS>
578.163555668

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
56.245026930532575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.7745574503333336

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.6150822579845

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.198726967834775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826114733837

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
136.90179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-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      -3.333   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.001   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.666   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.666   5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.337   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.337  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.670  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.670   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.669  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.001   5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.335   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.001   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.668   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.668   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.666   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.666  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.333  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.668  -1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.668  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.001  -3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.001  -5.390   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.000   0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.000  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.668  -1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.668  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.669  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -7.335  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.000  -3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.000  -5.390   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.333  -3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.001  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.666  -3.850   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.666  -5.390   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -8.669  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    6   10                                                       
CONECT   12    7                                                            
CONECT   13   14                                                            
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   10   15   17                                                  
CONECT   17   16   19                                                       
CONECT   18    4   14   19                                                  
CONECT   19   17   18   20                                                  
CONECT   20    2   19   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23   38                                                  
CONECT   23   22   30                                                       
CONECT   24   21   25                                                       
CONECT   25   24   26   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   28   30   33                                                  
CONECT   30   23   29   31                                                  
CONECT   31   30   35                                                       
CONECT   32   33                                                            
CONECT   33   29   32   34                                                  
CONECT   34   33   35   41                                                  
CONECT   35   31   34   36                                                  
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   22   37   39                                                  
CONECT   39   25   38   40                                                  
CONECT   40   39                                                            
CONECT   41   34                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Vitexin rhamnoside	MeSH
Vitexin-2''-O-rhamnoside	MeSH
8-Glycosyl-apigenin-rhamnoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5187 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

8-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2C2=C3OC(=CC(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3

InChI Key

LYGPBZVKGHHTIE-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
Celtis australis	LOTUS Database	35616633
Citrus japonica	LOTUS Database	35616633
Cotoneaster orbicularis	LOTUS Database	35616633
Dacrycarpus dacrydioides	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Machilus japonica	LOTUS Database	35616633
Podocarpus totara	LOTUS Database	35616633
Turnera diffusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
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	-0.1	ALOGPS
logP	-0.77	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.9 m³·mol⁻¹	ChemAxon
Polarizability	56.25 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021638

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

5874704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vitexin-2''-O-rhamnoside (NP0137372)

MOL for NP0137372 (Vitexin-2''-O-rhamnoside)

3D MOL for NP0137372 (Vitexin-2''-O-rhamnoside)

3D SDF for NP0137372 (Vitexin-2''-O-rhamnoside)

3D-SDF for NP0137372 (Vitexin-2''-O-rhamnoside)

PDB for NP0137372 (Vitexin-2''-O-rhamnoside)

3D PDB for NP0137372 (Vitexin-2''-O-rhamnoside)

SMILES for NP0137372 (Vitexin-2''-O-rhamnoside)

INCHI for NP0137372 (Vitexin-2''-O-rhamnoside)

Structure for NP0137372 (Vitexin-2''-O-rhamnoside)

3D Structure for NP0137372 (Vitexin-2''-O-rhamnoside)