NP-MRD: Showing NP-Card for 2'',6''-Di-O-Acetyl isovitexin (NP0060353)

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Record Information

Version

2.0

Created at

2022-04-28 05:25:29 UTC

Updated at

2022-04-28 05:25:29 UTC

NP-MRD ID

NP0060353

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'',6''-Di-O-Acetyl isovitexin

Description

2'',6''-Di-o-acetyl isovitexin 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. Thus, 2'',6''-di-O-acetyl isovitexin is considered to be a flavonoid. 2'',6''-Di-O-Acetyl isovitexin is found in Crotalaria thebaica. Based on a literature review very few articles have been published on 2'',6''-di-o-acetyl isovitexin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207252D          

 37 40  0  0  1  0            999 V2000
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    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282207252D          

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M  END
> <DATABASE_ID>
NP0060353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c1-10(26)34-9-18-21(31)23(33)25(35-11(2)27)24(37-18)20-15(30)8-17-19(22(20)32)14(29)7-16(36-17)12-3-5-13(28)6-4-12/h3-8,18,21,23-25,28,30-33H,9H2,1-2H3/t18-,21-,23+,24+,25-/m1/s1

> <INCHI_KEY>
KMFYISKCEINRIB-WIOLZNRFSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
51.05785801311363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
0.8316190493333329

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.7121931719813395

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.137407052372193

> <JCHEM_PKA_STRONGEST_BASIC>
-3.646155253134829

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
124.3352

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate

> <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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   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       1.334  -0.770   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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    7   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1                                                       
CONECT    8    4    9   30                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10                                                            
CONECT   13    9   14   18                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16                                                            
CONECT   25   15                                                            
CONECT   26   14   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    8                                                            
CONECT   31    1   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H](O)[C@@H]1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C25H24O12/c1-10(26)34-9-18-21(31)23(33)25(35-11(2)27)24(37-18)20-15(30)8-17-19(22(20)32)14(29)7-16(36-17)12-3-5-13(28)6-4-12/h3-8,18,21,23-25,28,30-33H,9H2,1-2H3/t18-,21-,23+,24+,25-/m1/s1

InChI Key

KMFYISKCEINRIB-WIOLZNRFSA-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
Crotalaria thebaica	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
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.38	ALOGPS
logP	0.83	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.34 m³·mol⁻¹	ChemAxon
Polarizability	51.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00014079

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

163104742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2'',6''-Di-O-Acetyl isovitexin (NP0060353)

MOL for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

3D MOL for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

3D SDF for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

3D-SDF for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

PDB for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

3D PDB for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

SMILES for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

INCHI for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

Structure for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)

3D Structure for NP0060353 (2'',6''-Di-O-Acetyl isovitexin)