NP-MRD: Showing NP-Card for Okanin 4'-(3'',4'',6''-triacetylglucoside) (NP0055263)

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Record Information

Version

2.0

Created at

2022-04-28 01:22:52 UTC

Updated at

2022-04-28 01:22:52 UTC

NP-MRD ID

NP0055263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Okanin 4'-(3'',4'',6''-triacetylglucoside)

Description

Okanin 4'-(3'',4'',6''-triacetylglucoside) belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, okanin 4'-(3'',4'',6''-triacetylglucoside) is considered to be a flavonoid. Okanin 4'-(3'',4'',6''-triacetylglucoside) is found in Bidens pilosa and Senecio pseudotites. Based on a literature review very few articles have been published on Okanin 4'-(3'',4'',6''-triacetylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203222D          

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M  END

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 13 18  1  0  0  0  0
  3 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 25 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 24 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 23 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0055263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=C(O)C(O)=C(C=C2)C(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O14/c1-12(28)37-11-21-25(38-13(2)29)26(39-14(3)30)24(36)27(41-21)40-20-9-6-16(22(34)23(20)35)17(31)7-4-15-5-8-18(32)19(33)10-15/h4-10,21,24-27,32-36H,11H2,1-3H3/b7-4+/t21-,24-,25-,26-,27-/m1/s1

> <INCHI_KEY>
CKEPCIVNAQZGCM-IBLDPMEOSA-N

> <FORMULA>
C27H28O14

> <MOLECULAR_WEIGHT>
576.507

> <EXACT_MASS>
576.147905582

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.03757269542638

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{4-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy}-5-hydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.0778068383333332

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.009592078807383

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.318004371128359

> <JCHEM_PKA_STRONGEST_BASIC>
-3.969632503754455

> <JCHEM_POLAR_SURFACE_AREA>
215.57999999999998

> <JCHEM_REFRACTIVITY>
136.38039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{4-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy}-5-hydroxyoxan-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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18   13                                                            
CONECT   19    3                                                            
CONECT   20    2                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   41                                                  
CONECT   24   23   25   37                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   25   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   24   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₁₄

Average Mass

576.5070 Da

Monoisotopic Mass

576.14791 Da

IUPAC Name

[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{4-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy}-5-hydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{4-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy}-5-hydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=C(O)C(O)=C(C=C2)C(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H28O14/c1-12(28)37-11-21-25(38-13(2)29)26(39-14(3)30)24(36)27(41-21)40-20-9-6-16(22(34)23(20)35)17(31)7-4-15-5-8-18(32)19(33)10-15/h4-10,21,24-27,32-36H,11H2,1-3H3/b7-4+/t21-,24-,25-,26-,27-/m1/s1

InChI Key

CKEPCIVNAQZGCM-IBLDPMEOSA-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
Bidens pilosa	LOTUS Database	35616633
Senecio pseudotites	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-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 O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Phenolic glycoside
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Benzoyl
Aryl ketone
Styrene
Phenoxy compound
Phenol ether
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Oxane
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.86	ALOGPS
logP	2.08	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	215.58 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	136.38 m³·mol⁻¹	ChemAxon
Polarizability	56.04 Å³	ChemAxon
Number of Rings	3	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

C00007898

Chemspider ID

23339380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14861259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Okanin 4'-(3'',4'',6''-triacetylglucoside) (NP0055263)

MOL for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

3D MOL for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

3D SDF for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

3D-SDF for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

PDB for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

3D PDB for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

SMILES for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

INCHI for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

Structure for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))

3D Structure for NP0055263 (Okanin 4'-(3'',4'',6''-triacetylglucoside))