NP-MRD: Showing NP-Card for Okanin 4-methyl ether 4'-primveroside (NP0055273)

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Record Information

Version

2.0

Created at

2022-04-28 01:23:14 UTC

Updated at

2022-04-28 01:23:14 UTC

NP-MRD ID

NP0055273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Okanin 4-methyl ether 4'-primveroside

Description

(2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 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. Okanin 4-methyl ether 4'-primveroside is found in Bidens campylotheca. Based on a literature review very few articles have been published on (2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203232D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282203232D          

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    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
  1 22  1  0  0  0  0
 23 22  1  6  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
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  6  0  0  0
 26 31  1  1  0  0  0
 25 32  1  1  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 34 35  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
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  1  0  0  0
 36 41  1  6  0  0  0
 35 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0055273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(\C=C\C(=O)C2=C(O)C(O)=C(O[C@@H]3O[C@@H](CO[C@H]4OC[C@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O15/c1-38-16-6-3-11(8-14(16)29)2-5-13(28)12-4-7-17(21(33)19(12)31)41-27-25(37)23(35)22(34)18(42-27)10-40-26-24(36)20(32)15(30)9-39-26/h2-8,15,18,20,22-27,29-37H,9-10H2,1H3/b5-2+/t15-,18-,20+,22+,23-,24-,25+,26+,27+/m0/s1

> <INCHI_KEY>
PGUVLBHFVSDWEY-PMEOJPSFSA-N

> <FORMULA>
C27H32O15

> <MOLECULAR_WEIGHT>
596.538

> <EXACT_MASS>
596.17412033

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.948508973928064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-0.24017604033333292

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.826957814011838

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.325753542490285

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486860135578283

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
139.85899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-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       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
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   19                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19   13                                                            
CONECT   20    3                                                            
CONECT   21    2                                                            
CONECT   22    1   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   26                                                            
CONECT   32   25   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36   42                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   37                                                            
CONECT   41   36                                                            
CONECT   42   35                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₅

Average Mass

596.5380 Da

Monoisotopic Mass

596.17412 Da

IUPAC Name

(2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-(2,3-dihydroxy-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(\C=C\C(=O)C2=C(O)C(O)=C(O[C@@H]3O[C@@H](CO[C@H]4OC[C@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1

InChI Identifier

InChI=1S/C27H32O15/c1-38-16-6-3-11(8-14(16)29)2-5-13(28)12-4-7-17(21(33)19(12)31)41-27-25(37)23(35)22(34)18(42-27)10-40-26-24(36)20(32)15(30)9-39-26/h2-8,15,18,20,22-27,29-37H,9-10H2,1H3/b5-2+/t15-,18-,20+,22+,23-,24-,25+,26+,27+/m0/s1

InChI Key

PGUVLBHFVSDWEY-PMEOJPSFSA-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 campylotheca	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
Phenolic glycoside
Cinnamylphenol
Linear 1,3-diarylpropanoid
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Methoxyphenol
Phenoxy compound
Methoxybenzene
Aryl ketone
Styrene
Phenol ether
Catechol
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	-0.15	ALOGPS
logP	-0.24	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.86 m³·mol⁻¹	ChemAxon
Polarizability	57.95 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	Yes	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

163033562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Okanin 4-methyl ether 4'-primveroside (NP0055273)

MOL for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

3D MOL for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

3D SDF for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

3D-SDF for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

PDB for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

3D PDB for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

SMILES for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

INCHI for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

Structure for NP0055273 (Okanin 4-methyl ether 4'-primveroside)

3D Structure for NP0055273 (Okanin 4-methyl ether 4'-primveroside)