NP-MRD: Showing NP-Card for (-)-Kurilensin B (NP0073600)

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Record Information

Version

2.0

Created at

2022-04-28 18:49:32 UTC

Updated at

2022-04-28 18:49:32 UTC

NP-MRD ID

NP0073600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Kurilensin B

Description

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]-4H-chromen-4-one 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. (-)-Kurilensin B is found in Sasa cernua and Sasa kurilensis var.gigantea. Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220492D          

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M  END

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  Mrv1652304282220492D          

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  3 20  1  0  0  0  0
 21  2  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  1  0  0  0
 31 34  1  6  0  0  0
 30 35  1  1  0  0  0
 24 36  1  1  0  0  0
 23 37  1  6  0  0  0
 37 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H]([C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O14/c26-6-16-20(33)24(39-25-22(35)19(32)13(31)7-36-25)23(38-16)18-12(30)5-15-17(21(18)34)11(29)4-14(37-15)8-1-2-9(27)10(28)3-8/h1-5,13,16,19-20,22-28,30-35H,6-7H2/t13-,16-,19+,20-,22-,23-,24+,25+/m1/s1

> <INCHI_KEY>
LSHJORFPRQVMOA-TUMKRPRASA-N

> <FORMULA>
C25H26O14

> <MOLECULAR_WEIGHT>
550.469

> <EXACT_MASS>
550.132255517

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.06605149425434

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
-0.8643628546666661

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.710272451157822

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.137494203675037

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806646276365

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999997

> <JCHEM_REFRACTIVITY>
128.50139999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]chromen-4-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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.828  -4.612   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.335  -4.932   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.105  -3.598   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.074  -2.454   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.394  -0.947   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.859  -0.471   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -7.003  -1.502   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.468  -1.026   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.788   0.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.644   1.511   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.179   1.035   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.035   2.065   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -7.964   3.017   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -10.253   0.956   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -6.636  -3.437   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.961  -6.339   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.493  -6.500   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    3                                                            
CONECT   21    2   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   36                                                  
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   31                                                            
CONECT   35   30                                                            
CONECT   36   24                                                            
CONECT   37   23   38                                                       
CONECT   38   37                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₁₄

Average Mass

550.4690 Da

Monoisotopic Mass

550.13226 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxolan-2-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H]([C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C25H26O14/c26-6-16-20(33)24(39-25-22(35)19(32)13(31)7-36-25)23(38-16)18-12(30)5-15-17(21(18)34)11(29)4-14(37-15)8-1-2-9(27)10(28)3-8/h1-5,13,16,19-20,22-28,30-35H,6-7H2/t13-,16-,19+,20-,22-,23-,24+,25+/m1/s1

InChI Key

LSHJORFPRQVMOA-TUMKRPRASA-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
Sasa cernua	LOTUS Database	35616633
Sasa kurilensis var.gigantea	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
3'-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	0.13	ALOGPS
logP	-0.86	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3.5	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	128.5 m³·mol⁻¹	ChemAxon
Polarizability	53.07 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

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

163090459

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Kurilensin B (NP0073600)

MOL for NP0073600 ((-)-Kurilensin B)

3D MOL for NP0073600 ((-)-Kurilensin B)

3D SDF for NP0073600 ((-)-Kurilensin B)

3D-SDF for NP0073600 ((-)-Kurilensin B)

PDB for NP0073600 ((-)-Kurilensin B)

3D PDB for NP0073600 ((-)-Kurilensin B)

SMILES for NP0073600 ((-)-Kurilensin B)

INCHI for NP0073600 ((-)-Kurilensin B)

Structure for NP0073600 ((-)-Kurilensin B)

3D Structure for NP0073600 ((-)-Kurilensin B)