NP-MRD: Showing NP-Card for Butein 4'-arabinosyl-(1->4)-galactoside (NP0054891)

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Record Information

Version

2.0

Created at

2022-04-28 01:05:53 UTC

Updated at

2022-04-28 01:05:53 UTC

NP-MRD ID

NP0054891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butein 4'-arabinosyl-(1->4)-galactoside

Description

(2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)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. Butein 4'-arabinosyl-(1->4)-galactoside is found in Bauhinia purpurea . Based on a literature review very few articles have been published on (2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203052D          

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 22 40  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282203052D          

 40 43  0  0  1  0            999 V2000
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    5.0013    1.2375    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
 13 18  1  0  0  0  0
  3 19  1  0  0  0  0
  1 20  1  0  0  0  0
 21 20  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
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 24 29  1  1  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  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
 30 35  1  0  0  0  0
 33 36  1  6  0  0  0
 32 37  1  1  0  0  0
 31 38  1  1  0  0  0
 23 39  1  1  0  0  0
 22 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0054891

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O14/c27-9-19-24(40-25-22(35)20(33)18(32)10-37-25)21(34)23(36)26(39-19)38-12-3-4-13(16(30)8-12)14(28)5-1-11-2-6-15(29)17(31)7-11/h1-8,18-27,29-36H,9-10H2/b5-1+/t18-,19+,20+,21-,22+,23-,24+,25+,26-/m1/s1

> <INCHI_KEY>
UEBCNBNOYVLOPQ-CJKGMVBPSA-N

> <FORMULA>
C26H30O14

> <MOLECULAR_WEIGHT>
566.512

> <EXACT_MASS>
566.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.17953506692716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.082504774666666

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.005336855338193

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.047708312552116

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806620518916

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999997

> <JCHEM_REFRACTIVITY>
133.3958

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -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       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -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       2.667 -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      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      20.005  -0.770   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      20.005   2.310   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      17.338   3.850   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
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    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39   23                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₄

Average Mass

566.5120 Da

Monoisotopic Mass

566.16356 Da

IUPAC Name

(2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-(4-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H30O14/c27-9-19-24(40-25-22(35)20(33)18(32)10-37-25)21(34)23(36)26(39-19)38-12-3-4-13(16(30)8-12)14(28)5-1-11-2-6-15(29)17(31)7-11/h1-8,18-27,29-36H,9-10H2/b5-1+/t18-,19+,20+,21-,22+,23-,24+,25+,26-/m1/s1

InChI Key

UEBCNBNOYVLOPQ-CJKGMVBPSA-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
Bauhinia purpurea	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
Phenoxy compound
Aryl ketone
Styrene
Phenol ether
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	-0.27	ALOGPS
logP	-0.083	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.05	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.4 m³·mol⁻¹	ChemAxon
Polarizability	55.18 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

162987793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Butein 4'-arabinosyl-(1->4)-galactoside (NP0054891)

MOL for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

3D MOL for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

3D SDF for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

3D-SDF for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

PDB for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

3D PDB for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

SMILES for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

INCHI for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

Structure for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)

3D Structure for NP0054891 (Butein 4'-arabinosyl-(1->4)-galactoside)