NP-MRD: Showing NP-Card for Leucoside (NP0140279)

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Record Information

Version

2.0

Created at

2022-06-29 21:21:09 UTC

Updated at

2022-06-29 21:21:09 UTC

NP-MRD ID

NP0140279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leucoside

Description

Leucoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Leucoside is found in Actinidia arguta, Aesculus chinensis, Aesculus hippocastanum, Melaleuca ericifolia, Phaseolus vulgaris, Pteridium esculentum, Rhodiola rosea and Spiranthes australis. Leucoside was first documented in 2013 (PMID: 22777867). Leucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309272006272D          

 41 45  0  0  0  0            999 V2000
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  5  6  1  0  0  0  0
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 36 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652309272006272D          

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 10 11  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 27  2  0  0  0  0
 26 25  2  0  0  0  0
 25 22  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  8  1  0  0  0  0
  2 14  1  1  0  0  0
  5  7  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 26  1  0  0  0  0
 14 15  1  0  0  0  0
  1  2  1  0  0  0  0
  3 16  1  6  0  0  0
  8  7  1  1  0  0  0
  4 17  1  1  0  0  0
  2  3  1  0  0  0  0
  6 18  1  1  0  0  0
 29 18  1  0  0  0  0
  3  4  1  0  0  0  0
 28 33  2  0  0  0  0
 13 19  1  6  0  0  0
 24 34  1  0  0  0  0
  4  5  1  0  0  0  0
 22 35  1  0  0  0  0
 12 20  1  1  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 36  1  0  0  0  0
 30 39  1  0  0  0  0
 36 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140279

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O15/c27-7-15-18(33)20(35)24(41-25-21(36)17(32)13(31)8-37-25)26(39-15)40-23-19(34)16-12(30)5-11(29)6-14(16)38-22(23)9-1-3-10(28)4-2-9/h1-6,13,15,17-18,20-21,24-33,35-36H,7-8H2/t13-,15-,17+,18-,20+,21-,24-,25+,26+/m1/s1

> <INCHI_KEY>
RXAXTTGJEMODPY-CJNLAGEVSA-N

> <FORMULA>
C26H28O15

> <MOLECULAR_WEIGHT>
580.495

> <EXACT_MASS>
580.142820202

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.36810021130175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.9817706779999993

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.869699239112584

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372347193147522

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580682626249

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
133.74539999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       9.771  -3.671   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.771  -5.211   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.108  -5.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.437  -5.211   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.437  -3.671   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.108  -2.901   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.772  -2.902   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.105  -3.673   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.098  -5.211   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.431  -5.982   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.766  -5.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.767  -3.673   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.434  -2.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.438  -5.982   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.438  -7.522   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.110  -7.521   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      13.695  -6.288   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.110  -1.361   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.432  -1.361   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.101  -2.903   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.099  -5.984   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.452   0.966   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.452  -0.573   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.789  -1.344   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.789   1.737   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.118   0.966   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.112  -0.573   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.442  -1.349   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.780  -0.585   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.786   0.955   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.455   1.731   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.130   4.009   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.436  -2.889   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.793  -2.884   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.119   1.737   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.787   3.249   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.457   4.017   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.126   3.249   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.126   1.713   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.457   0.944   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.787   1.713   0.000  0.00  0.00           C+0
CONECT    1    6    2                                                       
CONECT    2   14    1    3                                                  
CONECT    3   16    2    4                                                  
CONECT    4   17    3    5                                                  
CONECT    5    6    7    4                                                  
CONECT    6    5    1   18                                                  
CONECT    7    5    8                                                       
CONECT    8    9   13    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   21   10   12                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12    8   19                                                  
CONECT   14    2   15                                                       
CONECT   15   14                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    6   29                                                       
CONECT   19   13                                                            
CONECT   20   12                                                            
CONECT   21   11                                                            
CONECT   22   23   25   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   27   34                                                  
CONECT   25   26   22                                                       
CONECT   26   25   27   31                                                  
CONECT   27   24   26   28                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   18                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   26                                                       
CONECT   32   36                                                            
CONECT   33   28                                                            
CONECT   34   24                                                            
CONECT   35   22                                                            
CONECT   36   37   41   32                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   30                                                  
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Kaempferol 3-O-beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside	PhytoBank
Kaempferol 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside	PhytoBank
Kaempferol 3-O-beta-D-xylopyranosyl-(1→2)-beta-D-glucopyranoside	PhytoBank
Kaempferol-3-O-beta-xylopyranosyl-(1->2)-beta-glucopyranoside	PhytoBank
Kaempferol-3-O-β-xylopyranosyl-(1→2)-β-glucopyranoside	PhytoBank
Kaempferol-3-O-beta-xylopyranosyl-(1→2)-beta-glucopyranoside	PhytoBank
Kaempferol 3-O-sambubioside	PhytoBank
Kaempferol 3-sambubioside	PhytoBank

Chemical Formula

C₂₆H₂₈O₁₅

Average Mass

580.4950 Da

Monoisotopic Mass

580.14282 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H28O15/c27-7-15-18(33)20(35)24(41-25-21(36)17(32)13(31)8-37-25)26(39-15)40-23-19(34)16-12(30)5-11(29)6-14(16)38-22(23)9-1-3-10(28)4-2-9/h1-6,13,15,17-18,20-21,24-33,35-36H,7-8H2/t13-,15-,17+,18-,20+,21-,24-,25+,26+/m1/s1

InChI Key

RXAXTTGJEMODPY-CJNLAGEVSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Actinidia arguta	LOTUS Database	35616633
Aesculus chinensis	LOTUS Database	35616633
Aesculus hippocastanum	LOTUS Database	35616633
Melaleuca ericifolia	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Pteridium esculentum	LOTUS Database	35616633
Rhodiola rosea	LOTUS Database	35616633
Spiranthes australis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
Disaccharide
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Oxane
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	-0.3	ALOGPS
logP	-0.98	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.75 m³·mol⁻¹	ChemAxon
Polarizability	54.37 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	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

23339482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566720

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chung DW, Lee SB: Novel synthesis of leucoside by enzymatic hydrolysis of tea seed extract. J Sci Food Agric. 2013 Jan;93(2):362-7. doi: 10.1002/jsfa.5769. Epub 2012 Jul 6. [PubMed:22777867 ]

Showing NP-Card for Leucoside (NP0140279)

MOL for NP0140279 (Leucoside)

3D MOL for NP0140279 (Leucoside)

3D SDF for NP0140279 (Leucoside)

3D-SDF for NP0140279 (Leucoside)

PDB for NP0140279 (Leucoside)

3D PDB for NP0140279 (Leucoside)

SMILES for NP0140279 (Leucoside)

INCHI for NP0140279 (Leucoside)

Structure for NP0140279 (Leucoside)

3D Structure for NP0140279 (Leucoside)