NP-MRD: Showing NP-Card for Licuroside (NP0054871)

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Record Information

Version

2.0

Created at

2022-04-28 01:05:09 UTC

Updated at

2022-04-28 01:05:09 UTC

NP-MRD ID

NP0054871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Licuroside

Description

(2Z)-3-(4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(2,4-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. Licuroside is found in Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata, Glycyrrhiza sp. and Glycyrrhiza uralensis . Based on a literature review very few articles have been published on (2Z)-3-(4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203052D          

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M  END

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  Mrv1652304282203052D          

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  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
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 27 30  1  1  0  0  0
 27 31  1  6  0  0  0
 31 32  1  0  0  0  0
 26 33  1  1  0  0  0
 22 34  1  6  0  0  0
 21 35  1  6  0  0  0
 20 36  1  6  0  0  0
 36 37  1  0  0  0  0
  3 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(\C=C/C(=O)C3=C(O)C=C(O)C=C3)C=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3-/t19-,20+,21+,22-,23+,24-,25+,26-/m1/s1

> <INCHI_KEY>
VMMVZVPAYFZNBM-SEXNULBASA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.513

> <EXACT_MASS>
550.168641026

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.44525879769984

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
0.08506219066666768

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.74936624644073

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.116170883704453

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925692672834

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999998

> <JCHEM_REFRACTIVITY>
131.6343

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(2,4-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      19.492   0.883   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.587   2.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.055   1.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.429   0.561   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.334  -0.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.865  -0.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.897   0.400   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.271  -1.007   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.992   1.646   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.460   1.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.834   0.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.739  -1.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.113  -2.575   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.581  -2.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.676  -1.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.302  -0.083   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.955  -4.142   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.423  -4.303   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.797  -5.710   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.265  -5.871   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.360  -4.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.986  -3.219   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.518  -3.058   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.144  -1.651   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.715   1.060   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.469   1.965   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.223   1.060   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.699  -0.405   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.225   3.307   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.713   3.307   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.497   4.632   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.180   1.536   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.081  -1.973   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.829  -4.786   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.639  -7.278   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.107  -7.439   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      16.150   3.214   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      21.023   1.044   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
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                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   36                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   30   31                                             
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   27                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   26                                                            
CONECT   34   22                                                            
CONECT   35   21                                                            
CONECT   36   20   37                                                       
CONECT   37   36                                                            
CONECT   38    3                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5130 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(\C=C/C(=O)C3=C(O)C=C(O)C=C3)C=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3-/t19-,20+,21+,22-,23+,24-,25+,26-/m1/s1

InChI Key

VMMVZVPAYFZNBM-SEXNULBASA-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
Glycyrrhiza aspera	LOTUS Database	35616633
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	LOTUS Database	35616633
Glycyrrhiza sp.	Plant	KNApSAcK
Glycyrrhiza uralensis	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
O-glycosyl compound
Glycosyl compound
Disaccharide
Phenoxy compound
Aryl ketone
Styrene
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Tertiary alcohol
Enone
Acryloyl-group
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
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	-0.04	ALOGPS
logP	0.085	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.63 m³·mol⁻¹	ChemAxon
Polarizability	54.45 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

162881454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Licuroside (NP0054871)

MOL for NP0054871 (Licuroside)

3D MOL for NP0054871 (Licuroside)

3D SDF for NP0054871 (Licuroside)

3D-SDF for NP0054871 (Licuroside)

PDB for NP0054871 (Licuroside)

3D PDB for NP0054871 (Licuroside)

SMILES for NP0054871 (Licuroside)

INCHI for NP0054871 (Licuroside)

Structure for NP0054871 (Licuroside)

3D Structure for NP0054871 (Licuroside)