NP-MRD: Showing NP-Card for 2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one (NP0262191)

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Record Information

Version

2.0

Created at

2022-09-08 04:51:53 UTC

Updated at

2022-09-08 04:51:53 UTC

NP-MRD ID

NP0262191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

Description

Liquiritin apioside 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. Liquiritin apioside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Liquiritin apioside has been detected, but not quantified in, herbs and spices and tea. 2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one is found in Glycyrrhiza uralensis. This could make liquiritin apioside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241208502D          

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M  END

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  Mrv0541 02241208502D          

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  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 29  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 35  1  0  0  0  0
 27 28  1  0  0  0  0
 27 33  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
 30 39  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 38  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3)C(OC2OCC(O)(CO)C2O)C(O)C1O

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

> <INCHI_KEY>
FTVKHUHJWDMWIR-UHFFFAOYSA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.5086

> <EXACT_MASS>
550.168641046

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
55.186628693532285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-1.0558937813333324

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.807383168292008

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.79793301897353

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092569267272

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
128.12349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -9.619   2.004   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.285   2.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.952   2.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.618   2.774   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.283   2.004   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.951   2.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.951   4.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.283   5.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.618   4.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.952   5.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.285   4.314   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.283   6.624   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.617   2.004   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.617   0.464   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.285  -0.305   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.050   0.464   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.050   2.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.285   2.774   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.384  -0.305   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.716   0.464   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.716   2.004   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.051   2.774   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.051   4.314   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.383   5.084   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.400  -5.176   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.545  -4.147   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.383  -2.615   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.051  -1.845   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.051  -0.305   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.383   0.464   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.383   2.004   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.717   2.774   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.792  -1.989   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.821  -3.134   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.051  -4.468   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.458  -5.095   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.619  -6.624   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       7.576  -5.931   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.717  -0.305   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    2   10                                                       
CONECT   12    8                                                            
CONECT   13    6   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26   25   27   35                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   20   28   30                                                  
CONECT   30   29   31   39                                                  
CONECT   31   22   30   32                                                  
CONECT   32   31                                                            
CONECT   33   27   34                                                       
CONECT   34   33   35                                                       
CONECT   35   26   34   36   38                                             
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   30                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5086 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3)C(OC2OCC(O)(CO)C2O)C(O)C1O

InChI Identifier

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

InChI Key

FTVKHUHJWDMWIR-UHFFFAOYSA-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
Glycyrrhiza uralensis	LOTUS Database	35616633

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-4p-o-glycoside
Flavonoid o-glycoside
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
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	-0.12	ALOGPS
logP	-1.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.12 m³·mol⁻¹	ChemAxon
Polarizability	55.19 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

HMDB0037491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016564

KNApSAcK ID

C00008195

Chemspider ID

22370325

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45360052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one (NP0262191)

MOL for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0262191 (2-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)