NP-MRD: Showing NP-Card for 7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one (NP0214338)

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Record Information

Version

2.0

Created at

2022-09-05 13:36:37 UTC

Updated at

2022-09-05 13:36:38 UTC

NP-MRD ID

NP0214338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one

Description

Licoagroside A belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Licoagroside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Licoagroside A has been detected, but not quantified in, herbs and spices and tea. 7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one is found in Glycyrrhiza glabra. This could make licoagroside a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308282D          

 35 38  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308282D          

 35 38  0  0  0  0            999 V2000
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    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0214338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C(OC2OC(CO)C(O)C(O)C2O)=C1)C1=COC2=CC(O)=C(OC)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O12/c1-31-16-4-10-14(5-13(16)26)33-8-11(19(10)27)9-3-12(25)17(32-2)6-15(9)34-23-22(30)21(29)20(28)18(7-24)35-23/h3-6,8,18,20-26,28-30H,7H2,1-2H3

> <INCHI_KEY>
RQLOWOYMKFVTBB-UHFFFAOYSA-N

> <FORMULA>
C23H24O12

> <MOLECULAR_WEIGHT>
492.4295

> <EXACT_MASS>
492.126776232

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
47.019243117543

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
-0.1565382350000003

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.576305762362024

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.916857582938636

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462283103

> <JCHEM_POLAR_SURFACE_AREA>
184.59999999999994

> <JCHEM_REFRACTIVITY>
116.75369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      14.671  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.671   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
CONECT    1   31                                                            
CONECT    2   32                                                            
CONECT    3    9   12                                                       
CONECT    4   10   16                                                       
CONECT    5   13   14                                                       
CONECT    6   15   17                                                       
CONECT    7   18   24                                                       
CONECT    8   11   33                                                       
CONECT    9    3   11   15                                                  
CONECT   10    4   14   19                                                  
CONECT   11    8    9   19                                                  
CONECT   12    3   17   25                                                  
CONECT   13    5   16   26                                                  
CONECT   14    5   10   33                                                  
CONECT   15    6    9   34                                                  
CONECT   16    4   13   31                                                  
CONECT   17    6   12   32                                                  
CONECT   18    7   20   35                                                  
CONECT   19   10   11   27                                                  
CONECT   20   18   21   28                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   34   35                                                  
CONECT   24    7                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31    1   16                                                       
CONECT   32    2   17                                                       
CONECT   33    8   14                                                       
CONECT   34   15   23                                                       
CONECT   35   18   23                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
7,2',5'-Trihydroxy-6,4'-dimethoxyisoflavone 2'-O-glucoside	HMDB

Chemical Formula

C₂₃H₂₄O₁₂

Average Mass

492.4295 Da

Monoisotopic Mass

492.12678 Da

IUPAC Name

7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxy-4H-chromen-4-one

Traditional Name

7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C(OC2OC(CO)C(O)C(O)C2O)=C1)C1=COC2=CC(O)=C(OC)C=C2C1=O

InChI Identifier

InChI=1S/C23H24O12/c1-31-16-4-10-14(5-13(16)26)33-8-11(19(10)27)9-3-12(25)17(32-2)6-15(9)34-23-22(30)21(29)20(28)18(7-24)35-23/h3-6,8,18,20-26,28-30H,7H2,1-2H3

InChI Key

RQLOWOYMKFVTBB-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 glabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3'-hydroxy,4'-methoxyisoflavonoid
4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
Chromone
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
4-alkoxyphenol
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Pyran
Oxane
Benzenoid
Heteroaromatic compound
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
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	0.61	ALOGPS
logP	-0.16	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.75 m³·mol⁻¹	ChemAxon
Polarizability	47.02 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

HMDB0035448

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014132

KNApSAcK ID

C00019028

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

131751758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one (NP0214338)

MOL for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

3D MOL for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

3D SDF for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

3D-SDF for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

PDB for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

3D PDB for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

SMILES for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

INCHI for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

Structure for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)

3D Structure for NP0214338 (7-hydroxy-3-(5-hydroxy-4-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6-methoxychromen-4-one)