NP-MRD: Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0311428)

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Record Information

Version

2.0

Created at

2022-09-11 07:24:43 UTC

Updated at

2022-09-11 07:24:43 UTC

NP-MRD ID

NP0311428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

Description

Afrormosin 7-o-(6''-malonylglucoside) belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, afrormosin 7-O-(6''-malonylglucoside) is considered to be a flavonoid. 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid is found in Glycyrrhiza glabra. Based on a literature review very few articles have been published on Afrormosin 7-o-(6''-malonylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209242D          

 39 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112209242D          

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 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  6  0  0  0
 12 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
 10 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  2  0  0  0  0
  6 38  1  0  0  0  0
 38 39  2  0  0  0  0
  3 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]3O)=C(OC)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O13/c1-34-13-5-3-12(4-6-13)15-10-36-16-8-18(17(35-2)7-14(16)22(15)30)38-26-25(33)24(32)23(31)19(39-26)11-37-21(29)9-20(27)28/h3-8,10,19,23-26,31-33H,9,11H2,1-2H3,(H,27,28)/t19-,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
HOWDEROVXAADRI-OMJUENHASA-N

> <FORMULA>
C26H26O13

> <MOLECULAR_WEIGHT>
546.481

> <EXACT_MASS>
546.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.43729609890389

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_LOGP>
0.7839462646666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.201579990190467

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.350229586579688

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103045628454

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
128.2875

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   38                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   30                                                  
CONECT   30   29                                                            
CONECT   31   12   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35                                                       
CONECT   35   34   10   36                                                  
CONECT   36   35    7   37                                                  
CONECT   37   36                                                            
CONECT   38    6   39                                                       
CONECT   39   38    3                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₆O₁₃

Average Mass

546.4810 Da

Monoisotopic Mass

546.13734 Da

IUPAC Name

3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

Traditional Name

3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]3O)=C(OC)C=C2C1=O

InChI Identifier

InChI=1S/C26H26O13/c1-34-13-5-3-12(4-6-13)15-10-36-16-8-18(17(35-2)7-14(16)22(15)30)38-26-25(33)24(32)23(31)19(39-26)11-37-21(29)9-20(27)28/h3-8,10,19,23-26,31-33H,9,11H2,1-2H3,(H,27,28)/t19-,23-,24+,25-,26-/m1/s1

InChI Key

HOWDEROVXAADRI-OMJUENHASA-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 isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
4p-o-methylisoflavone
Isoflavone
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	0.78	ChemAxon
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.29 m³·mol⁻¹	ChemAxon
Polarizability	53.44 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

C00010169

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

101089085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0311428)

MOL for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D MOL for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D SDF for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D-SDF for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

PDB for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D PDB for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

SMILES for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

INCHI for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

Structure for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D Structure for NP0311428 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[6-methoxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid)