NP-MRD: Showing NP-Card for 1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate (NP0188030)

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Record Information

Version

2.0

Created at

2022-09-04 04:17:32 UTC

Updated at

2022-09-04 04:17:32 UTC

NP-MRD ID

NP0188030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate

Description

1-Ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl propanedioate 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. 1-Ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl propanedioate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261503512D          

 39 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004261503512D          

 39 42  0  0  0  0            999 V2000
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 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 15 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC(=O)OCC1OC(OC2=CC=C3C(OC=C(C3=O)C3=CC=C(OC)C=C3)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c1-3-35-21(28)11-22(29)37-13-20-24(31)25(32)26(33)27(39-20)38-16-8-9-17-19(10-16)36-12-18(23(17)30)14-4-6-15(34-2)7-5-14/h4-10,12,20,24-27,31-33H,3,11,13H2,1-2H3

> <INCHI_KEY>
WBHHUJMFEZNDBL-UHFFFAOYSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.433941677615735

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl propanedioate

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.4443195409999996

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.702267469188058

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.081640893042122

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103025378725

> <JCHEM_POLAR_SURFACE_AREA>
167.28000000000003

> <JCHEM_REFRACTIVITY>
131.34200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      21.339  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.006  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.340  -3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      26.674  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.007  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.341  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      30.675  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      32.008  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      33.342  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.676  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.009  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.009  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.343  -6.160   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      38.677  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      37.343  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.009  -8.470   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      34.676  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      34.676  -6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.677  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      40.010  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.344  -8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      41.344 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      42.678 -10.780   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      44.011 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      40.010 -10.780   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      38.677 -10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      32.008  -6.160   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      29.341  -6.160   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      29.341  -7.700   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      28.007  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      26.674  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   15                                                       
CONECT   26   21   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   26                                                       
CONECT   34   13   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   11   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
1-Ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl propanedioic acid	Generator

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl propanedioate

Traditional Name

1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate

CAS Registry Number

Not Available

SMILES

CCOC(=O)CC(=O)OCC1OC(OC2=CC=C3C(OC=C(C3=O)C3=CC=C(OC)C=C3)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H28O12/c1-3-35-21(28)11-22(29)37-13-20-24(31)25(32)26(33)27(39-20)38-16-8-9-17-19(10-16)36-12-18(23(17)30)14-4-6-15(34-2)7-5-14/h4-10,12,20,24-27,31-33H,3,11,13H2,1-2H3

InChI Key

WBHHUJMFEZNDBL-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

Not Available

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
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Ether
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
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	1.85	ALOGPS
logP	1.44	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	167.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	131.34 m³·mol⁻¹	ChemAxon
Polarizability	54.43 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate (NP0188030)

MOL for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

3D MOL for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

3D SDF for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

3D-SDF for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

PDB for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

3D PDB for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

SMILES for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

INCHI for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

Structure for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)

3D Structure for NP0188030 (1-ethyl 3-(3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl propanedioate)