NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate (NP0305057)

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Record Information

Version

2.0

Created at

2022-09-10 20:34:11 UTC

Updated at

2022-09-10 20:34:11 UTC

NP-MRD ID

NP0305057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate

Description

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate 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. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate is found in Ammopiptanthus mongolicus. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222342D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102222342D          

 36 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0305057

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O10/c1-3-4-21(27)34-13-20-23(29)24(30)25(31)26(36-20)35-16-9-10-17-19(11-16)33-12-18(22(17)28)14-5-7-15(32-2)8-6-14/h3-12,20,23-26,29-31H,13H2,1-2H3/b4-3+/t20-,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
UNGLMQNWMJMOML-SFXFPITBSA-N

> <FORMULA>
C26H26O10

> <MOLECULAR_WEIGHT>
498.484

> <EXACT_MASS>
498.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.58155994352768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate

> <JCHEM_LOGP>
2.425650419333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.21068742881344

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20170488382106

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110288859882

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
125.80140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000  -9.240   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                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   19                                                       
CONECT   27   18   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29   12                                                       
CONECT   31   10   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    8   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoic acid	Generator

Chemical Formula

C₂₆H₂₆O₁₀

Average Mass

498.4840 Da

Monoisotopic Mass

498.15260 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-but-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H26O10/c1-3-4-21(27)34-13-20-23(29)24(30)25(31)26(36-20)35-16-9-10-17-19(11-16)33-12-18(22(17)28)14-5-7-15(32-2)8-6-14/h3-12,20,23-26,29-31H,13H2,1-2H3/b4-3+/t20-,23-,24+,25-,26-/m1/s1

InChI Key

UNGLMQNWMJMOML-SFXFPITBSA-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
Ammopiptanthus mongolicus	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
Saccharolipid
Isoflavone
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Fatty acid ester
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Pyran
Oxane
Benzenoid
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Polyol
Ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.43	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.8 m³·mol⁻¹	ChemAxon
Polarizability	50.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163189312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate (NP0305057)

MOL for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

3D MOL for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

3D SDF for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

3D-SDF for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

PDB for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

3D PDB for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

SMILES for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

INCHI for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

Structure for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)

3D Structure for NP0305057 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2e)-but-2-enoate)