NP-MRD: Showing NP-Card for Chalconaringenin 2'-(6''-p-coumarylglucoside) (NP0055246)

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Record Information

Version

2.0

Created at

2022-04-28 01:22:07 UTC

Updated at

2022-04-28 01:22:07 UTC

NP-MRD ID

NP0055246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chalconaringenin 2'-(6''-p-coumarylglucoside)

Description

[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate 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. Chalconaringenin 2'-(6''-p-coumarylglucoside) is found in Salix interior. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203222D          

 42 45  0  0  1  0            999 V2000
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 21 41  1  6  0  0  0
  1 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282203222D          

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    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  3 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
 23 39  1  1  0  0  0
 22 40  1  1  0  0  0
 21 41  1  6  0  0  0
  1 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C(C(=O)\C=C\C3=CC=C(O)C=C3)C(O)=CC(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O12/c31-18-7-1-16(2-8-18)5-11-21(34)26-22(35)13-20(33)14-23(26)41-30-29(39)28(38)27(37)24(42-30)15-40-25(36)12-6-17-3-9-19(32)10-4-17/h1-14,24,27-33,35,37-39H,15H2/b11-5+,12-6+/t24-,27+,28+,29-,30-/m1/s1

> <INCHI_KEY>
WGZRJKFSELNVFI-NKTIHWTASA-N

> <FORMULA>
C30H28O12

> <MOLECULAR_WEIGHT>
580.542

> <EXACT_MASS>
580.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.59360695524043

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.7883213253333325

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.520611504586297

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.142454031496225

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491102942232816

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
148.49360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001 -10.010   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      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -12.003 -19.250   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2    6   42                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   41                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   35                                                            
CONECT   39   23                                                            
CONECT   40   22                                                            
CONECT   41   21                                                            
CONECT   42    1                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₀H₂₈O₁₂

Average Mass

580.5420 Da

Monoisotopic Mass

580.15808 Da

IUPAC Name

[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3R,4S,5R,6S)-6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C(C(=O)\C=C\C3=CC=C(O)C=C3)C(O)=CC(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H28O12/c31-18-7-1-16(2-8-18)5-11-21(34)26-22(35)13-20(33)14-23(26)41-30-29(39)28(38)27(37)24(42-30)15-40-25(36)12-6-17-3-9-19(32)10-4-17/h1-14,24,27-33,35,37-39H,15H2/b11-5+,12-6+/t24-,27+,28+,29-,30-/m1/s1

InChI Key

WGZRJKFSELNVFI-NKTIHWTASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Salix interior	Plant	KNApSAcK

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 o-glycoside
2'-hydroxychalcone
Phenolic glycoside
Cinnamylphenol
Linear 1,3-diarylpropanoid
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Phenoxy compound
Aryl ketone
Styrene
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Acryloyl-group
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.91	ALOGPS
logP	3.79	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	148.49 m³·mol⁻¹	ChemAxon
Polarizability	57.59 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

162943297

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Chalconaringenin 2'-(6''-p-coumarylglucoside) (NP0055246)

MOL for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

3D MOL for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

3D SDF for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

3D-SDF for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

PDB for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

3D PDB for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

SMILES for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

INCHI for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

Structure for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))

3D Structure for NP0055246 (Chalconaringenin 2'-(6''-p-coumarylglucoside))