NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0182915)

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Record Information

Version

2.0

Created at

2022-09-03 21:43:54 UTC

Updated at

2022-09-03 21:43:54 UTC

NP-MRD ID

NP0182915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Description

[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. [(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate is found in Haplophyllum acutifolium. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032223432D          

 39 42  0  0  1  0            999 V2000
   -1.4289    2.4750    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

  Mrv1652309032223432D          

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 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  6 34  2  0  0  0  0
 34 35  1  0  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O14/c1-9(26)36-8-15-17(29)19(31)21(33)25(38-15)37-14-7-12(28)16-18(30)20(32)22(39-24(16)23(14)35-3)10-4-5-11(27)13(6-10)34-2/h4-7,15,17,19,21,25,27-29,31-33H,8H2,1-3H3/t15-,17-,19+,21-,25-/m1/s1

> <INCHI_KEY>
HKJIEFCRBAQGKS-UXVSBURRSA-N

> <FORMULA>
C25H26O14

> <MOLECULAR_WEIGHT>
550.469

> <EXACT_MASS>
550.132255517

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.01140568715653

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_LOGP>
0.31757957133333287

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.767273643820369

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.557094987332992

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028352059525

> <JCHEM_POLAR_SURFACE_AREA>
210.89999999999998

> <JCHEM_REFRACTIVITY>
129.10360000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   14   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    8   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    6   35                                                  
CONECT   35   34                                                            
CONECT   36    5   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₂₆O₁₄

Average Mass

550.4690 Da

Monoisotopic Mass

550.13226 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C2O1

InChI Identifier

InChI=1S/C25H26O14/c1-9(26)36-8-15-17(29)19(31)21(33)25(38-15)37-14-7-12(28)16-18(30)20(32)22(39-24(16)23(14)35-3)10-4-5-11(27)13(6-10)34-2/h4-7,15,17,19,21,25,27-29,31-33H,8H2,1-3H3/t15-,17-,19+,21-,25-/m1/s1

InChI Key

HKJIEFCRBAQGKS-UXVSBURRSA-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
Haplophyllum acutifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Polyol
Ether
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	0.32	ChemAxon
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	210.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.1 m³·mol⁻¹	ChemAxon
Polarizability	53.01 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

163188978

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)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate (NP0182915)

MOL for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

PDB for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

SMILES for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

INCHI for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

Structure for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0182915 ([(2r,3s,4s,5r,6s)-6-{[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate)