NP-MRD: Showing NP-Card for (2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate (NP0165327)

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Record Information

Version

2.0

Created at

2022-09-03 00:25:55 UTC

Updated at

2022-09-03 00:25:55 UTC

NP-MRD ID

NP0165327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate

Description

(2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Based on a literature review very few articles have been published on (2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202252D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032202252D          

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  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0165327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O11/c1-3-11(2)26(34)37-25-22(33)21(32)18(10-27)36-24(25)20-15(30)8-14(29)19-16(31)9-17(35-23(19)20)12-4-6-13(28)7-5-12/h4-9,11,18,21-22,24-25,27-30,32-33H,3,10H2,1-2H3/t11-,18+,21-,22+,24+,25+/m1/s1

> <INCHI_KEY>
WEAUPFXXCUHVAE-FFGPMPPSSA-N

> <FORMULA>
C26H28O11

> <MOLECULAR_WEIGHT>
516.499

> <EXACT_MASS>
516.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.680883538332495

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.0785844293333318

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.001037186098076

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.17248344678006

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791932576422955

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
128.98610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate

> <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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -4.620   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  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   30                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   20   29                                                       
CONECT   29   28   10   16                                                  
CONECT   30    9   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    8   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4S,5S,6S)-2-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₆H₂₈O₁₁

Average Mass

516.4990 Da

Monoisotopic Mass

516.16316 Da

IUPAC Name

(2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate

Traditional Name

(2S,3S,4S,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C26H28O11/c1-3-11(2)26(34)37-25-22(33)21(32)18(10-27)36-24(25)20-15(30)8-14(29)19-16(31)9-17(35-23(19)20)12-4-6-13(28)7-5-12/h4-9,11,18,21-22,24-25,27-30,32-33H,3,10H2,1-2H3/t11-,18+,21-,22+,24+,25+/m1/s1

InChI Key

WEAUPFXXCUHVAE-FFGPMPPSSA-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 flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Primary alcohol
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	2.24	ALOGPS
logP	2.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.99 m³·mol⁻¹	ChemAxon
Polarizability	50.68 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

163188580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate (NP0165327)

MOL for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

3D MOL for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

3D SDF for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

3D-SDF for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

PDB for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

3D PDB for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

SMILES for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

INCHI for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

Structure for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)

3D Structure for NP0165327 ((2s,3s,4s,5s,6s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2r)-2-methylbutanoate)