NP-MRD: Showing NP-Card for 2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0331069)

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Record Information

Version

1.0

Created at

2022-09-12 17:03:09 UTC

Updated at

2022-09-12 17:03:09 UTC

NP-MRD ID

NP0331069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{2-[1-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. 2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Brainea insignis and Epimedium grandiflorum. 2-{2-[1-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310151720182D          

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M  END

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  Mrv1652310151720182D          

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 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 26  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
 37 32  1  0  0  0  0
 32  6  1  0  0  0  0
 33  4  1  0  0  0  0
  3 35  1  0  0  0  0
 28  9  1  0  0  0  0
 30 11  1  0  0  0  0
 26  2  1  0  0  0  0
  1 27  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 15  1  0  0  0  0
 21 22  1  0  0  0  0
  1 24  1  0  0  0  0
 25 17  1  0  0  0  0
 20 25  1  0  0  0  0
 24 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCCO)=CC(C(CO)CC2=CC(OC)=C(O)C=C2)=C1OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O11/c1-34-19-10-15(5-6-18(19)30)8-16(12-28)17-9-14(4-3-7-27)11-20(35-2)25(17)37-26-24(33)23(32)22(31)21(13-29)36-26/h5-6,9-11,16,21-24,26-33H,3-4,7-8,12-13H2,1-2H3

> <INCHI_KEY>
LEGVQDWMCXTVHB-UHFFFAOYSA-N

> <FORMULA>
C26H36O11

> <MOLECULAR_WEIGHT>
524.563

> <EXACT_MASS>
524.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.60561130450405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.21324155233333406

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.203582600655041

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.210123521936909

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416082316815

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
132.00099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-17         0                                  
HETATM    1  O   UNK     0    4665.3754667.073   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    4668.0404665.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4668.0404666.732   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.7124671.354   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4669.1184672.272   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4673.3774669.814   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    4669.3744664.419   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4670.7084665.192   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4662.7034665.192   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4661.3614664.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4665.3754660.569   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4664.0414659.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4662.7064660.569   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4661.3724659.797   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4660.0234667.092   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4658.6924667.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4665.3874670.127   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    4662.7064671.695   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    4660.0384670.154   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    4662.7064670.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4661.3734669.381   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4661.3734667.841   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    4662.7064667.071   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0    4664.0404667.841   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4664.0404669.381   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4666.7064664.420   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4665.3734665.189   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4664.0394664.419   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    4664.0394662.880   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    4665.3724662.110   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    4666.7064662.880   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    4672.0434669.042   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    4670.7104669.811   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    4669.3764669.042   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    4669.3764667.502   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    4670.7104666.732   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    4672.0434667.502   0.000  0.00  0.00           C+0
CONECT    1   27   24                                                       
CONECT    2    3    7   26                                                  
CONECT    3    2   35                                                       
CONECT    4    5   33                                                       
CONECT    5    4                                                            
CONECT    6   32                                                            
CONECT    7    2    8                                                       
CONECT    8    7                                                            
CONECT    9   10   28                                                       
CONECT   10    9                                                            
CONECT   11   12   30                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   16   22                                                       
CONECT   16   15                                                            
CONECT   17   25                                                            
CONECT   18   20                                                            
CONECT   19   21                                                            
CONECT   20   18   21   25                                                  
CONECT   21   19   20   22                                                  
CONECT   22   15   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24    1   25   23                                                  
CONECT   25   17   20   24                                                  
CONECT   26   27   31    2                                                  
CONECT   27   26   28    1                                                  
CONECT   28   27   29    9                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   11                                                  
CONECT   31   30   26                                                       
CONECT   32   33   37    6                                                  
CONECT   33   32   34    4                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36    3                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₁

Average Mass

524.5630 Da

Monoisotopic Mass

524.22576 Da

IUPAC Name

2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(CCCO)=CC(C(CO)CC2=CC(OC)=C(O)C=C2)=C1OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H36O11/c1-34-19-10-15(5-6-18(19)30)8-16(12-28)17-9-14(4-3-7-27)11-20(35-2)25(17)37-26-24(33)23(32)22(31)21(13-29)36-26/h5-6,9-11,16,21-24,26-33H,3-4,7-8,12-13H2,1-2H3

InChI Key

LEGVQDWMCXTVHB-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

Species Name	Source	Reference
Brainea insignis	LOTUS Database	35616633
Epimedium grandiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Lignan glycoside
Stilbene glycoside
Neolignan skeleton
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	0.45	ALOGPS
logP	0.21	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.21	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	132 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	3	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

14135390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0331069)

MOL for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0331069 (2-{2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]-4-(3-hydroxypropyl)-6-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)