NP-MRD: Showing NP-Card for 2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0142979)

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Record Information

Version

2.0

Created at

2022-09-01 21:38:53 UTC

Updated at

2022-09-01 21:38:53 UTC

NP-MRD ID

NP0142979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Symplocosin belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. 2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Abies nephrolepis, Acer truncatum, Arnica mollis, Arum italicum, Baccharis dracunculifolia, Balanophora japonica, Balanophora laxiflora, Berberis koreana, Brucea javanica, Carex distachya, Centaurea montana, Cistanche tubulosa, Clematis hexapetala, Daphne acutiloba, Daphne feddei, Daphne giraldii, Daphne oleoides, Epimedium sagittatum, Forsythia giraldiana, Forsythia intermedia, Forsythia koreana, Ipomoea nil, Macaranga tanarius, Narthecium asiaticum, Pedicularis densispica, Pinus massoniana, Prunus domestica, Rubus amabilis, Saussurea medusa, Sesamum indicum, Strychnos axillaris, Symplocos glomerata, Syringa reticulata, Tinospora sinensis and Vitex glabrata. Symplocosin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171503022D          

 37 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171503022D          

 37 41  0  0  0  0            999 V2000
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  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 18 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1OCC2C1COC2C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3

> <INCHI_KEY>
QLJNETOQFQXTLI-UHFFFAOYSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.035959056652565

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.009691453999999905

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202015174201058

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908521419511155

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
156.53

> <JCHEM_REFRACTIVITY>
127.24460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.93e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.633   6.683   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.079   4.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.555   2.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.802  -9.495   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.296  -9.175   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.266 -10.319   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.241  -9.999   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.717  -8.534   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.741 -11.784   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.711 -12.928   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.248 -12.104   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.724 -13.568   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.278 -10.959   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.785 -11.280   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
CONECT   34   21   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   18                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1OCC2C1COC2C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

InChI Identifier

InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3

InChI Key

QLJNETOQFQXTLI-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
Abies nephrolepis	LOTUS Database	35616633
Acer truncatum	LOTUS Database	35616633
Arnica mollis	LOTUS Database	35616633
Arum italicum	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Balanophora japonica	LOTUS Database	35616633
Balanophora laxiflora	LOTUS Database	35616633
Berberis koreana	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Carex distachya	LOTUS Database	35616633
Centaurea montana	LOTUS Database	35616633
Cistanche tubulosa	LOTUS Database	35616633
Clematis hexapetala	LOTUS Database	35616633
Daphne acutiloba	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Daphne giraldii	LOTUS Database	35616633
Daphne oleoides	LOTUS Database	35616633
Epimedium sagittatum	LOTUS Database	35616633
Forsythia giraldiana	LOTUS Database	35616633
Forsythia intermedia	LOTUS Database	35616633
Forsythia koreana	LOTUS Database	35616633
Ipomoea nil	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Narthecium asiaticum	LOTUS Database	35616633
Pedicularis densispica	LOTUS Database	35616633
Pinus massoniana	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Rubus amabilis	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Sesamum indicum	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633
Symplocos glomerata	LOTUS Database	35616633
Syringa reticulata	LOTUS Database	35616633
Tinospora sinensis	LOTUS Database	35616633
Vitex glabrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Methoxybenzene
Furofuran
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Dialkyl ether
Ether
Acetal
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
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	0.93	ALOGPS
logP	0.0097	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.24 m³·mol⁻¹	ChemAxon
Polarizability	53.04 Å³	ChemAxon
Number of Rings	5	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

5351523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0142979)

MOL for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0142979 (2-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)