NP-MRD: Showing NP-Card for Phillyrin (NP0138735)

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Record Information

Version

1.0

Created at

2022-06-29 18:33:48 UTC

Updated at

2022-06-29 18:33:48 UTC

NP-MRD ID

NP0138735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phillyrin

Description

UNII-VE9P4964MG, also known as phillyrin or forsythin, 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. Phillyrin is found in Bupleurum wenchuanense, Carex distachya, Eremophila racemosa, Forsythia europaea, Forsythia giraldiana, Forsythia intermedia, Forsythia koreana, Forsythia suspensa, Lancea tibetica, Osmanthus armatus, Osmanthus fortunei, Osmanthus fragrans, Phillyrea latifolia, Tinospora sinensis and Torreya fargesii. Based on a literature review very few articles have been published on UNII-VE9P4964MG.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292220332D          

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M  END

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 10 11  1  1  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  1  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 13 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 27 32  1  1  0  0  0
 26 33  1  6  0  0  0
 25 34  1  1  0  0  0
 19 35  1  0  0  0  0
 35 36  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C(C=C1)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22+,23-,24+,25-,26+,27+/m0/s1

> <INCHI_KEY>
KFFCKOBAHMGTMW-LGQRSHAYSA-N

> <FORMULA>
C27H34O11

> <MOLECULAR_WEIGHT>
534.558

> <EXACT_MASS>
534.210111915

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.78289055219788

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.1555855100000005

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196043729414313

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200014899680529

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
145.53

> <JCHEM_REFRACTIVITY>
131.72689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.040   6.949   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.466   6.629   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.942   5.164   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.449   4.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.924   3.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.388   2.555   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.088   4.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.775  -3.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.281  -3.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.757  -4.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.727  -6.116   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.220  -5.795   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.744  -4.331   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.203  -7.580   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.709  -7.900   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.185  -9.365   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.691  -9.685   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.722  -8.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.246  -7.076   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.739  -6.756   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.276  -5.932   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.783  -6.252   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.228  -8.861   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.167 -11.150   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.154 -10.510   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.264  -5.291   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.294  -4.147   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.479   5.988   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.003   7.453   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   16                                                  
CONECT   10    9   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    9                                                       
CONECT   17   13   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   35                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33   26                                                            
CONECT   34   25                                                            
CONECT   35   19   36                                                       
CONECT   36   35                                                            
CONECT   37    4   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Phillyrin	Kegg
Forsythin	MeSH
4-(4-(3,4-Dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl, (1S-(1alpha,3aalpha,4beta,6aalpha))-beta-D-glucopyranoside	MeSH

Chemical Formula

C₂₇H₃₄O₁₁

Average Mass

534.5580 Da

Monoisotopic Mass

534.21011 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

487-41-2

SMILES

COC1=C(OC)C=C(C=C1)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22+,23-,24+,25-,26+,27+/m0/s1

InChI Key

KFFCKOBAHMGTMW-LGQRSHAYSA-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
Bupleurum wenchuanense	LOTUS Database	35616633
Carex distachya	LOTUS Database	35616633
Eremophila racemosa	LOTUS Database	35616633
Forsythia europaea	LOTUS Database	35616633
Forsythia giraldiana	LOTUS Database	35616633
Forsythia intermedia	LOTUS Database	35616633
Forsythia koreana	LOTUS Database	35616633
Forsythia suspensa	LOTUS Database	35616633
Lancea tibetica	LOTUS Database	35616633
Osmanthus armatus	LOTUS Database	35616633
Osmanthus fortunei	LOTUS Database	35616633
Osmanthus fragrans	LOTUS Database	35616633
Phillyrea latifolia	LOTUS Database	35616633
Tinospora sinensis	LOTUS Database	35616633
Torreya fargesii var. yunnanensis	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
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Furofuran
Methoxybenzene
Anisole
Alkyl aryl ether
Fatty acyl
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glycoside (CHEBI:80888 )
lignan (CHEBI:80888 )
Lignan glycosides (C17048 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000648

Chemspider ID

91900

KEGG Compound ID

C17048

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phillyrin (NP0138735)

MOL for NP0138735 (Phillyrin)

3D MOL for NP0138735 (Phillyrin)

3D SDF for NP0138735 (Phillyrin)

3D-SDF for NP0138735 (Phillyrin)

PDB for NP0138735 (Phillyrin)

3D PDB for NP0138735 (Phillyrin)

SMILES for NP0138735 (Phillyrin)

INCHI for NP0138735 (Phillyrin)

Structure for NP0138735 (Phillyrin)

3D Structure for NP0138735 (Phillyrin)