NP-MRD: Showing NP-Card for (+)-Phillygenin (NP0050441)

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Record Information

Version

2.0

Created at

2022-04-27 21:39:28 UTC

Updated at

2022-04-27 21:39:28 UTC

NP-MRD ID

NP0050441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Phillygenin

Description

PHILLYGENIN belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (+)-Phillygenin is found in Anisacanthus virgularis, Aristolochia flos-avis, Bupleurum wenchuanense, Chionanthus retusus, Chionanthus virginica, Forsythia europaea, Forsythia giraldiana, Forsythia intermedia, Forsythia japonica, Forsythia koreana, Forsythia suspensa , Forsythia viridissima, Lancea tibetica, Lindera praecox, Magnolia biondii, Magnolia coco, Magnolia fargesii , Magnolia kobus var. borealis , Orophea enneandra, Osmanthus aquifolium, Osmanthus asiaticus, Osmanthus fragrans , Otoba parvifolia , Persea kurzii, Phillyrea latifolia , Piper sylvaticum and Virola michelii . (+)-Phillygenin was first documented in 2021 (PMID: 34899295). Based on a literature review a small amount of articles have been published on PHILLYGENIN (PMID: 35421804) (PMID: 35405527) (PMID: 35340247) (PMID: 35194875).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223392D          

 27 30  0  0  1  0            999 V2000
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -4.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  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  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1652304272223392D          

 27 30  0  0  1  0            999 V2000
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -4.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  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  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m0/s1

> <INCHI_KEY>
CPJKKWDCUOOTEW-YJPXFSGGSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.417

> <EXACT_MASS>
372.157288493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.06790392004085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.4236536033333334

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.910746793682316

> <JCHEM_PKA_STRONGEST_BASIC>
-3.769691453217552

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
99.58250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+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      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.296  -9.175   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.615   4.898   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.410   6.179   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₆

Average Mass

372.4170 Da

Monoisotopic Mass

372.15729 Da

IUPAC Name

4-[(1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

Traditional Name

4-[(1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m0/s1

InChI Key

CPJKKWDCUOOTEW-YJPXFSGGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anisacanthus virgularis	Plant	KNApSAcK
Aristolochia flos-avis	Plant	KNApSAcK
Bupleurum wenchuanense	Plant	KNApSAcK
Chionanthus retusus	Plant	KNApSAcK
Chionanthus virginica	Plant	KNApSAcK
Forsythia europaea	Plant	KNApSAcK
Forsythia giraldiana	Plant	KNApSAcK
Forsythia intermedia	Plant	KNApSAcK
Forsythia japonica	Plant	KNApSAcK
Forsythia koreana	Plant	KNApSAcK
Forsythia suspensa	Plant	KNApSAcK
Forsythia viridissima	Plant	KNApSAcK
Lancea tibetica	Plant	KNApSAcK
Lindera praecox	Plant	KNApSAcK
Magnolia biondii	LOTUS Database	35616633
Magnolia coco	LOTUS Database	35616633
Magnolia fargesii	Plant	KNApSAcK
Magnolia kobus var. borealis	Plant	KNApSAcK
Orophea enneandra	Plant	KNApSAcK
Osmanthus aquifolium	Plant	KNApSAcK
Osmanthus asiaticus	Plant	KNApSAcK
Osmanthus fragrans	Plant	KNApSAcK
Otoba parvifolia	Plant	KNApSAcK
Persea kurzii	Plant	KNApSAcK
Phillyrea latifolia	Plant	KNApSAcK
Piper sylvaticum	LOTUS Database	35616633
Virola michelii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Furofuran
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxolane
Ether
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	2.83	ALOGPS
logP	2.42	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.58 m³·mol⁻¹	ChemAxon
Polarizability	39.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000647

Chemspider ID

2340771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083590

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Feng H, Zhang J, Zhang K, Wang X, Zhang K, Guo Z, Han S, Wang L, Qiu Z, Wang G, Li J: Phillygenin activates PKR/eIF2alpha pathway and induces stress granule to exert anti-avian infectious bronchitis virus. Int Immunopharmacol. 2022 Jul;108:108764. doi: 10.1016/j.intimp.2022.108764. Epub 2022 Apr 11. [PubMed:35421804 ]
Guo J, Yan WR, Tang JK, Jin X, Xue HH, Wang T, Zhang LW, Sun QY, Liang ZX: Dietary phillygenin supplementation ameliorates aflatoxin B1-induced oxidative stress, inflammation, and apoptosis in chicken liver. Ecotoxicol Environ Saf. 2022 May 1;236:113481. doi: 10.1016/j.ecoenv.2022.113481. Epub 2022 Apr 8. [PubMed:35405527 ]
Feng H, He L, Wang Z, Pi B, Liu Z: Phillygenin Protects the Intestinal Barrier from Dysfunction via let-7b Signaling Pathway and Regulation of Intestinal Microbiota. J Healthc Eng. 2022 Mar 16;2022:4769709. doi: 10.1155/2022/4769709. eCollection 2022. [PubMed:35340247 ]
Pan MH, Su YF, Liu XJ, Xiang SQ, Ding YX, Li Q: Identification of Forsythia suspensa (Thunb.) Vahl in different harvest periods using intelligent sensory technologies, HPLC characteristic fingerprint coupled with chemometrics. Phytochem Anal. 2022 Apr;33(3):490-501. doi: 10.1002/pca.3104. Epub 2022 Feb 22. [PubMed:35194875 ]
Qu Q, Li Y, Dong Q, Li S, Du H, Wang Z, Gong X, Zhang W, Lv W, Chao L, Liu M, Tang X, Guo S: Comparative Evaluation of Forsythiae Fructus From Different Harvest Seasons and Regions by HPLC/NIR Analysis and Anti-inflammatory and Antioxidant Assays. Front Pharmacol. 2021 Nov 24;12:737576. doi: 10.3389/fphar.2021.737576. eCollection 2021. [PubMed:34899295 ]

Showing NP-Card for (+)-Phillygenin (NP0050441)

MOL for NP0050441 ((+)-Phillygenin)

3D MOL for NP0050441 ((+)-Phillygenin)

3D SDF for NP0050441 ((+)-Phillygenin)

3D-SDF for NP0050441 ((+)-Phillygenin)

PDB for NP0050441 ((+)-Phillygenin)

3D PDB for NP0050441 ((+)-Phillygenin)

SMILES for NP0050441 ((+)-Phillygenin)

INCHI for NP0050441 ((+)-Phillygenin)

Structure for NP0050441 ((+)-Phillygenin)

3D Structure for NP0050441 ((+)-Phillygenin)