NP-MRD: Showing NP-Card for 1,8,9-Trihydroxy-3-methoxycoumestan (NP0051496)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:26 UTC

Updated at

2022-04-27 22:50:26 UTC

NP-MRD ID

NP0051496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,8,9-Trihydroxy-3-methoxycoumestan

Description

Wedelolactone belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, wedelolactone is considered to be a flavonoid. Wedelolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 1,8,9-Trihydroxy-3-methoxycoumestan is found in Aconitum kongboense, Eclipta alba , Eclipta prostrata, Hypericum erectum, Ougeinia dalbergioides , Thuja orientalis , Sphagneticola calendulacea and Wedelia calendulacea . 1,8,9-Trihydroxy-3-methoxycoumestan was first documented in 2021 (PMID: 34126350). Based on a literature review a significant number of articles have been published on Wedelolactone (PMID: 35337710) (PMID: 35255785) (PMID: 35203520) (PMID: 35182545) (PMID: 35047047) (PMID: 34984912).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.1402   -0.6303    0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3371    0.2395   -0.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502    0.1396   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665   -0.7379    0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762   -0.8465    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -1.7476    1.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799   -0.0224    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.8766   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476    0.9633   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905    1.6566   -1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    1.6275   -1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.4000   -2.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758    0.7752   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.4882   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4595    1.0036   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.5361   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469    1.0955   -0.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6386   -0.4530    0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8060   -0.9535    1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4564   -1.0039    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.5133    0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -0.7922    0.8952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1949   -0.0827    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896   -1.6853    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2026   -0.5366    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480   -0.3552    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9952   -1.3868    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216   -1.9248    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    1.6668   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4547    1.7839   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    0.8306   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7089   -0.6206    1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419   -1.7902    1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7 23  1  0
 23 13  2  0
 13 14  1  0
 14 21  2  0
 21 22  1  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  9  3  1  0
  8  7  1  0
 22 23  1  0
 15 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 20 33  1  0
 19 32  1  0
 17 31  1  0
 15 30  1  0
  9 29  1  0
M  END


  Mrv1652304282200502D          

 23 26  0  0  0  0            999 V2000
    5.1672    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -0.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016    1.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.0079    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
  3 21  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C3=C(C4=C(O3)C=C(O)C(O)=C4)C(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

> <INCHI_KEY>
XQDCKJKKMFWXGB-UHFFFAOYSA-N

> <FORMULA>
C16H10O7

> <MOLECULAR_WEIGHT>
314.249

> <EXACT_MASS>
314.042652662

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.381132205501746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
1.936084735

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.312350670809035

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.625310228138843

> <JCHEM_PKA_STRONGEST_BASIC>
-3.058423482916905

> <JCHEM_POLAR_SURFACE_AREA>
109.36000000000001

> <JCHEM_REFRACTIVITY>
78.0636

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.418  -1.805   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.036  -3.004   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.070   2.147   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.404   2.181   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.257  -0.895   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.723   3.521   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.183   0.594   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.028   1.881   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21    3                                                            
CONECT   22    1   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
1,8,9-Trihydroxy-3-methoxycoumestan	ChEBI

Chemical Formula

C₁₆H₁₀O₇

Average Mass

314.2490 Da

Monoisotopic Mass

314.04265 Da

IUPAC Name

3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

Traditional Name

3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C3=C(C4=C(O3)C=C(O)C(O)=C4)C(=O)OC2=C1

InChI Identifier

InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

InChI Key

XQDCKJKKMFWXGB-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aconitum kongboense	LOTUS Database	35616633
Eclipta alba	Plant	KNApSAcK
Eclipta prostrata	LOTUS Database	35616633
Hypericum erectum	LOTUS Database	35616633
Ougeinia dalbergioides	Plant	KNApSAcK
Platycladus orientalis	Plant	KNApSAcK
Sphagneticola calendulacea	LOTUS Database	35616633
Wedelia calendulacea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Furanocoumarin
Angular furanocoumarin
Coumarin
1-benzopyran
Benzopyran
Furopyran
Benzofuran
Anisole
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:10037 )
polyphenol (CHEBI:10037 )
delta-lactone (CHEBI:10037 )
coumestans (CHEBI:10037 )
Coumestan flavonoids (C10541 )
Coumestanes (C10541 )
Coumestan flavonoids (LMPK12090046 )

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	2.78	ALOGPS
logP	1.94	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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

HMDB0259891

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002585

Chemspider ID

4445124

KEGG Compound ID

C10541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Wedelolactone

METLIN ID

Not Available

PubChem Compound

5281813

PDB ID

Not Available

ChEBI ID

10037

Good Scents ID

Not Available

References

General References

Hioki T, Tokuda H, Kuroyanagi G, Kim W, Tachi J, Matsushima-Nishiwaki R, Iida H, Kozawa O: Olive polyphenols attenuate TNF-alpha-stimulated M-CSF and IL-6 synthesis in osteoblasts: Suppression of Akt and p44/p42 MAP kinase signaling pathways. Biomed Pharmacother. 2021 Jun 11;141:111816. doi: 10.1016/j.biopha.2021.111816. [PubMed:34126350 ]
Prakash T, Janadri S: Anti-inflammatory effect of wedelolactone on DSS induced colitis in rats: IL-6/STAT3 signaling pathway. J Ayurveda Integr Med. 2023 Mar-Apr;14(2):100544. doi: 10.1016/j.jaim.2022.100544. Epub 2022 Mar 22. [PubMed:35337710 ]
Zou YX, Mu ZQ, Wang J, Tian S, Li Y, Liu Y: Wedelolactone, a Component from Eclipta prostrata (L.) L., Inhibits the Proliferation and Migration of Head and Neck Squamous Cancer Cells through the AhR Pathway. Curr Pharm Biotechnol. 2022;23(15):1883-1892. doi: 10.2174/1389201023666220307110554. [PubMed:35255785 ]
Harkin K, Augustine J, Stitt AW, Xu H, Chen M: Wedelolactone Attenuates N-methyl-N-nitrosourea-Induced Retinal Neurodegeneration through Suppression of the AIM2/CASP11 Pathway. Biomedicines. 2022 Jan 28;10(2):311. doi: 10.3390/biomedicines10020311. [PubMed:35203520 ]
Wang SH, Cui LG, Su XL, Komal S, Ni RC, Zang MX, Zhang LR, Han SN: GSK-3beta-mediated activation of NLRP3 inflammasome leads to pyroptosis and apoptosis of rat cardiomyocytes and fibroblasts. Eur J Pharmacol. 2022 Apr 5;920:174830. doi: 10.1016/j.ejphar.2022.174830. Epub 2022 Feb 16. [PubMed:35182545 ]
Cai Z, Wang H, Jiang J, Xiao S, Xiao J, He J, Zhao Z, Yin J: Elaborate the Mechanism of Ancient Classic Prescriptions (Erzhi Formula) in Reversing GIOP by Network Pharmacology Coupled with Zebrafish Verification. Evid Based Complement Alternat Med. 2022 Jan 10;2022:7019792. doi: 10.1155/2022/7019792. eCollection 2022. [PubMed:35047047 ]
Wu Y, Pan B, Zhang Z, Li X, Leng Y, Ji Y, Sun K, Chen AF: Caspase-4/11-Mediated Pulmonary Artery Endothelial Cell Pyroptosis Contributes to Pulmonary Arterial Hypertension. Hypertension. 2022 Mar;79(3):536-548. doi: 10.1161/HYPERTENSIONAHA.121.17868. Epub 2022 Jan 5. [PubMed:34984912 ]
Sun X, Zhang H, Qin Q, Zhang X, Hou Y, Chen D, Su X, Jia M, Chen Y: Inhibitors of the MAPK/ NF-kappaB pathway attenuate the upregulation of the ET(B) receptor mediated by high glucose in vascular smooth muscle cells. Peptides. 2022 Apr;150:170732. doi: 10.1016/j.peptides.2021.170732. Epub 2021 Dec 29. [PubMed:34971676 ]
Maciel G, Lopes AA, Cantrell CL, de Castro Franca S, Bertoni BW, Lourenco MV: Jasmonates promote enhanced production of bioactive caffeoylquinic acid derivative in Eclipta prostrata (L.) L. hairy roots. Plant Cell Tissue Organ Cult. 2022;149(1-2):363-369. doi: 10.1007/s11240-021-02201-4. Epub 2021 Nov 22. [PubMed:34840370 ]
Yao E, Yang X, Huang X, Mi Y, Wu X, Fang M, Huang J, Qiu Y, Hong X, Peng L, Ren J, Huang R, Chen C, Yang L, Zhou Y, Zhuo R, Jin X, Zhao Y: Phytochemical wedelolactone reverses obesity by prompting adipose browning through SIRT1/AMPK/ PPARalpha pathway via targeting nicotinamide N-methyltransferase. Phytomedicine. 2022 Jan;94:153843. doi: 10.1016/j.phymed.2021.153843. Epub 2021 Nov 1. [PubMed:34785414 ]
Bhattacharyya S, Law S: Environmental pollutant N-N'ethylnitrosourea-induced leukemic NLRP3 inflammasome activation and its amelioration by Eclipta prostrata and its active compound wedelolactone. Environ Toxicol. 2022 Feb;37(2):322-334. doi: 10.1002/tox.23400. Epub 2021 Nov 2. [PubMed:34726823 ]
Ai Y, Shi W, Zuo X, Sun X, Chen Y, Wang Z, Li R, Song X, Dai W, Mu W, Ding K, Li Z, Li Q, Xiao X, Zhan X, Bai Z: Corrigendum: The Combination of Schisandrol B and Wedelolactone Synergistically Reverses Hepatic Fibrosis via Modulating Multiple Signaling Pathways in Mice. Front Pharmacol. 2021 Oct 7;12:777914. doi: 10.3389/fphar.2021.777914. eCollection 2021. [PubMed:34690790 ]
Wang G, Bi Y, Xiong H, Bo T, Han L, Zhou L, Zhang C, Zhang Y: Wedelolactone protects against cisplatin-induced nephrotoxicity in mice via inhibition of organic cation transporter 2. Hum Exp Toxicol. 2021 Dec;40(12_suppl):S447-S459. doi: 10.1177/09603271211047915. Epub 2021 Sep 30. [PubMed:34592875 ]
Xu S, Liu X, Liu X, Shi Y, Jin X, Zhang N, Li X, Zhang H: Wedelolactone ameliorates Pseudomonas aeruginosa-induced inflammation and corneal injury by suppressing caspase-4/5/11/GSDMD-mediated non-canonical pyroptosis. Exp Eye Res. 2021 Oct;211:108750. doi: 10.1016/j.exer.2021.108750. Epub 2021 Sep 2. [PubMed:34481822 ]
Pan B, Pan W, Lu Z, Xia C: Pharmacological Mechanisms Underlying the Hepatoprotective Effects of Ecliptae herba on Hepatocellular Carcinoma. Evid Based Complement Alternat Med. 2021 Jul 16;2021:5591402. doi: 10.1155/2021/5591402. eCollection 2021. [PubMed:34326886 ]
Fan R, Sui J, Dong X, Jing B, Gao Z: Wedelolactone alleviates acute pancreatitis and associated lung injury via GPX4 mediated suppression of pyroptosis and ferroptosis. Free Radic Biol Med. 2021 Sep;173:29-40. doi: 10.1016/j.freeradbiomed.2021.07.009. Epub 2021 Jul 8. [PubMed:34246777 ]
Tsai YT, Chen PY, To KY: Induction of Polyploidy and Metabolic Profiling in the Medicinal Herb Wedelia chinensis. Plants (Basel). 2021 Jun 17;10(6):1232. doi: 10.3390/plants10061232. [PubMed:34204356 ]
Ai Y, Shi W, Zuo X, Sun X, Chen Y, Wang Z, Li R, Song X, Dai W, Mu W, Ding K, Li Z, Li Q, Xiao X, Zhan X, Bai Z: The Combination of Schisandrol B and Wedelolactone Synergistically Reverses Hepatic Fibrosis Via Modulating Multiple Signaling Pathways in Mice. Front Pharmacol. 2021 Jun 3;12:655531. doi: 10.3389/fphar.2021.655531. eCollection 2021. [PubMed:34149411 ]
Sarwar S, Alamro AA, Alghamdi AA, Naeem K, Ullah S, Arif M, Yu JQ, Huq F: Enhanced Accumulation of Cisplatin in Ovarian Cancer Cells from Combination with Wedelolactone and Resulting Inhibition of Multiple Epigenetic Drivers. Drug Des Devel Ther. 2021 May 25;15:2211-2227. doi: 10.2147/DDDT.S288707. eCollection 2021. [PubMed:34079223 ]

Showing NP-Card for 1,8,9-Trihydroxy-3-methoxycoumestan (NP0051496)

MOL for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

3D MOL for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

3D SDF for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

3D-SDF for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

PDB for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

3D PDB for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

SMILES for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

INCHI for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

Structure for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)

3D Structure for NP0051496 (1,8,9-Trihydroxy-3-methoxycoumestan)