NP-MRD: Showing NP-Card for Demethylwedelolactone (NP0056794)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 02:27:10 UTC

Updated at

2022-04-28 02:27:10 UTC

NP-MRD ID

NP0056794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylwedelolactone

Description

3,5,13,14-Tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one 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. Demethylwedelolactone is found in Eclipta alba , Eclipta prostrata , Hypericum erectum, Mnium hornum, Wedelia acapulcensis, Wedelia calendulacea and Wedelia chinensis. 3,5,13,14-Tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -0.4635    2.3382   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.5439   -1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552    1.5242   -0.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001    0.7349    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    0.7485    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2397   -0.0988    1.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5524   -0.0834    1.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -1.0120    2.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -1.0247    1.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384   -1.8935    2.2632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6349   -0.1694    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243   -0.2034    0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.9397    0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -0.6215   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935   -1.0475   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0230   -0.4922   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3334   -0.9540   -0.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6675    0.5003   -1.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    1.1098   -2.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3420    0.9425   -1.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    0.3992   -0.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    0.6632   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4950    1.4404    0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035    0.5617    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.6695    2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -2.5236    2.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -1.8384    0.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0335   -0.5730   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.9091   -2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047    1.7285   -2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 22  2  0
 22 21  1  0
 21 14  2  0
 14 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 22  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  4 11  1  0
 13 12  1  0
 20 21  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 15 27  1  0
 17 28  1  0
 19 29  1  0
 20 30  1  0
  5 23  1  0
M  END


  Mrv1652308211902372D          

 22 25  0  0  0  0            999 V2000
    7.1158    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0341    0.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948    1.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    0.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7281    1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105    0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632    0.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0158    1.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9342   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104    1.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6459    0.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    1.9223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    2.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -0.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    1.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578   -0.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  2  2  0  0  0  0
 12  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 15  2  0  0  0  0
 21 10  1  0  0  0  0
 21 14  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C3=C(C4=C(O3)C=C(O)C(O)=C4)C(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O7/c16-5-1-9(19)13-11(2-5)22-15(20)12-6-3-7(17)8(18)4-10(6)21-14(12)13/h1-4,16-19H

> <INCHI_KEY>
LUTYTNLPIUCKBJ-UHFFFAOYSA-N

> <FORMULA>
C15H8O7

> <MOLECULAR_WEIGHT>
300.222

> <EXACT_MASS>
300.027002598

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
28.226146471698875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.7901906789999995

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8555327572754345

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.596608983558839

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0651529299159446

> <JCHEM_POLAR_SURFACE_AREA>
120.36000000000001

> <JCHEM_REFRACTIVITY>
73.5813

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      13.283   3.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.130   0.801   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.737   0.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.590   3.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.975   2.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.032   1.471   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.368   1.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.295   2.883   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.745   3.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.959   3.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.593   0.889   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.518   1.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.900   2.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.363   2.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.211  -0.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.513   2.001   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.072   0.512   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.926   3.588   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      11.053   4.928   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.365  -1.598   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.399   3.554   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.748  -0.398   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    5   11                                                       
CONECT    3    6    7                                                       
CONECT    4    8   10                                                       
CONECT    5    1    2   16                                                  
CONECT    6    3   10   12                                                  
CONECT    7    3    8   17                                                  
CONECT    8    4    7   18                                                  
CONECT    9    1   13   19                                                  
CONECT   10    4    6   21                                                  
CONECT   11    2   13   22                                                  
CONECT   12    6   14   15                                                  
CONECT   13    9   11   14                                                  
CONECT   14   12   13   21                                                  
CONECT   15   12   20   22                                                  
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   15                                                            
CONECT   21   10   14                                                       
CONECT   22   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₈O₇

Average Mass

300.2220 Da

Monoisotopic Mass

300.02700 Da

IUPAC Name

3,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

Traditional Name

3,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C3=C(C4=C(O3)C=C(O)C(O)=C4)C(=O)OC2=C1

InChI Identifier

InChI=1S/C15H8O7/c16-5-1-9(19)13-11(2-5)22-15(20)12-6-3-7(17)8(18)4-10(6)21-14(12)13/h1-4,16-19H

InChI Key

LUTYTNLPIUCKBJ-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
Eclipta alba	Plant	KNApSAcK
Eclipta prostrata	Plant	KNApSAcK
Hypericum erectum	Plant	KNApSAcK
Mnium hornum	-	KNApSAcK
Wedelia acapulcensis	LOTUS Database	35616633
Wedelia calendulacea	Plant	KNApSAcK
Wedelia chinensis	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
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090041 )

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	2.31	ALOGPS
logP	1.79	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.6	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.58 m³·mol⁻¹	ChemAxon
Polarizability	28.23 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

HMDB0128455

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087310

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

5489605

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Demethylwedelolactone (NP0056794)

MOL for NP0056794 (Demethylwedelolactone)

3D MOL for NP0056794 (Demethylwedelolactone)

3D SDF for NP0056794 (Demethylwedelolactone)

3D-SDF for NP0056794 (Demethylwedelolactone)

PDB for NP0056794 (Demethylwedelolactone)

3D PDB for NP0056794 (Demethylwedelolactone)

SMILES for NP0056794 (Demethylwedelolactone)

INCHI for NP0056794 (Demethylwedelolactone)

Structure for NP0056794 (Demethylwedelolactone)

3D Structure for NP0056794 (Demethylwedelolactone)