NP-MRD: Showing NP-Card for (+)-Eleutherin (NP0051612)

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Record Information

Version

1.0

Created at

2022-04-27 22:54:43 UTC

Updated at

2022-04-27 22:54:43 UTC

NP-MRD ID

NP0051612

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Eleutherin

Description

Eleutherin belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. (+)-Eleutherin is found in Eleutherine americana MERR.et HEYNE , Eleutherine bulbosa and Sisyrinchium palmifolium. It was first documented in 2008 (PMID: 18758108). Based on a literature review a significant number of articles have been published on Eleutherin (PMID: 34401358) (PMID: 24436995) (PMID: 20835959) (PMID: 20155402) (PMID: 19862752) (PMID: 19783445).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.5123    1.6007   -1.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666    1.2702   -1.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251    0.1062   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9378   -0.7276    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.8755    0.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619   -2.1759    1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.3306    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5933   -0.1797   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145    0.6963   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    1.7391   -1.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654    0.3782   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1120   -0.7225    0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -1.0078    0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053   -0.5487   -0.4698 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7742   -0.8533   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863    0.8089   -0.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9208    1.2981   -0.6836 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8714    2.6427    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581   -1.6173    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177   -2.6707    1.6018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5479    2.4438   -2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0472    0.7128   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0507    1.9695   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772   -0.4679   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4459   -2.5499    1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0867   -3.0635    1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8303   -0.3155    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -2.0625    1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -1.1275   -1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -0.1589    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -1.9199    0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3960   -0.6711   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7060    1.5026   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    3.1619   -0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904    3.2400   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7205    2.4752    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  2  0
 19  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7  8  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  6
 18 34  1  0
 18 35  1  0
 18 36  1  0
  6 26  1  0
  5 25  1  0
  4 24  1  0
M  END


  Mrv1652304282200542D          

 20 22  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 16 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C3=C(C[C@H](C)O[C@@H]3C)C(=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-8-7-11-13(9(2)20-8)16(18)14-10(15(11)17)5-4-6-12(14)19-3/h4-6,8-9H,7H2,1-3H3/t8-,9+/m0/s1

> <INCHI_KEY>
IAJIIJBMBCZPSW-DTWKUNHWSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.3

> <EXACT_MASS>
272.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.384915234680907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S)-9-methoxy-1,3-dimethyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.8497201770000002

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.115536783262211

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
74.9925

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eleutherin

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1R,3S)-9-Methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo(g)isochromene-5,10-dione	MeSH

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.3000 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

(1R,3S)-9-methoxy-1,3-dimethyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

Traditional Name

eleutherin

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(C[C@H](C)O[C@@H]3C)C(=O)C2=CC=C1

InChI Identifier

InChI=1S/C16H16O4/c1-8-7-11-13(9(2)20-8)16(18)14-10(15(11)17)5-4-6-12(14)19-3/h4-6,8-9H,7H2,1-3H3/t8-,9+/m0/s1

InChI Key

IAJIIJBMBCZPSW-DTWKUNHWSA-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
Eleutherine americana MERR.et HEYNE	Plant	KNApSAcK
Eleutherine bulbosa	Plant	KNApSAcK
Sisyrinchium palmifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzoisochromanequinone (CHEBI:4774 )

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	2.23	ALOGPS
logP	1.85	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.99 m³·mol⁻¹	ChemAxon
Polarizability	28.38 Å³	ChemAxon
Number of Rings	3	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

C00002821

Chemspider ID

9760

KEGG Compound ID

C10340

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1546911

References

General References

Quadros Gomes AR, da Rocha Galucio NC, de Albuquerque KCO, Brigido HPC, Varela ELP, Castro ALG, Vale VV, Bahia MO, Rodriguez Burbano RM, de Molfeta FA, Carneiro LA, Percario S, Dolabela MF: Toxicity evaluation of Eleutherine plicata Herb. extracts and possible cell death mechanism. Toxicol Rep. 2021 Jul 31;8:1480-1487. doi: 10.1016/j.toxrep.2021.07.015. eCollection 2021. [PubMed:34401358 ]
Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA: Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions. Bioorg Med Chem. 2013 Dec 15;21(24):7971-80. doi: 10.1016/j.bmc.2013.09.052. [PubMed:24436995 ]
Gallo FR, Palazzino G, Federici E, Iurilli R, Galeffi C, Chifundera K, Nicoletti M: Polyketides from Eleutherine bulbosa. Nat Prod Res. 2010 Oct;24(16):1578-86. doi: 10.1080/14786419.2010.500007. [PubMed:20835959 ]
Kusuma IW, Arung ET, Rosamah E, Purwatiningsih S, Kuspradini H, Syafrizal, Astuti J, Kim YU, Shimizu K: Antidermatophyte and antimelanogenesis compound from Eleutherine americana grown in Indonesia. J Nat Med. 2010 Apr;64(2):223-6. doi: 10.1007/s11418-010-0396-7. Epub 2010 Feb 13. [PubMed:20155402 ]
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Showing NP-Card for (+)-Eleutherin (NP0051612)

MOL for NP0051612 ((+)-Eleutherin)

3D MOL for NP0051612 ((+)-Eleutherin)

3D SDF for NP0051612 ((+)-Eleutherin)

3D-SDF for NP0051612 ((+)-Eleutherin)

PDB for NP0051612 ((+)-Eleutherin)

3D PDB for NP0051612 ((+)-Eleutherin)

SMILES for NP0051612 ((+)-Eleutherin)

INCHI for NP0051612 ((+)-Eleutherin)

Structure for NP0051612 ((+)-Eleutherin)

3D Structure for NP0051612 ((+)-Eleutherin)