NP-MRD: Showing NP-Card for isoeleutherin (NP0157969)

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Record Information

Version

2.0

Created at

2022-09-02 15:28:43 UTC

Updated at

2022-09-02 15:28:44 UTC

NP-MRD ID

NP0157969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoeleutherin

Description

(-)-Isoeleutherin 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. isoeleutherin is found in Eleutherine bulbosa and Sisyrinchium palmifolium. isoeleutherin was first documented in 2009 (PMID: 19862752). Based on a literature review a small amount of articles have been published on (-)-Isoeleutherin (PMID: 34401358) (PMID: 20835959) (PMID: 19445121) (PMID: 19350980).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.5616    1.9312    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019    1.5689    0.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305    0.2217    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951   -0.7546    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345   -2.0812    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240   -2.4710   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3234   -1.5093   -0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.1768    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133    0.8039    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008    2.0107    0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    0.3758   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.8947   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118   -1.3021   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726   -0.4124    0.2537 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8071   -0.5257   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    0.8917    0.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.3404   -0.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6173    2.5881    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0624   -1.9226   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -3.1386   -0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9597    1.2676    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788    2.9673    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    1.7261   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9235   -0.4589    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4223   -2.8208    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596   -3.4993   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071   -2.3480   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -1.3500   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -0.8638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051   -1.5980   -0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.1648   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930    0.0582   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    1.7217   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671    3.0901    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006    3.3566    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    2.3725    1.6705 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  2  0
  6  7  1  0
  7  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
  8  3  1  0
 17 11  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  1
 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
M  END


  Mrv1652309022217282D          

 20 22  0  0  1  0            999 V2000
    4.2868    2.4750    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
    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
   -0.7145   -0.4125    0.0000 C   0  0  0  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
    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
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  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
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 12 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0157969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1C(=O)C1=C(C[C@@H](C)O[C@@H]1C)C2=O

> <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-/m1/s1

> <INCHI_KEY>
IAJIIJBMBCZPSW-RKDXNWHRSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.3

> <EXACT_MASS>
272.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.7026426905898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R)-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>
52.6

> <JCHEM_REFRACTIVITY>
74.99249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19   12    7   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Isoeleutherin	MeSH

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.3000 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(=O)C1=C(C[C@@H](C)O[C@@H]1C)C2=O

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-/m1/s1

InChI Key

IAJIIJBMBCZPSW-RKDXNWHRSA-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
Eleutherine bulbosa	LOTUS Database	35616633
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
Phenol ether
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

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	2.23	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	28.7 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

C00029282

Chemspider ID

8621343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10445924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

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 ]
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 ]
Ganzera M, Nischang I, Siegl C, Senzenberger B, Svec F, Stuppner H: Application of MEKC and monolithic CEC for the analysis of bioactive naphthoquinones in Eleutherine americana. Electrophoresis. 2009 Nov;30(21):3757-63. doi: 10.1002/elps.200900247. [PubMed:19862752 ]
Liu XJ, Yan XQ, Wang NL: [Studies on chemical constituents of Eleutherine americana]. Zhong Yao Cai. 2009 Jan;32(1):55-8. [PubMed:19445121 ]
Ifesan BO, Hamtasin C, Mahabusarakam W, Voravuthikunchai SP: Assessment of antistaphylococcal activity of partially purified fractions and pure compounds from Eleutherine americana. J Food Prot. 2009 Feb;72(2):354-9. doi: 10.4315/0362-028x-72.2.354. [PubMed:19350980 ]
LOTUS database [Link]

Showing NP-Card for isoeleutherin (NP0157969)

MOL for NP0157969 (isoeleutherin)

3D MOL for NP0157969 (isoeleutherin)

3D SDF for NP0157969 (isoeleutherin)

3D-SDF for NP0157969 (isoeleutherin)

PDB for NP0157969 (isoeleutherin)

3D PDB for NP0157969 (isoeleutherin)

SMILES for NP0157969 (isoeleutherin)

INCHI for NP0157969 (isoeleutherin)

Structure for NP0157969 (isoeleutherin)

3D Structure for NP0157969 (isoeleutherin)