NP-MRD: Showing NP-Card for 6-Ethyl-2,7-dimethoxyjuglone (NP0138212)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-31 17:15:57 UTC

Updated at

2025-12-20 01:41:07 UTC

NP-MRD ID

NP0138212

Natural Product DOI

https://doi.org/10.57994/4687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Ethyl-2,7-dimethoxyjuglone

Description

15254-86-1 Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 6-Ethyl-2,7-dimethoxyjuglone is found in Neofusicoccum australe and Neoscytalidium dimidiatum. 15254-86-1 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.9075   -1.4498   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251   -0.8430    0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614   -0.3303    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    0.9806    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264    1.9030    0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    3.2747    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    1.3787   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165    0.4736   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402   -0.8809    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514   -1.2969    0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -2.6066    0.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -1.8338   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749   -3.0823    0.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723   -1.3132   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349   -0.0312   -0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086    0.4350   -0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    0.2305   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726    0.9392   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    2.1704   -0.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4489   -2.3592   -0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6709   -0.7678   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -1.7732   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629   -0.1006    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0706   -1.6740    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343    3.5614   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078    3.7001    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    3.8180    0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    2.4384   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634   -3.4336    0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -2.0595   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.7080   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3393    0.6752    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7453   -0.8510    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  4  2  0
  4  5  1  0
  5  6  1  0
  8 18  1  0
 18 19  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 14  2  0
 14 12  1  0
 12 13  2  0
  4  3  1  0
 12  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
 11 29  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 14 30  1  0
M  END


  Mrv1533004251507492D          

 19 20  0  0  0  0            999 V2000
   -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  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(O)C2=C(C=C1OC)C(=O)C(OC)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-4-7-10(18-2)5-8-12(14(7)17)9(15)6-11(19-3)13(8)16/h5-6,17H,4H2,1-3H3

> <INCHI_KEY>
KRSHMRFACGPISX-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.261

> <EXACT_MASS>
262.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.511736541691807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-ethyl-5-hydroxy-2,7-dimethoxy-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.235241125666666

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.747418446249021

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50481900322596

> <JCHEM_PKA_STRONGEST_BASIC>
-4.595179304818226

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
70.9881

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-ethyl-5-hydroxy-2,7-dimethoxynaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₅

Average Mass

262.2610 Da

Monoisotopic Mass

262.08412 Da

IUPAC Name

6-ethyl-5-hydroxy-2,7-dimethoxy-1,4-dihydronaphthalene-1,4-dione

Traditional Name

6-ethyl-5-hydroxy-2,7-dimethoxynaphthalene-1,4-dione

CAS Registry Number

15254-86-1

SMILES

CCC1=C(O)C2=C(C=C1OC)C(=O)C(OC)=CC2=O

InChI Identifier

InChI=1S/C14H14O5/c1-4-7-10(18-2)5-8-12(14(7)17)9(15)6-11(19-3)13(8)16/h5-6,17H,4H2,1-3H3

InChI Key

KRSHMRFACGPISX-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	[email protected]	UNCG Oberlies Lab	Reema A. Al-Qiam	2025-10-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	UNCG Oberlies Lab	Reema A. Al-Qiam	2025-10-02	View Spectrum

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
Neofusicoccum australe	LOTUS Database	35616633
Neoscytalidium dimidiatum	LOTUS Database	35616633
Pyrenochaetopsis		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Anisole
Phenol ether
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous ester
Vinylogous acid
Ketone
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.68	ALOGPS
logP	2.24	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.99 m³·mol⁻¹	ChemAxon
Polarizability	26.51 Å³	ChemAxon
Number of Rings	2	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

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

15061180

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6-Ethyl-2,7-dimethoxyjuglone (NP0138212)

MOL for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

3D MOL for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

3D SDF for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

3D-SDF for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

PDB for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

3D PDB for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

SMILES for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

INCHI for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

Structure for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)

3D Structure for NP0138212 (6-Ethyl-2,7-dimethoxyjuglone)