NP-MRD: Showing NP-Card for malvone A (NP0030124)

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Record Information

Version

2.0

Created at

2021-06-19 21:33:55 UTC

Updated at

2021-06-29 23:57:55 UTC

NP-MRD ID

NP0030124

Secondary Accession Numbers

None

Natural Product Identification

Common Name

malvone A

Provided By

JEOL Database JEOL Logo

Description

malvone A is found in Aloe dawei and Malva sylvestris (family Malvaceae). malvone A was first documented in 2006 (Veshkurova, O., et al.). Based on a literature review a small amount of articles have been published on 5,6-dihydroxy-3-methoxy-2-methyl-1,4-dihydronaphthalene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123333D          

 27 28  0  0  0  0            999 V2000
   -1.5512    2.9251    0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    1.7909    0.9421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.6820   -0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450    0.4963   -0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -0.7385   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9638    0.3195   -2.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -0.7588   -2.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190    1.4741   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4939    1.3237   -3.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197    2.4026   -4.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    3.6202   -3.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    4.6738   -4.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022    3.7795   -2.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    5.0279   -1.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    2.7008   -1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551    2.8568   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496    3.9474   -0.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    2.6846    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315    3.7879    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    3.1629   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -1.0908   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770   -0.5740    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -1.5379   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349    0.3650   -4.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    2.2935   -5.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    5.4132   -3.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    4.9988   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
  8  6  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 16  1  0  0  0  0
 15  8  2  0  0  0  0
 16 17  2  0  0  0  0
  6  7  2  0  0  0  0
 10  9  2  0  0  0  0
 13 14  1  0  0  0  0
  9  8  1  0  0  0  0
 11 12  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
 15 13  1  0  0  0  0
  4  5  1  0  0  0  0
 13 11  2  0  0  0  0
  2  1  1  0  0  0  0
 10 25  1  0  0  0  0
  9 24  1  0  0  0  0
 14 27  1  0  0  0  0
 12 26  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END


  Mrv1652306192123333D          

 27 28  0  0  0  0            999 V2000
   -1.5512    2.9251    0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879    1.7909    0.9421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.6820   -0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450    0.4963   -0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -0.7385   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9638    0.3195   -2.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128   -0.7588   -2.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190    1.4741   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4939    1.3237   -3.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197    2.4026   -4.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    3.6202   -3.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    4.6738   -4.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022    3.7795   -2.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    5.0279   -1.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    2.7008   -1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551    2.8568   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496    3.9474   -0.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    2.6846    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315    3.7879    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    3.1629   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -1.0908   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770   -0.5740    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -1.5379   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349    0.3650   -4.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    2.2935   -5.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    5.4132   -3.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    4.9988   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
  8  6  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 16  1  0  0  0  0
 15  8  2  0  0  0  0
 16 17  2  0  0  0  0
  6  7  2  0  0  0  0
 10  9  2  0  0  0  0
 13 14  1  0  0  0  0
  9  8  1  0  0  0  0
 11 12  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
 15 13  1  0  0  0  0
  4  5  1  0  0  0  0
 13 11  2  0  0  0  0
  2  1  1  0  0  0  0
 10 25  1  0  0  0  0
  9 24  1  0  0  0  0
 14 27  1  0  0  0  0
 12 26  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030124

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C2=C(C([H])=C1[H])C(=O)C(=C(OC([H])([H])[H])C2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O5/c1-5-9(14)6-3-4-7(13)10(15)8(6)11(16)12(5)17-2/h3-4,13,15H,1-2H3

> <INCHI_KEY>
OIOGANSTEUPDQT-UHFFFAOYSA-N

> <FORMULA>
C12H10O5

> <MOLECULAR_WEIGHT>
234.207

> <EXACT_MASS>
234.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.50975117440376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-3-methoxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.5269075046666667

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.067875959721528

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.424096380040976

> <JCHEM_PKA_STRONGEST_BASIC>
-4.951835874781356

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
61.220700000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.551   2.925   0.979  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.688   1.791   0.942  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.072   1.682  -0.216  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.145   0.496  -0.843  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.580  -0.739  -0.386  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.964   0.320  -2.071  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.013  -0.759  -2.651  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.719   1.474  -2.586  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.494   1.324  -3.749  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.220   2.403  -4.255  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.167   3.620  -3.594  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.879   4.674  -4.090  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.402   3.780  -2.439  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.425   5.028  -1.866  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.669   2.701  -1.928  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.855   2.857  -0.713  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.850   3.947  -0.146  0.00  0.00           O+0
HETATM   18  H   UNK     0      -2.388   2.685   1.642  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.032   3.788   1.404  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.961   3.163  -0.009  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.262  -1.091  -1.167  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.177  -0.574   0.516  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.135  -1.538  -0.162  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.535   0.365  -4.265  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.821   2.293  -5.153  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.699   5.413  -3.473  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.866   4.999  -1.054  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    3    1                                                       
CONECT    3    4   16    2                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4   21   22   23                                             
CONECT    6    8    4    7                                                  
CONECT    7    6                                                            
CONECT    8    6   15    9                                                  
CONECT    9   10    8   24                                                  
CONECT   10    9   11   25                                                  
CONECT   11   12   10   13                                                  
CONECT   12   11   26                                                       
CONECT   13   14   15   11                                                  
CONECT   14   13   27                                                       
CONECT   15   16    8   13                                                  
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    5                                                            
CONECT   22    5                                                            
CONECT   23    5                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   12                                                            
CONECT   27   14                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀O₅

Average Mass

234.2070 Da

Monoisotopic Mass

234.05282 Da

IUPAC Name

5,6-dihydroxy-3-methoxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

5,6-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C2=C(C([H])=C1[H])C(=O)C(=C(OC([H])([H])[H])C2=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C12H10O5/c1-5-9(14)6-3-4-7(13)10(15)8(6)11(16)12(5)17-2/h3-4,13,15H,1-2H3

InChI Key

OIOGANSTEUPDQT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aloe dawei	Plant	KNApSAcK
Ancistrocladus abbreviatus	KNApSAcK Database	22123792
Malva sylvestris	JEOL database	Veshkurova, O., et al, Phytochemistry 67, 2376 (2006)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthoquinones. These 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
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous ester
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.14	ALOGPS
logP	1.53	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.22 m³·mol⁻¹	ChemAxon
Polarizability	22.51 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

C00034050

Chemspider ID

28283728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135542082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Veshkurova, O., et al. (2006). Veshkurova, O., et al, Phytochemistry 67, 2376 (2006). Phytochem..

Showing NP-Card for malvone A (NP0030124)

MOL for NP0030124 (malvone A)

3D MOL for NP0030124 (malvone A)

3D SDF for NP0030124 (malvone A)

3D-SDF for NP0030124 (malvone A)

PDB for NP0030124 (malvone A)

3D PDB for NP0030124 (malvone A)

SMILES for NP0030124 (malvone A)

INCHI for NP0030124 (malvone A)

Structure for NP0030124 (malvone A)

3D Structure for NP0030124 (malvone A)