NP-MRD: Showing NP-Card for Fumiquinone A (NP0007167)

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Record Information

Version

2.0

Created at

2020-12-09 04:02:07 UTC

Updated at

2021-07-15 16:56:51 UTC

NP-MRD ID

NP0007167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fumiquinone A

Provided By

NPAtlas

Description

Fumiquinone A is found in Aspergillus fumigatus. Based on a literature review very few articles have been published on Fumiquinone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118383D          

 32 32  0  0  0  0            999 V2000
   -3.3478    3.0753   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.9306   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    0.8018   -0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245   -0.2322   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5860   -0.1708    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373   -1.3992    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -2.3972    0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.3478    3.0753   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.9306   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2245   -0.2322   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4373   -1.3992    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -2.3972    0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1936   -2.6167    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9187    0.4634    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118383D          

 32 32  0  0  0  0            999 V2000
   -3.3478    3.0753   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.9306   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    0.8018   -0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245   -0.2322   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5860   -0.1708    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373   -1.3992    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -2.3972    0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -1.4602    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7031    0.6344   -0.0914 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0007167

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O6/c1-6-8(4-5-18-7(2)13)10(15)12(17-3)11(16)9(6)14/h16H,4-5H2,1-3H3

> <INCHI_KEY>
HMEZWNGVEQMXAZ-UHFFFAOYSA-N

> <FORMULA>
C12H14O6

> <MOLECULAR_WEIGHT>
254.238

> <EXACT_MASS>
254.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.971748058374803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl acetate

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
0.3397422753333335

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.506473936327112

> <JCHEM_PKA_STRONGEST_BASIC>
-5.014201220528122

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
64.1102

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxy-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.3478    3.0753   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9187    0.4634    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.348   3.075  -0.188  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.407   1.931  -1.016  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.665   0.802  -0.646  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.224  -0.232  -0.053  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.586  -0.171   0.200  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.437  -1.399   0.325  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.989  -2.397   0.900  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.007  -1.460   0.058  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.194  -2.617   0.424  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.437  -0.421  -0.540  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.000  -0.465  -0.817  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.703   0.634  -0.091  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.086   0.691  -0.280  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.972  -0.318   0.055  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.447  -0.182  -0.182  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.491  -1.363   0.569  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.215   0.748  -0.921  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.736   1.755  -1.486  0.00  0.00           O+0
HETATM   19  H   UNK     0      -3.716   2.782   0.813  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.280   3.423  -0.122  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.986   3.868  -0.614  0.00  0.00           H+0
HETATM   22  H   UNK     0      -5.173   0.218  -0.548  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.058  -3.221  -0.487  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.834  -3.308   1.046  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.685  -2.393   1.047  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.472  -1.430  -0.571  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.139  -0.294  -1.926  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.305   1.636  -0.409  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.415   0.557   0.981  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.883  -1.186  -0.086  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.661   0.275  -1.166  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.919   0.463   0.595  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   22                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8   23   24   25                                             
CONECT   10    8   11   17                                                  
CONECT   11   10   12   26   27                                             
CONECT   12   11   13   28   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   30   31   32                                             
CONECT   16   14                                                            
CONECT   17   10   18    3                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   12                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

RDKit          3D

32 32  0  0  0  0  0  0  0  0999 V2000
   -3.3478    3.0753   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.9306   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    0.8018   -0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245   -0.2322   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5860   -0.1708    0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373   -1.3992    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -2.3972    0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -1.4602    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936   -2.6167    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4366   -0.4210   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001   -0.4652   -0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031    0.6344   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861    0.6905   -0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721   -0.3184    0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4465   -0.1819   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907   -1.3628    0.5688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    0.7478   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    1.7549   -1.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    2.7816    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803    3.4231   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862    3.8681   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1726    0.2175   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582   -3.2206   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -3.3079    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -2.3929    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -1.4302   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -0.2941   -1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049    1.6357   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4148    0.5573    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8830   -1.1855   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607    0.2745   -1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187    0.4634    0.5950 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 10 17  1  0
 17 18  2  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-(4-Hydroxy-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl acetic acid	Generator

Chemical Formula

C₁₂H₁₄O₆

Average Mass

254.2380 Da

Monoisotopic Mass

254.07904 Da

IUPAC Name

2-(4-hydroxy-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl acetate

Traditional Name

2-(4-hydroxy-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=O)C(C)=C(CCOC(C)=O)C1=O

InChI Identifier

InChI=1S/C12H14O6/c1-6-8(4-5-18-7(2)13)10(15)12(17-3)11(16)9(6)14/h16H,4-5H2,1-3H3

InChI Key

HMEZWNGVEQMXAZ-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
Aspergillus fumigatus	NPAtlas	17617730

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinones

Alternative Parents

Substituents

Ubiquinone skeleton
P-benzoquinone
Quinone
Vinylogous acid
Vinylogous ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	0.49	ALOGPS
logP	0.34	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	5.51	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.11 m³·mol⁻¹	ChemAxon
Polarizability	24.97 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA007233

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28284243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136773314

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Fumiquinone A (NP0007167)

MOL for NP0007167 (Fumiquinone A)

3D MOL for NP0007167 (Fumiquinone A)

3D SDF for NP0007167 (Fumiquinone A)

3D-SDF for NP0007167 (Fumiquinone A)

PDB for NP0007167 (Fumiquinone A)

3D PDB for NP0007167 (Fumiquinone A)

SMILES for NP0007167 (Fumiquinone A)

INCHI for NP0007167 (Fumiquinone A)

Structure for NP0007167 (Fumiquinone A)

3D Structure for NP0007167 (Fumiquinone A)