NP-MRD: Showing NP-Card for 2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione (NP0325920)

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Record Information

Version

2.0

Created at

2022-09-12 07:02:59 UTC

Updated at

2022-09-12 07:03:00 UTC

NP-MRD ID

NP0325920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione

Description

2,5-Dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione 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). Based on a literature review very few articles have been published on 2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    6.4014   -0.7220   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1837   -0.8319   -1.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450   -0.5121   -0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    0.0390    0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893    0.3047    1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    0.3707    1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060    0.8961    2.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708    0.1201    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892    0.4979    1.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    1.0542    2.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2950    0.4626    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761    0.0777   -0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    0.2193   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183    0.7532    1.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6219    0.8461    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3689    0.4043   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6951   -0.1343   -1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3217   -0.2293   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4132   -0.4281   -0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -0.7266   -1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.7853   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -1.3150   -2.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4183   -1.3515    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1805   -1.1597   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248    0.3143   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -0.1177    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9531    0.9067    1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114   -0.3622   -1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.1239    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136    1.2765    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4495    0.4704   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466   -0.4967   -1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -0.6559   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.3091   -2.4472 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
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  3  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END


  Mrv1652309122209032D          

 22 23  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  8 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(=O)C(C(=O)C=CC2=CC=CC=C2)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-22-16-14(20)12(18)11(13(19)15(16)21)10(17)8-7-9-5-3-2-4-6-9/h2-8,18,21H,1H3

> <INCHI_KEY>
HYSJQRYYQGEYMY-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.36474971857006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione

> <JCHEM_LOGP>
1.8572687419999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.242009890917215

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.738975684132541

> <JCHEM_PKA_STRONGEST_BASIC>
-5.032298576257643

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
81.7238

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    8   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione

Traditional Name

2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=O)C(C(=O)C=CC2=CC=CC=C2)=C(O)C1=O

InChI Identifier

InChI=1S/C16H12O6/c1-22-16-14(20)12(18)11(13(19)15(16)21)10(17)8-7-9-5-3-2-4-6-9/h2-8,18,21H,1H3

InChI Key

HYSJQRYYQGEYMY-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, 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

Not Available

Chemical Taxonomy

Description

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
Cinnamic acid or derivatives
P-benzoquinone
Quinone
Styrene
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous ester
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Cyclic ketone
Enol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	1.86	ChemAxon
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.72 m³·mol⁻¹	ChemAxon
Polarizability	29.36 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

307229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

346344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione (NP0325920)

MOL for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

PDB for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

SMILES for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

INCHI for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

Structure for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0325920 (2,5-dihydroxy-3-methoxy-6-(3-phenylprop-2-enoyl)cyclohexa-2,5-diene-1,4-dione)