NP-MRD: Showing NP-Card for 2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione (NP0246683)

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Record Information

Version

2.0

Created at

2022-09-07 08:14:04 UTC

Updated at

2022-09-07 08:14:04 UTC

NP-MRD ID

NP0246683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione

Description

2,6-Di-tert-butylbenzoquinone, also known as DBQ, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. 2,6-Di-tert-butylbenzoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione is found in Leptolyngbya tenuis. Detected in tapwater as presumed oxidant of 2,6-Di-tert-butyl-4-methylphenol HCH42-H.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    3.5917   -0.8427   -0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329    0.0717   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664    0.3058    1.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696    1.4145   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -0.4786   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -1.6408   -0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383   -2.2404   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -3.3588   -1.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -1.5771   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3408   -0.4185   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5216    0.3042    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8168   -0.4151    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440    0.6626    1.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798    1.6259   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    0.1826    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922    1.2875    0.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -0.9819   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.4199   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035   -1.8357   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4960    1.2823    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -0.5431    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    0.3745    1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    1.7652   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    2.1894   -0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3281    1.3293   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -2.2069   -1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -1.9797   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354   -0.4811   -1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539   -1.4235    0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806    0.0831    0.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029    1.7456    1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    0.3715    2.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771    0.1398    2.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277    1.9445   -0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2336    1.4100   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342    2.3537    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 15  1  0
 15 16  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 15  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv1652303102016542D          

 16 16  0  0  0  0            999 V2000
    1.1134   -0.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    1.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -1.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -1.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    1.2368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    1.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  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
M  END
> <DATABASE_ID>
NP0246683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C)C1=CC(=O)C=C(C1=O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8H,1-6H3

> <INCHI_KEY>
RDQSIADLBQFVMY-UHFFFAOYSA-N

> <FORMULA>
C14H20O2

> <MOLECULAR_WEIGHT>
220.3074

> <EXACT_MASS>
220.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.279663025105734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.878484552666668

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.136462153060856

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
66.99239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0       2.078  -0.769   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.692   0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.692  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.924   0.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.310   3.387   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.924   2.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.308   3.849   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.002   1.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.846  -2.617   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.692  -2.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.232  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.846  -3.849   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.310   2.309   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.924   1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.692   2.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.692   1.539   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3   14                                                       
CONECT    5    6                                                            
CONECT    6    5    7    8   16                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10                                                            
CONECT   10    3    9   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   14                                                            
CONECT   14    4   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    2    6   15                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2, 6-Di-tert-butyl-p-benzoquinone	HMDB
2, 6-Di-tert-butylquinone	HMDB
2,6-Bis(1, 1-dimethylethyl)-2,5-cyclohexadiene-1,4-dione	HMDB
2,6-Bis(1,1-dimethylethyl)-2,5-cyclohexadiene-1,4-dione	HMDB
2,6-Bis-(1,1-dimethylethyl)-2,5-cycloxehadien-1,4-dione	HMDB
2,6-Bis-tert-butylbenzoquinone	HMDB
2,6-Di-t-butyl-p-benzoquinone	HMDB
2,6-Di-tert-butyl-1,4-benzoquinone	HMDB
2,6-Di-tert-butyl-p-benzoquinone	HMDB
2,6-Di-tert-butyl-para-benzoquinone	HMDB
2,6-Di-tert-butylquinone	HMDB
2,6-Ditert-butylbenzo-1,4-quinone (acd/name 4.0)	HMDB
Benzoquinone, 2,6-di-(1,1-dimethylethyl)	HMDB
DBQ	HMDB
p-Benzoquinone, 2,6-bis-(1,1-dimethylethyl)	HMDB
2,6-Di-tert-butyl-4-benzoquinone	MeSH
BHT-Quinone	MeSH

Chemical Formula

C₁₄H₂₀O₂

Average Mass

220.3074 Da

Monoisotopic Mass

220.14633 Da

IUPAC Name

2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C)C1=CC(=O)C=C(C1=O)C(C)(C)C

InChI Identifier

InChI=1S/C14H20O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8H,1-6H3

InChI Key

RDQSIADLBQFVMY-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

Species Name	Source	Reference
Leptolyngbya tenuis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Quinone
P-benzoquinone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.79	ALOGPS
logP	3.88	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-8.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.99 m³·mol⁻¹	ChemAxon
Polarizability	25.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013817

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000860

KNApSAcK ID

Not Available

Chemspider ID

12336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione (NP0246683)

MOL for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

PDB for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

SMILES for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

INCHI for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

Structure for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0246683 (2,6-di-tert-butylcyclohexa-2,5-diene-1,4-dione)