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Showing NP-Card for 1,4-Cyclohexanedione (NP0002765)

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Record Information
Version2.0
Created at2020-11-23 19:39:51 UTC
Updated at2021-08-19 23:59:20 UTC
NP-MRD IDNP0002765
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-Cyclohexanedione
Provided ByBMRBBMRB logo
DescriptionCyclohexane-1,4-dione is also known as 1,4-dioxocyclohexane or tetrahydroquinone. Cyclohexane-1,4-dione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 1,4-Cyclohexanedione was first documented in 2006 (PMID: 16504460). Based on a literature review very few articles have been published on cyclohexane-1,4-dione (PMID: 31995263) (PMID: 18794783) (PMID: 18642947).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002765 (1,4-Cyclohexanedione)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.0000   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121    2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  3  9  1  1
  3 10  1  0
  4 11  1  6
  4 12  1  0
  7 13  1  6
  7 14  1  0
  8 15  1  1
  8 16  1  0
M  END
Download

3D MOL for NP0002765 (1,4-Cyclohexanedione)

NP0002765
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.1214    2.4610    0.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    1.3300    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    0.6652   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -0.8509   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -1.1472    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -1.6877    1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111   -0.7488    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674    0.7357   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533    1.0436   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153    0.8475    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.1471   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490   -1.3981   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.9120    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.3303   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.8638   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    1.2752    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0002765 (1,4-Cyclohexanedione)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.0000   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121    2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -2.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  3  9  1  1
  3 10  1  0
  4 11  1  6
  4 12  1  0
  7 13  1  6
  7 14  1  0
  8 15  1  1
  8 16  1  0
M  END
> <DATABASE_ID>
NP0002765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2

> <INCHI_KEY>
DCZFGQYXRKMVFG-UHFFFAOYSA-N

> <FORMULA>
C6H8O2

> <MOLECULAR_WEIGHT>
112.128

> <EXACT_MASS>
112.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.295511454501474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
cyclohexane-1,4-dione

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.3089765393333333

> <ALOGPS_LOGS>
0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.151528513010472

> <JCHEM_PKA_STRONGEST_BASIC>
-7.061833859592316

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
28.8888

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-cyclohexanedione

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002765 (1,4-Cyclohexanedione)

NP0002765
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.1214    2.4610    0.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    1.3300    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    0.6652   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -0.8509   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -1.1472    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -1.6877    1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111   -0.7488    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674    0.7357   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533    1.0436   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153    0.8475    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.1471   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490   -1.3981   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.9120    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.3303   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.8638   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    1.2752    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
M  END
Download

PDB for NP0002765 (1,4-Cyclohexanedione)

HEADER    PROTEIN                                 11-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-17         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    2    4    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0002765 (1,4-Cyclohexanedione)

COMPND    NP0002765
HETATM    1  O1  UNL     1       0.121   2.461   0.540  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.049   1.330   0.068  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.350   0.665  -0.231  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.151  -0.851  -0.305  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.055  -1.147   0.649  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.344  -1.688   1.694  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.311  -0.749   0.228  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.267   0.736  -0.160  1.00  0.00           C  
HETATM    9  H1  UNL     1       1.753   1.044  -1.180  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.015   0.847   0.643  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.856  -1.147  -1.346  1.00  0.00           H  
HETATM   12  H4  UNL     1       2.049  -1.398  -0.041  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.077  -0.912   0.992  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.521  -1.330  -0.717  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.530   0.864  -1.242  1.00  0.00           H  
HETATM   16  H8  UNL     1      -2.038   1.275   0.407  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    9   10
CONECT    4    5   11   12
CONECT    5    6    6    7
CONECT    7    8   13   14
CONECT    8   15   16
END
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SMILES for NP0002765 (1,4-Cyclohexanedione)

O=C1CCC(=O)CC1
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INCHI for NP0002765 (1,4-Cyclohexanedione)

InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2
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View in JSmol
Synonyms
ValueSource
1,4-CyclohexanedioneChEBI
1,4-DioxocyclohexaneChEBI
TetrahydroquinoneChEBI
Chemical FormulaC6H8O2
Average Mass112.1280 Da
Monoisotopic Mass112.05243 Da
IUPAC Namecyclohexane-1,4-dione
Traditional Name1,4-cyclohexanedione
CAS Registry NumberNot Available
SMILES
O=C1CCC(=O)CC1
InChI Identifier
InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2
InChI KeyDCZFGQYXRKMVFG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Nicotiana bonariensisKNApSAcK Database
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point78.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point226.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility658200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.910 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.1ALOGPS
logP0.31ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)17.15ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.89 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0187593
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11995
KEGG Compound IDC08063
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,4-Cyclohexanedione
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28286
Good Scents IDrw1148601
References
General References
  1. Murakami K, Haneda M, Naruse M, Yoshino M: Prooxidant action of rhodizonic acid: transition metal-dependent generation of reactive oxygen species causing the formation of 8-hydroxy-2'-deoxyguanosine formation in DNA. Toxicol In Vitro. 2006 Sep;20(6):910-4. doi: 10.1016/j.tiv.2006.01.009. Epub 2006 Feb 28. [PubMed:16504460 ]
  2. Chao P, Chen H, Zhu Y, Lai H, Mo D, Zheng N, Chang X, Meng H, He F: A Benzo[1,2-b:4,5-c']Dithiophene-4,8-Dione-Based Polymer Donor Achieving an Efficiency Over 16. Adv Mater. 2020 Mar;32(10):e1907059. doi: 10.1002/adma.201907059. Epub 2020 Jan 29. [PubMed:31995263 ]
  3. Griesbeck AG, Hoinck LO, Lex J, Neudorfl J, Blunk D, El-Idreesy TT: 1,2,5,10,11,14-hexaoxadispiro[5.2.5.2]hexadecanes: novel spirofused bis-trioxane peroxides. Molecules. 2008 Aug 19;13(8):1743-58. doi: 10.3390/molecules13081743. [PubMed:18794783 ]
  4. Neumann MA: Tailor-made force fields for crystal-structure prediction. J Phys Chem B. 2008 Aug 14;112(32):9810-29. doi: 10.1021/jp710575h. Epub 2008 Jul 22. [PubMed:18642947 ]