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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:15:26 UTC

Update Date

2023-02-21 17:25:32 UTC

HMDB ID

HMDB0037014

Secondary Accession Numbers

HMDB37014

Metabolite Identification

Common Name

gamma-Diosphenol

Description

gamma-Diosphenol, also known as γ-diosphenol, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on gamma-Diosphenol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    1    2    8                                                  
CONECT    7    3    4    9                                                  
CONECT    8    5    6   10                                                  
CONECT    9    7   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0037014
HETATM    1  C1  UNL     1      -2.690   1.043  -0.030  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.976  -0.214   0.454  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.689  -1.428   0.001  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.539  -0.173   0.236  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.187  -1.128  -0.330  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.462  -2.267  -0.756  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.624  -1.011  -0.511  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.258  -2.092  -0.686  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.313   0.298  -0.491  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.473   0.320   0.495  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.331   1.391  -0.267  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.213   1.033   0.678  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.188   1.386  -0.967  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.525   1.856   0.708  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.761   0.908  -0.136  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.138  -0.186   1.577  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.684  -1.629  -1.071  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.779  -1.280   0.270  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.402  -2.352   0.540  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.393  -2.682  -1.657  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.736   0.438  -1.529  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.144  -0.274   1.374  1.00  0.00           H  
HETATM   23  H11 UNL     1       4.347  -0.187  -0.007  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.709   1.370   0.744  1.00  0.00           H  
HETATM   25  H13 UNL     1       0.905   1.804  -1.224  1.00  0.00           H  
HETATM   26  H14 UNL     1       1.869   2.248   0.195  1.00  0.00           H  
HETATM   27  H15 UNL     1      -0.482   1.897   0.685  1.00  0.00           H  
HETATM   28  H16 UNL     1       0.598   0.912   1.703  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    6   20
CONECT    7    8    8    9
CONECT    9   10   11   21
CONECT   10   22   23   24
CONECT   11   12   25   26
CONECT   12   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
g-Diosphenol	Generator
Γ-diosphenol	Generator
2-Hydroxy-3-(isopropyl)-6-methylcyclohex-2-en-1-one	HMDB
2-Hydroxy-3-isopropyl-6-methyl-2-cyclohexen-1-one	HMDB
2-Hydroxy-6-methyl-3-(1-methylethyl)-2-cyclohexen-1-one	HMDB
2-Hydroxy-6-methyl-3-(1-methylethyl)-2-cyclohexen-1-one, 9ci	HMDB
Pseudodiosphenol	HMDB
Y-diosphenol	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

2-hydroxy-6-methyl-3-(propan-2-yl)cyclohex-2-en-1-one

Traditional Name

2-hydroxy-3-isopropyl-6-methylcyclohex-2-en-1-one

CAS Registry Number

54783-36-7

SMILES

CC(C)C1=C(O)C(=O)C(C)CC1

InChI Identifier

InChI=1S/C10H16O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h6-7,12H,4-5H2,1-3H3

InChI Key

POVACFJTDXZOQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037014)

Source

Endogenous

Endogenous (HMDB: HMDB0037014)

Animal

Animal (HMDB: HMDB0037014)

Exogenous

Food

Food (HMDB: HMDB0037014)

Exogenous (HMDB: HMDB0037014)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037014)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037014)

Lipid metabolism pathway (HMDB: HMDB0037014)

Cellular process

Cell signaling (HMDB: HMDB0037014)

Biochemical process

Lipid transport (HMDB: HMDB0037014)

Role

Biological role

Energy source (HMDB: HMDB0037014)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037014)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	34.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.59 g/L	ALOGPS
logP	1.59	ALOGPS
logP	2.49	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.31 m³·mol⁻¹	ChemAxon
Polarizability	18.98 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	143.706	30932474
DeepCCS	[M-H]-	141.114	30932474
DeepCCS	[M-2H]-	176.813	30932474
DeepCCS	[M+Na]+	151.824	30932474
AllCCS	[M+H]+	136.8	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	140.8	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	140.7	32859911
AllCCS	[M+Na-2H]-	142.1	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Diosphenol	CC(C)C1=C(O)C(=O)C(C)CC1	1824.5	Standard polar	33892256
gamma-Diosphenol	CC(C)C1=C(O)C(=O)C(C)CC1	1273.2	Standard non polar	33892256
gamma-Diosphenol	CC(C)C1=C(O)C(=O)C(C)CC1	1277.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Diosphenol,1TMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C)C(=O)C(C)CC1	1421.7	Semi standard non polar	33892256
gamma-Diosphenol,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)C(O)=C(C(C)C)CC1	1481.7	Semi standard non polar	33892256
gamma-Diosphenol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(C)C)CC1	1581.2	Semi standard non polar	33892256
gamma-Diosphenol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(C)C)CC1	1645.9	Standard non polar	33892256
gamma-Diosphenol,1TBDMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)CC1	1674.8	Semi standard non polar	33892256
gamma-Diosphenol,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C(C)C)CC1	1738.0	Semi standard non polar	33892256
gamma-Diosphenol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	2038.1	Semi standard non polar	33892256
gamma-Diosphenol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC1	2035.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Diosphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9400000000-3d9282e143be64e01dbf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Diosphenol GC-MS (1 TMS) - 70eV, Positive	splash10-0adj-9430000000-0b7c24c071daebd8fa55	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Diosphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 10V, Positive-QTOF	splash10-014i-1900000000-e591fdcf9409358f4b63	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 20V, Positive-QTOF	splash10-066r-9800000000-e0522475245388897234	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 40V, Positive-QTOF	splash10-0a4i-9000000000-756c18a2ed0d190e94f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 10V, Negative-QTOF	splash10-014i-0900000000-50f6d5168d37d0e2d8cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 20V, Negative-QTOF	splash10-014i-0900000000-e1e4d4639235c78a4782	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 40V, Negative-QTOF	splash10-100r-9800000000-5245e64276bbe5f719a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 20V, Negative-QTOF	splash10-014i-0900000000-23af486d3706a94c44f6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 40V, Negative-QTOF	splash10-0gba-9600000000-929ca1fb43695d265179	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 10V, Positive-QTOF	splash10-016r-1900000000-e7955c8dc66078559f51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 20V, Positive-QTOF	splash10-05q9-9600000000-270d5d3eb7309501d637	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Diosphenol 40V, Positive-QTOF	splash10-0036-9000000000-c985ad515f6e46677ce6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015992

KNApSAcK ID

C00010851

Chemspider ID

97326

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108261

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for gamma-Diosphenol (HMDB0037014)

MOL for HMDB0037014 (gamma-Diosphenol)

3D MOL for HMDB0037014 (gamma-Diosphenol)

3D SDF for HMDB0037014 (gamma-Diosphenol)

3D-SDF for HMDB0037014 (gamma-Diosphenol)

PDB for HMDB0037014 (gamma-Diosphenol)

3D PDB for HMDB0037014 (gamma-Diosphenol)

SMILES for HMDB0037014 (gamma-Diosphenol)

INCHI for HMDB0037014 (gamma-Diosphenol)

Structure for HMDB0037014 (gamma-Diosphenol)

3D Structure for HMDB0037014 (gamma-Diosphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra