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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:55 UTC

Update Date

2023-02-21 17:25:04 UTC

HMDB ID

HMDB0036098

Secondary Accession Numbers

HMDB36098

Metabolite Identification

Common Name

Isoegomaketone

Description

Isoegomaketone belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group. Isoegomaketone has been detected, but not quantified in, fats and oils and herbs and spices. This could make isoegomaketone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Isoegomaketone.

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       6.394   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.727   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.061   4.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    9   12                                                       
CONECT    8    1    2    3                                                  
CONECT    9    5    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11   10                                                            
CONECT   12    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(Furan-3-yl)-4-methylpent-2-en-1-one	MeSH
1-(3-Furanyl)-4-methyl-2-penten-1-one	HMDB
1-(3-Furanyl)-4-methyl-2-penten-1-one, 9ci	HMDB
Isoegomaketone	MeSH

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

(2E)-1-(furan-3-yl)-4-methylpent-2-en-1-one

Traditional Name

(2E)-1-(furan-3-yl)-4-methylpent-2-en-1-one

CAS Registry Number

34348-59-9

SMILES

CC(C)\C=C\C(=O)C1=COC=C1

InChI Identifier

InChI=1S/C10H12O2/c1-8(2)3-4-10(11)9-5-6-12-7-9/h3-8H,1-2H3/b4-3+

InChI Key

XEYCZVQIOJGCNL-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl ketones

Alternative Parents

Substituents

Aryl ketone
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Furan
Enone
Acryloyl-group
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036098)
Cytoplasm (HMDB: HMDB0036098)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036098)

Source

Exogenous

Exogenous (HMDB: HMDB0036098)

Food

Food (HMDB: HMDB0036098)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0036098)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036098)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.55	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.44 m³·mol⁻¹	ChemAxon
Polarizability	18.14 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]+	142.832	30932474
DeepCCS	[M-H]-	140.12	30932474
DeepCCS	[M-2H]-	176.128	30932474
DeepCCS	[M+Na]+	151.582	30932474
AllCCS	[M+H]+	134.3	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	136.4	32859911
AllCCS	[M+Na-2H]-	137.4	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.98 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1764 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1892.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	582.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	366.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	590.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	713.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	164.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1301.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1375.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	497.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	565.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	42.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoegomaketone	CC(C)\C=C\C(=O)C1=COC=C1	1970.9	Standard polar	33892256
Isoegomaketone	CC(C)\C=C\C(=O)C1=COC=C1	1265.5	Standard non polar	33892256
Isoegomaketone	CC(C)\C=C\C(=O)C1=COC=C1	1282.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoegomaketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9700000000-e726bf7982edbebce1bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoegomaketone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoegomaketone 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 - Isoegomaketone 10V, Positive-QTOF	splash10-014i-1900000000-2ad1ba85057fac5b1c2a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 20V, Positive-QTOF	splash10-00kb-9800000000-cc3507a42ca695f772c5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 40V, Positive-QTOF	splash10-014i-9100000000-0ac9609bec5c8f097ea0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 10V, Negative-QTOF	splash10-03di-1900000000-ad0539cba92e5029e953	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 20V, Negative-QTOF	splash10-03xr-3900000000-affc168446a26ec81ac3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 40V, Negative-QTOF	splash10-014i-7900000000-822d73aac440aae02364	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 10V, Positive-QTOF	splash10-014i-5900000000-8ca9959806c87b9303fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 20V, Positive-QTOF	splash10-05oy-9100000000-43e7c213c560e9dcfaa2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 40V, Positive-QTOF	splash10-0002-9000000000-cdeb006e20aea95c17fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 10V, Negative-QTOF	splash10-03di-2900000000-6cc876087c2631ef9069	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 20V, Negative-QTOF	splash10-03xr-9800000000-c45a825a98960e1d651d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoegomaketone 40V, Negative-QTOF	splash10-014i-9100000000-4cdcd701e8b0f47a9144	2021-09-23	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB014938

KNApSAcK ID

C00010328

Chemspider ID

4477100

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318556

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isoegomaketone (HMDB0036098)

MOL for HMDB0036098 (Isoegomaketone)

3D MOL for HMDB0036098 (Isoegomaketone)

3D SDF for HMDB0036098 (Isoegomaketone)

3D-SDF for HMDB0036098 (Isoegomaketone)

PDB for HMDB0036098 (Isoegomaketone)

3D PDB for HMDB0036098 (Isoegomaketone)

SMILES for HMDB0036098 (Isoegomaketone)

INCHI for HMDB0036098 (Isoegomaketone)

Structure for HMDB0036098 (Isoegomaketone)

3D Structure for HMDB0036098 (Isoegomaketone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra