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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:23:37 UTC

Update Date

2023-02-21 17:24:48 UTC

HMDB ID

HMDB0035414

Secondary Accession Numbers

HMDB35414

Metabolite Identification

Common Name

Lepalone

Description

Lepalone belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom. Lepalone has been detected, but not quantified in, herbs and spices and roman camomiles (Chamaemelum nobile). This could make lepalone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lepalone.

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       2.916   4.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.582   2.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.419   4.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.159   4.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.190   3.459   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.913   2.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.582   3.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.752   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.249   4.747   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.249   6.287   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.420   2.125   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    9   12                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3    5    7                                                  
CONECT   10    4    8   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
5-(3-Furyl)-2-methyl-1-penten-3-one	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

5-(furan-3-yl)-2-methylpent-1-en-3-one

Traditional Name

5-(furan-3-yl)-2-methylpent-1-en-3-one

CAS Registry Number

80445-58-5

SMILES

CC(=C)C(=O)CCC1=COC=C1

InChI Identifier

InChI=1S/C10H12O2/c1-8(2)10(11)4-3-9-5-6-12-7-9/h5-7H,1,3-4H2,2H3

InChI Key

XUCQQLCBOJJVRF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-branched alpha,beta-unsaturated ketones

Alternative Parents

Substituents

Alpha-branched alpha,beta-unsaturated-ketone
Heteroaromatic compound
Furan
Enone
Acryloyl-group
Ketone
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: HMDB0035414)
Cytoplasm (HMDB: HMDB0035414)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035414)

Source

Exogenous

Exogenous (HMDB: HMDB0035414)

Food

Food (HMDB: HMDB0035414)

Herb and spice

Herb

Roman camomile (FooDB: FOOD00046)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0035414)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035414)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	249.00 to 250.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	457.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.945 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.68	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-3.1	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	4	ChemAxon
Refractivity	47.04 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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
DarkChem	[M+H]+	138.009	31661259
DarkChem	[M-H]-	135.777	31661259
DeepCCS	[M+H]+	137.172	30932474
DeepCCS	[M-H]-	134.276	30932474
DeepCCS	[M-2H]-	170.872	30932474
DeepCCS	[M+Na]+	146.41	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	138.0	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.	4.85 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4743 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1645.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	470.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	172.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	268.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	447.0 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	664.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	126.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1122.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	389.3 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	1231.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	473.9 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	18.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lepalone	CC(=C)C(=O)CCC1=COC=C1	1754.2	Standard polar	33892256
Lepalone	CC(=C)C(=O)CCC1=COC=C1	1243.7	Standard non polar	33892256
Lepalone	CC(=C)C(=O)CCC1=COC=C1	1242.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lepalone,1TMS,isomer #1	C=C(C)C(=CCC1=COC=C1)O[Si](C)(C)C	1437.6	Semi standard non polar	33892256
Lepalone,1TMS,isomer #1	C=C(C)C(=CCC1=COC=C1)O[Si](C)(C)C	1430.5	Standard non polar	33892256
Lepalone,1TBDMS,isomer #1	C=C(C)C(=CCC1=COC=C1)O[Si](C)(C)C(C)(C)C	1660.8	Semi standard non polar	33892256
Lepalone,1TBDMS,isomer #1	C=C(C)C(=CCC1=COC=C1)O[Si](C)(C)C(C)(C)C	1644.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lepalone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9200000000-e6ce0d5fe57797e7d1ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lepalone 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 - Lepalone 10V, Positive-QTOF	splash10-014i-0900000000-a0f67f973e64c4f5bf67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 20V, Positive-QTOF	splash10-00kb-6900000000-3e22c8deb4b3797efb64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 40V, Positive-QTOF	splash10-00ke-9300000000-7f95b9c2b21c55610c9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 10V, Negative-QTOF	splash10-03di-0900000000-7687a34fb0374aca195f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 20V, Negative-QTOF	splash10-03di-1900000000-808bc118e119b1e3d9fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 40V, Negative-QTOF	splash10-00lu-6900000000-f92d250bd6c21faef42f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 10V, Negative-QTOF	splash10-03di-0900000000-563e8a53be8cdd6dee19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 20V, Negative-QTOF	splash10-03xr-6900000000-0dbdf9e60b67666ea144	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 40V, Negative-QTOF	splash10-05po-9200000000-47a0cb83ccd03553d473	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 10V, Positive-QTOF	splash10-00ke-9100000000-d91c1b072d54e013e258	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 20V, Positive-QTOF	splash10-004l-9000000000-683928ed108a1ab4aeae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lepalone 40V, Positive-QTOF	splash10-014l-9000000000-d46cea8d48849cf2f231	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+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

FDB014091

KNApSAcK ID

C00010329

Chemspider ID

466192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

535169

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1119171

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 Lepalone (HMDB0035414)

MOL for HMDB0035414 (Lepalone)

3D MOL for HMDB0035414 (Lepalone)

3D SDF for HMDB0035414 (Lepalone)

3D-SDF for HMDB0035414 (Lepalone)

PDB for HMDB0035414 (Lepalone)

3D PDB for HMDB0035414 (Lepalone)

SMILES for HMDB0035414 (Lepalone)

INCHI for HMDB0035414 (Lepalone)

Structure for HMDB0035414 (Lepalone)

3D Structure for HMDB0035414 (Lepalone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra