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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:58 UTC

Update Date

2023-02-21 17:21:23 UTC

HMDB ID

HMDB0031854

Secondary Accession Numbers

HMDB31854

Metabolite Identification

Common Name

3-Methyl-5-propyl-2-cyclohexen-1-one

Description

3-Methyl-5-propyl-2-cyclohexen-1-one, also known as celery ketone or fema 3577, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on 3-Methyl-5-propyl-2-cyclohexen-1-one.

Structure

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

COMPND    HMDB0031854
HETATM    1  C1  UNL     1       3.044  -0.405   0.706  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.692   0.627  -0.347  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.447   0.212  -1.087  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.305   0.068  -0.148  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.024   1.376   0.542  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.024   1.067   1.564  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.894   1.378   2.774  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.211   0.385   1.092  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.175  -0.268  -0.050  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.403  -0.990  -0.568  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.974  -0.340  -0.885  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.148  -0.426   0.844  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.698  -1.393   0.345  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.587  -0.171   1.687  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.646   1.614   0.128  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.557   0.723  -1.080  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.157   1.033  -1.810  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.619  -0.740  -1.658  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.510  -0.670   0.674  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.875   1.896   0.957  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.496   2.022  -0.218  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.136   0.401   1.664  1.00  0.00           H  
HETATM   23  H12 UNL     1      -4.274  -0.761   0.061  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.603  -0.630  -1.609  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.205  -2.073  -0.539  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.045   0.241  -1.823  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.870  -1.413  -1.216  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   11   19
CONECT    5    6   20   21
CONECT    6    7    7    8
CONECT    8    9    9   22
CONECT    9   10   11
CONECT   10   23   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methyl-5-propylcyclohex-2-enone	HMDB
Celery ketone	HMDB
FEMA 3577	HMDB
(S)-Celery ketone	MeSH
3-Methyl-5-propylcyclohex-2-en-1-one	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

3-methyl-5-propylcyclohex-2-en-1-one

Traditional Name

3-methyl-5-propylcyclohex-2-en-1-one

CAS Registry Number

3720-16-9

SMILES

CCCC1CC(C)=CC(=O)C1

InChI Identifier

InChI=1S/C10H16O/c1-3-4-9-5-8(2)6-10(11)7-9/h6,9H,3-5,7H2,1-2H3

InChI Key

URQMEZRQHLCJKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0031854)
Cell membrane (HMDB: HMDB0031854)

Source

Endogenous

Endogenous (HMDB: HMDB0031854)

Exogenous

Food

Food (HMDB: HMDB0031854)

Exogenous (HMDB: HMDB0031854)

Process

Not Available

Role

Not Available

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	0.72 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.91	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	19.5	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.37 m³·mol⁻¹	ChemAxon
Polarizability	18.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	133.815	31661259
DarkChem	[M-H]-	132.214	31661259
DeepCCS	[M+H]+	139.656	30932474
DeepCCS	[M-H]-	135.948	30932474
DeepCCS	[M-2H]-	173.542	30932474
DeepCCS	[M+Na]+	148.868	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.8	32859911
AllCCS	[M-H]-	138.2	32859911
AllCCS	[M+Na-2H]-	139.7	32859911
AllCCS	[M+HCOO]-	141.5	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.	6.32 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6684 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2098.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	534.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	332.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	605.5 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	675.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1302.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	433.7 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	1300.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	452.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	492.8 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	18.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-propyl-2-cyclohexen-1-one	CCCC1CC(C)=CC(=O)C1	1849.0	Standard polar	33892256
3-Methyl-5-propyl-2-cyclohexen-1-one	CCCC1CC(C)=CC(=O)C1	1273.3	Standard non polar	33892256
3-Methyl-5-propyl-2-cyclohexen-1-one	CCCC1CC(C)=CC(=O)C1	1270.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-propyl-2-cyclohexen-1-one,1TMS,isomer #1	CCCC1C=C(O[Si](C)(C)C)C=C(C)C1	1400.8	Semi standard non polar	33892256
3-Methyl-5-propyl-2-cyclohexen-1-one,1TMS,isomer #1	CCCC1C=C(O[Si](C)(C)C)C=C(C)C1	1375.5	Standard non polar	33892256
3-Methyl-5-propyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CCCC1C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C1	1620.3	Semi standard non polar	33892256
3-Methyl-5-propyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CCCC1C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C1	1595.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-055f-9300000000-d6432f4d6c19b1beeb54	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 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 - 3-Methyl-5-propyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-0udi-0900000000-da43c939e0c11feb26ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-0zfr-8900000000-5d1a10ba524e1554c679	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-0gbc-9100000000-f67488945534309e35b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-0udi-0900000000-51a5b6f08faf69e132be	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-0udi-0900000000-b4ba3d32f072569e4881	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-0pcc-6900000000-8136785990b1f7b1ff87	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-0udi-2900000000-952ce188d1a895492ceb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-066u-9500000000-63b7fc1a1fa18cb2b582	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-00kf-9100000000-3a53b41b22952a57b106	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-0udi-0900000000-ac9fa430b77cee767c1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-propyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-00di-0900000000-eb7b4d0dca5ecbaeaef3	2021-09-22	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

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

FDB008538

KNApSAcK ID

Not Available

Chemspider ID

3010274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3782139

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 3-Methyl-5-propyl-2-cyclohexen-1-one (HMDB0031854)

MOL for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

3D MOL for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

3D SDF for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

3D-SDF for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

PDB for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

3D PDB for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

SMILES for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

INCHI for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

Structure for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

3D Structure for HMDB0031854 (3-Methyl-5-propyl-2-cyclohexen-1-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra