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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:57:52 UTC

Update Date

2023-02-21 17:24:58 UTC

HMDB ID

HMDB0035916

Secondary Accession Numbers

HMDB35916

Metabolite Identification

Common Name

(E)-2-Nonen-4-one

Description

(E)-2-Nonen-4-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR' (E)-2-Nonen-4-one is a fruity tasting compound (E)-2-Nonen-4-one has been detected, but not quantified in, a few different foods, such as alcoholic beverages, herbs and spices, and potatos (Solanum tuberosum). This could make (e)-2-nonen-4-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-2-Nonen-4-one.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₆O

Average Molecular Weight

140.2227

Monoisotopic Molecular Weight

140.120115134

IUPAC Name

(2Z)-non-2-en-4-one

Traditional Name

(2Z)-non-2-en-4-one

CAS Registry Number

27743-70-0

SMILES

CCCCCC(=O)\C=C/C

InChI Identifier

InChI=1S/C9H16O/c1-3-5-6-8-9(10)7-4-2/h4,7H,3,5-6,8H2,1-2H3/b7-4-

InChI Key

WTAYWTBOEQYGOG-DAXSKMNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Fruity

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035916)
Cell membrane (HMDB: HMDB0035916)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035916)

Source

Exogenous

Exogenous (HMDB: HMDB0035916)

Food

Food (HMDB: HMDB0035916)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0035916)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035916)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	200.00 to 201.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.689 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.28	ChemAxon
logS	-2.4	ALOGPS
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	5	ChemAxon
Refractivity	44.95 m³·mol⁻¹	ChemAxon
Polarizability	17.23 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	138.761	30932474
DeepCCS	[M-H]-	136.161	30932474
DeepCCS	[M-2H]-	173.146	30932474
DeepCCS	[M+Na]+	148.143	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.5	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	138.2	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	143.1	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.	6.72 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2521 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2030.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	498.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	324.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	605.8 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	629.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1351.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	438.4 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	1291.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	469.5 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	9.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Nonen-4-one	CCCCCC(=O)\C=C/C	1435.0	Standard polar	33892256
(E)-2-Nonen-4-one	CCCCCC(=O)\C=C/C	1089.5	Standard non polar	33892256
(E)-2-Nonen-4-one	CCCCCC(=O)\C=C/C	1107.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Nonen-4-one,1TMS,isomer #1	C/C=C\C(=CCCCC)O[Si](C)(C)C	1323.7	Semi standard non polar	33892256
(E)-2-Nonen-4-one,1TMS,isomer #1	C/C=C\C(=CCCCC)O[Si](C)(C)C	1294.3	Standard non polar	33892256
(E)-2-Nonen-4-one,1TBDMS,isomer #1	C/C=C\C(=CCCCC)O[Si](C)(C)C(C)(C)C	1560.2	Semi standard non polar	33892256
(E)-2-Nonen-4-one,1TBDMS,isomer #1	C/C=C\C(=CCCCC)O[Si](C)(C)C(C)(C)C	1488.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Nonen-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9100000000-3c0c479f8ed00504ce67	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Nonen-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Nonen-4-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 - (E)-2-Nonen-4-one 10V, Positive-QTOF	splash10-0006-0900000000-31d5298185c0c9fae76c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 20V, Positive-QTOF	splash10-0596-9400000000-3c325cdc501fe5d8b879	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 40V, Positive-QTOF	splash10-052f-9000000000-45f13b4c211def58e02c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 10V, Negative-QTOF	splash10-000i-0900000000-412e469f4c5aa6f7316b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 20V, Negative-QTOF	splash10-000i-5900000000-f8acd0d698e3967f1fa4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 40V, Negative-QTOF	splash10-001l-9100000000-0133995217fadc880ab7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 10V, Negative-QTOF	splash10-000i-0900000000-343e1c1d3f36a1c8322d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 20V, Negative-QTOF	splash10-000j-9600000000-b76e4a6f6796e1f9eaaa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 40V, Negative-QTOF	splash10-014i-9000000000-c216a251cb4c5ffc1e3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 10V, Positive-QTOF	splash10-0006-9100000000-ee9af622dacceb4bcb6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 20V, Positive-QTOF	splash10-01bc-9000000000-50718bf5b239d4a9eac9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Nonen-4-one 40V, Positive-QTOF	splash10-00kf-9000000000-51fcb757e0847f54fac2	2021-09-24	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

FDB014709

KNApSAcK ID

Not Available

Chemspider ID

30777148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12409826

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1558981

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 (E)-2-Nonen-4-one (HMDB0035916)

MOL for HMDB0035916 ((E)-2-Nonen-4-one)

3D MOL for HMDB0035916 ((E)-2-Nonen-4-one)

3D SDF for HMDB0035916 ((E)-2-Nonen-4-one)

3D-SDF for HMDB0035916 ((E)-2-Nonen-4-one)

PDB for HMDB0035916 ((E)-2-Nonen-4-one)

3D PDB for HMDB0035916 ((E)-2-Nonen-4-one)

SMILES for HMDB0035916 ((E)-2-Nonen-4-one)

INCHI for HMDB0035916 ((E)-2-Nonen-4-one)

Structure for HMDB0035916 ((E)-2-Nonen-4-one)

3D Structure for HMDB0035916 ((E)-2-Nonen-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra