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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:01 UTC

Update Date

2023-02-21 17:20:15 UTC

HMDB ID

HMDB0031271

Secondary Accession Numbers

HMDB31271

Metabolite Identification

Common Name

2-Nonenoic acid

Description

2-Nonenoic acid, also known as 2-nonenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on 2-Nonenoic acid.

Structure

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

COMPND    HMDB0031271
HETATM    1  C1  UNL     1      -2.910   1.200   0.186  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.169  -0.268   0.053  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.090  -1.163   0.529  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.776  -1.115  -0.139  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.063   0.180  -0.109  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.309   0.091  -0.800  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.176  -0.891  -0.149  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.328  -0.562   0.386  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.930   0.744   0.438  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.078   0.849   1.015  1.00  0.00           O  
HETATM   11  O2  UNL     1       3.418   1.912  -0.063  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.127   1.446   0.901  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.796   1.687  -0.816  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.841   1.713   0.615  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.138  -0.492   0.601  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.448  -0.499  -1.021  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.471  -2.236   0.441  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.980  -1.064   1.661  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.938  -1.455  -1.215  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.101  -1.920   0.274  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.115   0.630   0.862  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.618   0.893  -0.782  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.653   1.114  -0.881  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.122  -0.243  -1.880  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.884  -1.953  -0.091  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.897  -1.414   0.855  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.557   2.815   0.353  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Nonenoate	Generator
alpha-Nonenoic acid	HMDB
a-Nonylenate	Generator
a-Nonylenic acid	Generator
alpha-Nonylenate	Generator
Α-nonylenate	Generator
Α-nonylenic acid	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

(2Z)-non-2-enoic acid

Traditional Name

α-nonylenic acid

CAS Registry Number

3760-11-0

SMILES

CCCCCC\C=C/C(O)=O

InChI Identifier

InChI=1S/C9H16O2/c1-2-3-4-5-6-7-8-9(10)11/h7-8H,2-6H2,1H3,(H,10,11)/b8-7-

InChI Key

ADLXTJMPCFOTOO-FPLPWBNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Unsaturated fatty acids (LMFA01030026 )

Ontology

Physiological effect

Organoleptic effect

Odor

Fatty

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0031271)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031271)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031271)

Source

Endogenous

Endogenous (HMDB: HMDB0031271)

Plant

Plant (HMDB: HMDB0031271)

Animal

Animal (HMDB: HMDB0031271)

Exogenous

Food

Food (HMDB: HMDB0031271)

Vegetable

Mushroom

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031271)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031271)

Cellular process

Cell signaling (HMDB: HMDB0031271)

Biochemical process

Lipid transport (HMDB: HMDB0031271)

Role

Biological role

Energy storage (HMDB: HMDB0031271)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031271)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031271)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	173.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.205 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	3.53	ALOGPS
logP	3.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.97 m³·mol⁻¹	ChemAxon
Polarizability	18.26 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
DarkChem	[M+H]+	138.627	31661259
DarkChem	[M-H]-	136.786	31661259
DeepCCS	[M+H]+	140.533	30932474
DeepCCS	[M-H]-	137.27	30932474
DeepCCS	[M-2H]-	174.154	30932474
DeepCCS	[M+Na]+	149.34	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.4	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	140.1	32859911
AllCCS	[M+Na-2H]-	142.0	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Nonenoic acid	CCCCCC\C=C/C(O)=O	2389.3	Standard polar	33892256
2-Nonenoic acid	CCCCCC\C=C/C(O)=O	1289.1	Standard non polar	33892256
2-Nonenoic acid	CCCCCC\C=C/C(O)=O	1316.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Nonenoic acid,1TMS,isomer #1	CCCCCC/C=C\C(=O)O[Si](C)(C)C	1408.3	Semi standard non polar	33892256
2-Nonenoic acid,1TBDMS,isomer #1	CCCCCC/C=C\C(=O)O[Si](C)(C)C(C)(C)C	1627.2	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 - 2-Nonenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05vx-9200000000-db0470cd2590290f4327	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-b7e7fa893aa3c895a6b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenoic acid 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 - 2-Nonenoic acid 10V, Positive-QTOF	splash10-0a4r-1900000000-4daf532e8c589379a5df	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 20V, Positive-QTOF	splash10-06r2-9700000000-dbb058a0c542b5c51d05	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 40V, Positive-QTOF	splash10-052f-9000000000-b96f42f4e354e6f63431	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-e45a3c6d49dba9f3358d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 20V, Negative-QTOF	splash10-0bt9-1900000000-a4a82417dc5dc2319546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 40V, Negative-QTOF	splash10-06r6-9300000000-08033724f984032d13db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 10V, Positive-QTOF	splash10-0ap3-9200000000-fd07561fb682dc469678	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 20V, Positive-QTOF	splash10-066r-9000000000-4637f914abdcc4d785e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 40V, Positive-QTOF	splash10-05mo-9000000000-870a85af4fba9e1418a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 10V, Negative-QTOF	splash10-0a4r-0900000000-67901ff4637f95391a06	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 20V, Negative-QTOF	splash10-08fr-0900000000-1c6aa327175ad89a8588	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenoic acid 40V, Negative-QTOF	splash10-0006-9000000000-999803a32af745cba98b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB003314

KNApSAcK ID

C00016254

Chemspider ID

4445849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282722

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1047931

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 2-Nonenoic acid (HMDB0031271)

MOL for HMDB0031271 (2-Nonenoic acid)

3D MOL for HMDB0031271 (2-Nonenoic acid)

3D SDF for HMDB0031271 (2-Nonenoic acid)

3D-SDF for HMDB0031271 (2-Nonenoic acid)

PDB for HMDB0031271 (2-Nonenoic acid)

3D PDB for HMDB0031271 (2-Nonenoic acid)

SMILES for HMDB0031271 (2-Nonenoic acid)

INCHI for HMDB0031271 (2-Nonenoic acid)

Structure for HMDB0031271 (2-Nonenoic acid)

3D Structure for HMDB0031271 (2-Nonenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra