Jump To Section:

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 17:43:36 UTC

Update Date

2023-02-21 17:20:38 UTC

HMDB ID

HMDB0031484

Secondary Accession Numbers

HMDB31484

Metabolite Identification

Common Name

2-Heptenoic acid

Description

2-Heptenoic acid, also known as 7:1, N-5 trans or (e)-2-heptenoate, 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 small amount of articles have been published on 2-Heptenoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e)-2-Heptenoic acid	ChEBI
7:1, N-5 trans	ChEBI
C7:1, N-5 trans	ChEBI
Hept-2t-enoic acid	ChEBI
Hept-2t-ensaeure	ChEBI
trans-2-Heptenoic acid	ChEBI
trans-acide heptene-2-oique	ChEBI
trans-Hept-2-enoic acid	ChEBI
trans-Hept-2-ensaeure	ChEBI
(e)-2-Heptenoate	Generator
Hept-2t-enoate	Generator
trans-2-Heptenoate	Generator
trans-Hept-2-enoate	Generator
2-Heptenoate	Generator
(e)-Hept-2-enoic acid	ChEBI, HMDB
(e)-Hept-2-enoate	Generator, HMDB
2-Heptenic acid	HMDB
Hept-2-enoic acid	HMDB
Hex-1-ene-1-carboxylic acid	HMDB
a-Heptenoate	Generator
a-Heptenoic acid	Generator
alpha-Heptenoate	Generator
Α-heptenoate	Generator
Α-heptenoic acid	Generator

Chemical Formula

C₇H₁₂O₂

Average Molecular Weight

128.169

Monoisotopic Molecular Weight

128.083729628

IUPAC Name

(2E)-hept-2-enoic acid

Traditional Name

(E)-2-heptenoic acid

CAS Registry Number

18999-28-5

SMILES

CCCC\C=C\C(O)=O

InChI Identifier

InChI=1S/C7H12O2/c1-2-3-4-5-6-7(8)9/h5-6H,2-4H2,1H3,(H,8,9)/b6-5+

InChI Key

YURNCBVQZBJDAJ-AATRIKPKSA-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

2-heptenoic acid (CHEBI:38364 )
Unsaturated fatty acids (LMFA01030012 )

Ontology

Physiological effect

Organoleptic effect

Odor

Rancid

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB31484)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB31484)

Route of exposure

Enteral

Ingestion (HMDB: HMDB31484)

Source

Endogenous

Endogenous (HMDB: HMDB31484)

Animal

Animal (HMDB: HMDB31484)

Exogenous

Food

Food (HMDB: HMDB31484)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB31484)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB31484)

Lipid metabolism pathway (HMDB: HMDB31484)

Cellular process

Cell signaling (HMDB: HMDB31484)

Biochemical process

Lipid transport (HMDB: HMDB31484)

Role

Biological role

Energy source (HMDB: HMDB31484)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB31484)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB31484)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	224.00 to 228.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2389 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.186 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.25	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	5.2	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	4	ChemAxon
Refractivity	36.77 m³·mol⁻¹	ChemAxon
Polarizability	14.36 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]+	131.928	31661259
DarkChem	[M-H]-	127.633	31661259
DeepCCS	[M+H]+	134.475	30932474
DeepCCS	[M-H]-	131.696	30932474
DeepCCS	[M-2H]-	168.226	30932474
DeepCCS	[M+Na]+	143.117	30932474
AllCCS	[M+H]+	130.9	32859911
AllCCS	[M+H-H2O]+	126.7	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.0	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	137.4	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.	4.51 minutes	32390414
Predicted by Siyang on May 30, 2022	14.238 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1888.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	447.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	165.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	321.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	294.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	560.5 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	558.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	181.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	417.2 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	1287.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	527.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	446.7 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	41.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Heptenoic acid	CCCC\C=C\C(O)=O	2090.6	Standard polar	33892256
2-Heptenoic acid	CCCC\C=C\C(O)=O	1110.5	Standard non polar	33892256
2-Heptenoic acid	CCCC\C=C\C(O)=O	1121.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Heptenoic acid,1TMS,isomer #1	CCCC/C=C/C(=O)O[Si](C)(C)C	1220.5	Semi standard non polar	33892256
2-Heptenoic acid,1TBDMS,isomer #1	CCCC/C=C/C(=O)O[Si](C)(C)C(C)(C)C	1441.7	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-Heptenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-bf076a570fda949c9d7c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Heptenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00g3-9300000000-061f7c4ac9e7d7935c99	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Heptenoic 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-Heptenoic acid 10V, Positive-QTOF	splash10-01t9-3900000000-2444977204cf89f66c01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 20V, Positive-QTOF	splash10-0159-9200000000-7c291d5de5205546035f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 40V, Positive-QTOF	splash10-00kf-9000000000-8eb35284fa6c2ae3e9fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 10V, Negative-QTOF	splash10-004i-1900000000-024156a01be0710ecfd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 20V, Negative-QTOF	splash10-0059-6900000000-55b550176613ad972ddf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 40V, Negative-QTOF	splash10-0536-9100000000-47b2d7eb5638893040ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-aa39684fdf4e1f7af309	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 20V, Negative-QTOF	splash10-052f-9600000000-634f99268823b7c2e906	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 40V, Negative-QTOF	splash10-014l-9000000000-65df628afae35b2b671f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 10V, Positive-QTOF	splash10-0a4l-9200000000-897e7dd738f8e0a75f34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 20V, Positive-QTOF	splash10-0aou-9000000000-d539f4ee3804620624d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Heptenoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-d7abb3c5cccad8e86b68	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm
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

FDB014141

KNApSAcK ID

C00011896

Chemspider ID

4445836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282709

PDB ID

Not Available

ChEBI ID

38364

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1436261

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-Heptenoic acid (HMDB0031484)

MOL for HMDB0031484 (2-Heptenoic acid)

3D MOL for HMDB0031484 (2-Heptenoic acid)

3D SDF for HMDB0031484 (2-Heptenoic acid)

3D-SDF for HMDB0031484 (2-Heptenoic acid)

PDB for HMDB0031484 (2-Heptenoic acid)

3D PDB for HMDB0031484 (2-Heptenoic acid)

SMILES for HMDB0031484 (2-Heptenoic acid)

INCHI for HMDB0031484 (2-Heptenoic acid)

Structure for HMDB0031484 (2-Heptenoic acid)

3D Structure for HMDB0031484 (2-Heptenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra