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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:06 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033827
Secondary Accession Numbers
  • HMDB33827
Metabolite Identification
Common Name(2E)-2-Heptenal
Description(2E)-2-Heptenal, also known as 3-butylacrolein or 2-trans-heptenal, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. (2E)-2-Heptenal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (2E)-2-heptenal is considered to be a fatty aldehyde lipid molecule. Uremic toxins such as 2-Heptenal are actively transported into the kidneys via organic ion transporters (especially OAT3). (2E)-2-Heptenal is an almond, and fatty tasting compound. (2E)-2-Heptenal is found, on average, in the highest concentration within safflowers. (2E)-2-Heptenal has also been detected, but not quantified, in several different foods, such as roselles, common grapes, cucumbers, garden tomato, and evergreen blackberries. (2E)-2-Heptenal is a potentially toxic compound. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. As a uremic toxin, this compound can cause uremic syndrome. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
Structure
Data?1563862467
Synonyms
ValueSource
(2E)-HeptenalChEBI
(e)-2-Hepten-1-alChEBI
2-trans-HeptenalChEBI
3-ButylacroleinChEBI
beta-ButylacroleinChEBI
Hept-(e)-2-enalChEBI
Hept-2(e)-enalChEBI
Hept-trans-2-enalChEBI
N-Hept-trans-2-enalChEBI
trans-2-Hepten-1-alChEBI
trans-2-HeptenalChEBI
b-ButylacroleinGenerator
Β-butylacroleinGenerator
(e)-2-HeptenalChEMBL, HMDB
2-Hept-enalHMDB
alpha-HeptenalHMDB
ButylacroleinHMDB
FEMA 3165HMDB
2-Heptenal, (e)-isomerMeSH, HMDB
2-HeptenalMeSH
Chemical FormulaC7H12O
Average Molecular Weight112.1696
Monoisotopic Molecular Weight112.088815006
IUPAC Name(2E)-hept-2-enal
Traditional Name2-heptenal, (2E)-
CAS Registry Number2463-63-0
SMILES
CCCC\C=C\C=O
InChI Identifier
InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+
InChI KeyNDFKTBCGKNOHPJ-AATRIKPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point90.00 to 91.00 °C. @ 50.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.300 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP2.3ALOGPS
logP2.09ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.84 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.81631661259
DarkChem[M-H]-122.4631661259
DeepCCS[M+H]+130.88430932474
DeepCCS[M-H]-128.98930932474
DeepCCS[M-2H]-164.66830932474
DeepCCS[M+Na]+139.18930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2E)-2-HeptenalCCCC\C=C\C=O1279.3Standard polar33892256
(2E)-2-HeptenalCCCC\C=C\C=O921.0Standard non polar33892256
(2E)-2-HeptenalCCCC\C=C\C=O948.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (2E)-2-Heptenal EI-B (Non-derivatized)splash10-0a6u-9000000000-1e3da23b690c3ef7c0242017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (2E)-2-Heptenal EI-B (Non-derivatized)splash10-0a6u-9000000000-1e3da23b690c3ef7c0242018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2E)-2-Heptenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9000000000-5dedb721b6e6ec5963712016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2E)-2-Heptenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-78a71f46d13bfca3d3172015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Positive-QTOFsplash10-03di-6900000000-4a2743833647b0bdb5352016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Positive-QTOFsplash10-03dj-9400000000-6ff3124de5daea2c5dc72016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Positive-QTOFsplash10-0k96-9000000000-21a1a7ea291def5b6e292016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Negative-QTOFsplash10-03di-1900000000-316d71b866cb472295ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Negative-QTOFsplash10-03di-4900000000-af5169f2777e09a2d9552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Negative-QTOFsplash10-0006-9000000000-144150625b2c046357932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Negative-QTOFsplash10-03di-3900000000-914db82f697f24d29d0c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Negative-QTOFsplash10-0006-9200000000-ac71f7a8d0b92d89ca072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Negative-QTOFsplash10-0rkc-9000000000-de34104ae53e4248a8d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Positive-QTOFsplash10-0a4i-9000000000-8d02e35f9ff6d556c0bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Positive-QTOFsplash10-066u-9000000000-aa11d319dd6879fab78a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Positive-QTOFsplash10-0673-9000000000-46f63dfa7a32f461d5ac2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.16 +/- 0.05 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.49 +/- 0.15 uMAdult (>18 years old)Bothuremia details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008060
KNApSAcK IDC00034755
Chemspider ID4446437
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283316
PDB IDNot Available
ChEBI ID143912
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029828
Good Scents IDrw1028241
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .