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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:06 UTC
Update Date2020-10-09 21:09:34 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. 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 a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (2E)-2-Heptenal is an almond, fat, and fatty tasting compound. Outside of the human body, (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. This could make (2E)-2-heptenal a potential biomarker for the consumption of these foods (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-HeptenalHMDB
2-Hept-enalHMDB
alpha-HeptenalHMDB
ButylacroleinHMDB
FEMA 3165HMDB
2-Heptenal, (e)-isomerHMDB
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6u-9000000000-1e3da23b690c3ef7c024Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6u-9000000000-1e3da23b690c3ef7c024Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9000000000-5dedb721b6e6ec596371Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-316d71b866cb472295ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-af5169f2777e09a2d955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-144150625b2c04635793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-6900000000-4a2743833647b0bdb535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9400000000-6ff3124de5daea2c5dc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9000000000-21a1a7ea291def5b6e29Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-78a71f46d13bfca3d317Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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
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.. .