Showing Compound Card for trans-2-Heptenal (CDB000688)

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Record Information
Version1.0
Created at2020-03-19 00:51:17 UTC
Updated at2020-12-07 19:07:41 UTC
CannabisDB IDCDB000688
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-2-Heptenal
Description2-heptenal known as trans-2-heptenal or 3-butylacrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, 2-heptenal is considered to be a fatty aldehyde. 2-heptenal is a very hydrophobic, neutral molecule, it exists as a clear, colorless liquid and is practically insoluble in water. 2-heptenal occurs in two isomeric forms (trans - and cis -2-heptenal), with the trans form being of greater importance. 2-heptenal is found in the peel of Malaysian pink and white pomelo peel. The trans-form of 2-heptenal is also found in the scent gland secretion of the rice stink bug Oebalus pugnax (PMID: 17739573 ). 2-heptenal has been found in pulses (such as peas and other legumes) and has been isolated from soya bean oil (Glycine max) as well as safflower oil. 2-heptenal has also been detected, but not quantified in, several different fruits, grains and other foods, such as common grapes, oats, roselles, and watermelons. 2-heptenal has also been reported to be found in Cannabis sativa (PMID: 6991645 , 26657499 ). 2-heptenal has a green, fatty, fruit odor and a green, sweet, fresh or apple like flavor. 2-heptenal is also a known uremic toxin (PMID: 22626821 ). 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 in individuals suffering from uremia. Uremia or uremic syndrome can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight112.17
Monoisotopic Molecular Weight112.0888
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

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-78a71f46d13bfca3d3172015-03-01View Spectrum
GC-MStrans-2-Heptenal , non-derivatized, GC-MS Spectrumsplash10-0a6u-9000000000-1e3da23b690c3ef7c024Spectrum
GC-MStrans-2-Heptenal , non-derivatized, GC-MS Spectrumsplash10-0a6u-9000000000-1e3da23b690c3ef7c024Spectrum
Predicted GC-MStrans-2-Heptenal , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ou-9000000000-5dedb721b6e6ec596371Spectrum
Predicted GC-MStrans-2-Heptenal , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-6900000000-4a2743833647b0bdb5352016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9400000000-6ff3124de5daea2c5dc72016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9000000000-21a1a7ea291def5b6e292016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-316d71b866cb472295ff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-af5169f2777e09a2d9552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-144150625b2c046357932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-914db82f697f24d29d0c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-ac71f7a8d0b92d89ca072021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0rkc-9000000000-de34104ae53e4248a8d12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-8d02e35f9ff6d556c0bb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-9000000000-aa11d319dd6879fab78a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-9000000000-46f63dfa7a32f461d5ac2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
NADPH oxidase 4NOX411q14.2-q21Q9NPH5 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
NADPH oxidase 4NOX411q14.2-q21Q9NPH5 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033827
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Blum MS, Traynham JG, Chidester JB, Boggus JD: n-Tridecane and trans-2-Heptenal in Scent Gland of the Rice Stink Bug Oebalus pugnax (F.). Science. 1960 Nov 18;132(3438):1480-1. doi: 10.1126/science.132.3438.1480. [PubMed:17739573 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  4. 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 ]

Enzymes

Enzyme Details
1. NADPH oxidase 4
General function:
Involved in oxidoreductase activity
Specific function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 4 displays an increased activity. Isoform 5 and isoform 6 display reduced activity
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular weight:
66931.0