Showing Compound Card for Heptanal (CDB000072)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:44 UTC
Updated at2020-12-07 19:07:03 UTC
CannabisDB IDCDB000072
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHeptanal
DescriptionHeptanal, also known as enanthal or N-heptaldehyde, 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, heptanal is a fatty aldehyde lipid molecule. It is an endogenous aldehyde resulting from membrane lipid oxidation. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor with an aldehydic, citrus, and fat taste. It is miscible with alcohols and practically insoluble in water. Heptanal is very hydrophobic and is relatively neutral. Heptanal exists in all eukaryotes, from yeast to humans. It is found in highest concentrations in corns, tea, and sweet oranges and in a lower concentrations in lemons, wild carrots, and carrots. Heptanal was detected in horned melons, common beets, dills, red bell peppers, and malus (crab apple) making it a potential biomarker for the consumption of these foods. Heptanal was distilled from castor oil and first described in 1878 ( Ref:DOI ). Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus) ( Ref:DOI ).  Heptanal is a simple aldehyde found in cannabis plants (PMID: 6991645 ). Because of heptanal’s strong fruity odor, it is used as precursor to components in perfumes and lubricants ( Ref:DOI ). For example, heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to alpha-pentylcinnamaldehyde, which is also called jasmine aldehyde (because of the typical jasmine odor). This jasmine aldehyde has been used in fragrances. Heptanal may be a potential biomarker of lung cancer as it was found in the blood of lung cancer patients (PMID:28366212 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Aldehyde C-7ChEBI
EnanthalChEBI
EnanthaldehydeChEBI
Enanthic aldehydeChEBI
HeptaldehydeChEBI
HeptanaldehydeChEBI
Heptyl aldehydeChEBI
HeptylaldehydeChEBI
N-C6H13CHOChEBI
N-HeptaldehydeChEBI
N-HeptanalChEBI
N-HeptylaldehydeChEBI
OenanthalChEBI
OenanthaldehydeChEBI
Oenanthic aldehydeChEBI
OenantholChEBI
1-HeptaldehydeHMDB
1-HeptanalHMDB
Aldehyde C7HMDB
EnantholeHMDB
FEMA 2540HMDB
Heptan-1-alHMDB
OenantholeHMDB
HeptanalMeSH
Chemical FormulaC7H14O
Average Molecular Weight114.19
Monoisotopic Molecular Weight114.1045
IUPAC Nameheptanal
Traditional Nameheptanal
CAS Registry Number111-71-7
SMILES
CCCCCCC=O
InChI Identifier
InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3
InChI KeyFXHGMKSSBGDXIY-UHFFFAOYSA-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
  • Alpha-hydrogen 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-43.3 °CNot Available
Boiling Point152.8 °CWikipedia
Water Solubility1.25 mg/mL at 25 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.59ALOGPS
logP2.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.75 m³·mol⁻¹ChemAxon
Polarizability14.4 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)splash10-0006-9000000000-781fd8622d3cd4023d6f2014-09-20View Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
Predicted GC-MSHeptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056u-9000000000-721c1006ed41ad91802fSpectrum
Predicted GC-MSHeptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-66f451ed07dec07dc2bd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9300000000-f683fbeaae9661c3375f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-62e7748838e417c074ba2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-242e518285d8711c88d32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-2b9ed46fa89f52e6874e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-614ce9045eac88449a8a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-9000000000-e5c26cac568c7e70be7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-0497fb39284b3eae18e72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7f7db6b93b3268b348982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-87ba7764343ecec4c93f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-baad9901fa250e031cb52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-8ffddb005d2cb639ad092021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 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
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031475
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008048
KNApSAcK IDC00034880
Chemspider ID7838
KEGG Compound IDC14390
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeptanal
METLIN IDNot Available
PubChem Compound8130
PDB IDNot Available
ChEBI ID34787
References
General References
  1. 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 ]
  2. Oenning AL, Mores L, Dias AN, Carasek E: A new configuration for bar adsorptive microextraction (BAmuE) for the quantification of biomarkers (hexanal and heptanal) in human urine by HPLC providing an alternative for early lung cancer diagnosis. Anal Chim Acta. 2017 May 1;965:54-62. doi: 10.1016/j.aca.2017.02.034. Epub 2017 Mar 6. [PubMed:28366212 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0