Cannabis Compound Database: Showing Compound Card for trans-2-Heptenal (CDB000688)

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Record Information

Version

1.0

Created at

2020-03-19 00:51:17 UTC

Updated at

2020-12-07 19:07:41 UTC

CannabisDB ID

CDB000688

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

trans-2-Heptenal

Description

2-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-Heptenal	ChEBI
(e)-2-Hepten-1-al	ChEBI
2-trans-Heptenal	ChEBI
3-Butylacrolein	ChEBI
beta-Butylacrolein	ChEBI
Hept-(e)-2-enal	ChEBI
Hept-2(e)-enal	ChEBI
Hept-trans-2-enal	ChEBI
N-Hept-trans-2-enal	ChEBI
trans-2-Hepten-1-al	ChEBI
trans-2-Heptenal	ChEBI
b-Butylacrolein	Generator
Β-butylacrolein	Generator
(e)-2-Heptenal	ChEMBL, HMDB
2-Hept-enal	HMDB
alpha-Heptenal	HMDB
Butylacrolein	HMDB
FEMA 3165	HMDB
2-Heptenal, (e)-isomer	MeSH, HMDB
2-Heptenal	MeSH

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.17

Monoisotopic Molecular Weight

112.0888

IUPAC Name

(2E)-hept-2-enal

Traditional Name

2-heptenal, (2E)-

CAS Registry Number

2463-63-0

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 Key

NDFKTBCGKNOHPJ-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000019 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Indirect biological role:

Uremic toxin

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.3	ALOGPS
logP	2.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.84 m³·mol⁻¹	ChemAxon
Polarizability	13.59 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-78a71f46d13bfca3d317	2015-03-01	View Spectrum
GC-MS	trans-2-Heptenal , non-derivatized, GC-MS Spectrum	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	Spectrum
GC-MS	trans-2-Heptenal , non-derivatized, GC-MS Spectrum	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	Spectrum
Predicted GC-MS	trans-2-Heptenal , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ou-9000000000-5dedb721b6e6ec596371	Spectrum
Predicted GC-MS	trans-2-Heptenal , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-6900000000-4a2743833647b0bdb535	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-9400000000-6ff3124de5daea2c5dc7	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-9000000000-21a1a7ea291def5b6e29	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-316d71b866cb472295ff	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-4900000000-af5169f2777e09a2d955	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-144150625b2c04635793	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-914db82f697f24d29d0c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-ac71f7a8d0b92d89ca07	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0rkc-9000000000-de34104ae53e4248a8d1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-8d02e35f9ff6d556c0bb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066u-9000000000-aa11d319dd6879fab78a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0673-9000000000-46f63dfa7a32f461d5ac	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
NADPH oxidase 4	NOX4	11q14.2-q21	Q9NPH5	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
NADPH oxidase 4	NOX4	11q14.2-q21	Q9NPH5	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0033827

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008060

KNApSAcK ID

C00034755

Chemspider ID

4446437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283316

PDB ID

Not Available

ChEBI ID

143912

References

General References

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 ]
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 ]
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 ]
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

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

Structure for CDB000688 (trans-2-Heptenal )

Enzymes