FRCD

Common Name	2-Octenal(F05270)
2D Structure
Description	2-Octenal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. 2-Octenal is a flavouring ingredient. 2-Octenal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms.
FRCD ID	F05270
CAS Number	2363-89-5
PubChem CID	6427080
Formula	C8H14O
IUPAC Name	(Z)-oct-2-enal
InChI Key	LVBXEMGDVWVTGY-SREVYHEPSA-N
InChI	InChI=1S/C8H14O/c1-2-3-4-5-6-7-8-9/h6-8H,2-5H2,1H3/b7-6-
Canonical SMILES	CCCCCC=CC=O
Isomeric SMILES	CCCCC/C=C\C=O
Synonyms	UNII-4KO8L0782M (z)-2-octenal (Z)-Oct-2-enal 2-Octenal, (Z)- 4KO8L0782M 2-OCTENAL 20664-46-4 cis-2-Octenal EINECS 243-954-5 2-(Z)-Octenal
Classifies	Predicted: Veterinary Drug
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Organic oxygen compounds
Class	Organooxygen compounds
Subclass	Carbonyl compounds
Intermediate Tree Nodes	Aldehydes
Direct Parent	Medium-chain aldehydes
Alternative Parents	Hydrocarbon derivatives Organic oxides Enals
Molecular Framework	Aliphatic acyclic compounds
Substituents	Medium-chain aldehyde - Enal - Alpha,beta-unsaturated aldehyde - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
Description	This compound 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.

Property Name	Property Value
Molecular Weight	126.199
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	5
Complexity	84.6
Monoisotopic Mass	126.104
Exact Mass	126.104
XLogP	2.6
Formal Charge	0
Heavy Atom Count	9
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9877
Human Intestinal Absorption	HIA+	1.0000
Caco-2 Permeability	Caco2+	0.8604
P-glycoprotein Substrate	Non-substrate	0.6153
P-glycoprotein Inhibitor	Non-inhibitor	0.8752
P-glycoprotein Inhibitor	Non-inhibitor	0.7739
Renal Organic Cation Transporter	Non-inhibitor	0.8976
Distribution
Subcellular localization	Plasma membrane	0.4699
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7741
CYP450 2D6 Substrate	Non-substrate	0.8592
CYP450 3A4 Substrate	Non-substrate	0.7261
CYP450 1A2 Inhibitor	Inhibitor	0.7147
CYP450 2C9 Inhibitor	Non-inhibitor	0.9288
CYP450 2D6 Inhibitor	Non-inhibitor	0.9612
CYP450 2C19 Inhibitor	Non-inhibitor	0.9386
CYP450 3A4 Inhibitor	Non-inhibitor	0.9909
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.7350
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.8488
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9070
AMES Toxicity	Non AMES toxic	0.9132
Carcinogens	Carcinogens	0.5910
Fish Toxicity	High FHMT	0.9437
Tetrahymena Pyriformis Toxicity	High TPT	0.9991
Honey Bee Toxicity	High HBT	0.7510
Biodegradation	Ready biodegradable	0.6314
Acute Oral Toxicity	III	0.7461
Carcinogenicity (Three-class)	Non-required	0.5964

Model	Value	Unit
Absorption
Aqueous solubility	-1.9098	LogS
Caco-2 Permeability	1.5545	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.6469	LD50, mol/kg
Fish Toxicity	0.1736	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.3230	pIGC50, ug/L

Title	Journal	Date	Pubmed ID
Volatile molecular markers of VOO Thermo-oxidation: Effect of heating processes, macronutrients composition, and olive ripeness on the new emitted aldehydic compounds.	Food Res Int	2018 Apr	29579972
Effects of aliphatic aldehydes on the growth and patulin production of Penicillium expansum in apple juice.	Biosci Biotechnol Biochem	2013	23291770
Effect of soybean volatile compounds on Aspergillus flavus growth and aflatoxin production.	J Food Sci	2009 Mar	19323756
Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: a review.	Crit Rev Food Sci Nutr	2008 Feb	18274968

Targets

General Function:: Vitamin d binding
Specific Function:: May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
Gene Name:: KL
Uniprot ID:: Q9UEF7
Molecular Weight:: 116179.815 Da

Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]

General Function:: Superoxide-generating nadph oxidase 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 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
Gene Name:: NOX4
Uniprot ID:: Q9NPH5
Molecular Weight:: 66930.995 Da

Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:: SLC22A8
Uniprot ID:: Q8TCC7
Molecular Weight:: 59855.585 Da

Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]