ETHYLENE GLYCOL MONOPHENYL ETHER

General Information

Mainterm	ETHYLENE GLYCOL MONOPHENYL ETHER
Doc Type	EAF
CAS Reg.No.(or other ID)	122-99-6
Regnum

From www.fda.gov

2D Structure
CID	31236
IUPAC Name	2-phenoxyethanol
InChI	InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChI Key	QCDWFXQBSFUVSP-UHFFFAOYSA-N
Canonical SMILES	C1=CC=C(C=C1)OCCO
Molecular Formula	C8H10O2
Wikipedia	phenoxyethanol

From Pubchem

Property Name	Property Value
Molecular Weight	138.166
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Complexity	77.3
CACTVS Substructure Key Fingerprint	A A A D c c B w M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A C A S g k A I w B o A A B g C A A C B C A A A C C A A g I A A I i A A G C I g N N i K E M R q C O C C k w B E L q A e A Q A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	29.5
Monoisotopic Mass	138.068
Exact Mass	138.068
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	10
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.8292
Human Intestinal Absorption	HIA+	0.9834
Caco-2 Permeability	Caco2+	0.7609
P-glycoprotein Substrate	Non-substrate	0.7000
P-glycoprotein Inhibitor	Non-inhibitor	0.6856
P-glycoprotein Inhibitor	Non-inhibitor	0.6176
Renal Organic Cation Transporter	Non-inhibitor	0.7555
Distribution
Subcellular localization	Mitochondria	0.8297
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8203
CYP450 2D6 Substrate	Non-substrate	0.8053
CYP450 3A4 Substrate	Non-substrate	0.7146
CYP450 1A2 Inhibitor	Non-inhibitor	0.7318
CYP450 2C9 Inhibitor	Non-inhibitor	0.9482
CYP450 2D6 Inhibitor	Non-inhibitor	0.9613
CYP450 2C19 Inhibitor	Non-inhibitor	0.7656
CYP450 3A4 Inhibitor	Non-inhibitor	0.9650
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.8578
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.7361
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8449
AMES Toxicity	Non AMES toxic	0.9133
Carcinogens	Non-carcinogens	0.8174
Fish Toxicity	Low FHMT	0.8235
Tetrahymena Pyriformis Toxicity	Low TPT	0.7141
Honey Bee Toxicity	High HBT	0.7444
Biodegradation	Ready biodegradable	0.8235
Acute Oral Toxicity	III	0.8740
Carcinogenicity (Three-class)	Non-required	0.5595

From admetSAR

Model	Value	Unit
Absorption
Aqueous solubility	-0.7728	LogS
Caco-2 Permeability	1.3422	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.0085	LD50, mol/kg
Fish Toxicity	2.4117	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.6666	pIGC50, ug/L

From admetSAR

Route of Exposure	Dermal ; ingestion
Mechanism of Toxicity	2-Phenoxyethanol is a glycol ether. Glycol ethers can produce toxicity following oxidation to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. 2-Phenoxyethanol causes reduction of NMDA-induced membrane currents, indicating a neurotoxic potential for 2-phenoxyethanol.
Metabolism	Oxidized to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively.
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)	No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference	Lockley DJ, Howes D, Williams FM: Cutaneous metabolism of glycol ethers. Arch Toxicol. 2005 Mar;79(3):160-8. Epub 2004 Nov 17.[15551062 ] Musshoff U, Madeja M, Binding N, Witting U, Speckmann EJ: Effects of 2-phenoxyethanol on N-methyl-D-aspartate (NMDA) receptor-mediated ion currents. Arch Toxicol. 1999 Feb;73(1):55-9.[10207615 ]

From T3DB

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Phenol ethers
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Phenol ethers
Alternative Parents	Alkyl aryl ethers Primary alcohols Hydrocarbon derivatives
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	Phenoxy compound - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

From ClassyFire

General Function:: Zinc ion binding
Specific Function:: NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of subunits.
Gene Name:: GRIN2A
Uniprot ID:: Q12879
Molecular Weight:: 165281.215 Da

Musshoff U, Madeja M, Binding N, Witting U, Speckmann EJ: Effects of 2-phenoxyethanol on N-methyl-D-aspartate (NMDA) receptor-mediated ion currents. Arch Toxicol. 1999 Feb;73(1):55-9. [10207615 ]

General Function:: Transferase activity
Specific Function:: Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:: CD38
Uniprot ID:: P28907
Molecular Weight:: 34328.145 Da

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

From T3DB