LAUROYL SARCOSINE

General Information

Mainterm	LAUROYL SARCOSINE
CAS Reg.No.(or other ID)	97-78-9
Regnum	177.1200 178.3130

From www.fda.gov

Computed Descriptors

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2D Structure
CID	7348
IUPAC Name	2-[dodecanoyl(methyl)amino]acetic acid
InChI	InChI=1S/C15H29NO3/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19/h3-13H2,1-2H3,(H,18,19)
InChI Key	BACYUWVYYTXETD-UHFFFAOYSA-N
Canonical SMILES	CCCCCCCCCCCC(=O)N(C)CC(=O)O
Molecular Formula	C15H29NO3
Wikipedia	lauroyl sarcosine

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	271.401
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	12
Complexity	254.0
CACTVS Substructure Key Fingerprint	A A A D c e B y 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 A A A A A A A A A A A A A A A A A H g A A C A A A C A D B g A Q C C A M A A g A I A A G Q G A A A A A A A A A A A A A G I A A A C A B I A g C A E A A A A B g C Q A A E Y i I C 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	57.6
Monoisotopic Mass	271.215
Exact Mass	271.215
XLogP3	None
XLogP3-AA	4.5
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	19
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

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9716
Human Intestinal Absorption	HIA+	0.9624
Caco-2 Permeability	Caco2+	0.6346
P-glycoprotein Substrate	Non-substrate	0.5548
P-glycoprotein Inhibitor	Non-inhibitor	0.8186
P-glycoprotein Inhibitor	Non-inhibitor	0.9309
Renal Organic Cation Transporter	Non-inhibitor	0.8906
Distribution
Subcellular localization	Mitochondria	0.6240
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8290
CYP450 2D6 Substrate	Non-substrate	0.7956
CYP450 3A4 Substrate	Non-substrate	0.5497
CYP450 1A2 Inhibitor	Non-inhibitor	0.8423
CYP450 2C9 Inhibitor	Non-inhibitor	0.9275
CYP450 2D6 Inhibitor	Non-inhibitor	0.9251
CYP450 2C19 Inhibitor	Non-inhibitor	0.8909
CYP450 3A4 Inhibitor	Non-inhibitor	0.9214
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9854
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9748
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9316
AMES Toxicity	Non AMES toxic	0.8963
Carcinogens	Non-carcinogens	0.7701
Fish Toxicity	Low FHMT	0.7256
Tetrahymena Pyriformis Toxicity	Low TPT	0.5721
Honey Bee Toxicity	Low HBT	0.7601
Biodegradation	Ready biodegradable	0.7753
Acute Oral Toxicity	III	0.6820
Carcinogenicity (Three-class)	Non-required	0.6661

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-1.3059	LogS
Caco-2 Permeability	0.9340	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.6563	LD50, mol/kg
Fish Toxicity	2.0976	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.1731	pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure	Oral ; inhalation ; dermal
Mechanism of Toxicity	While acyl sarcosines themselves are not toxic, they are nitrosating agents. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms.
Metabolism	Acyl sarcosines can be absorbed following oral or dermal contact, while nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase.
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)	No indication of carcinogenicity (not listed by IARC).
Minimum Risk Level
Health Effects	Acyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (A2881)
Treatment
Reference	Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503.[17485391 ] Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23.[18218609 ] Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407.[15380096 ] Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14.[11358107 ]

From T3DB

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Subclass	Amino acids, peptides, and analogues
Intermediate Tree Nodes	Amino acids and derivatives - Alpha amino acids and derivatives - N-acyl-alpha amino acids and derivatives
Direct Parent	N-acyl-alpha amino acids
Alternative Parents	Organopnictogen compounds Monocarboxylic acids and derivatives Carboxylic acids Hydrocarbon derivatives N-acyl amines Organic oxides Carbonyl compounds Organonitrogen compounds Tertiary carboxylic acid amides
Molecular Framework	Aliphatic acyclic compounds
Substituents	N-acyl-alpha-amino acid - N-acyl-amine - Tertiary carboxylic acid amide - Carboxamide group - Monocarboxylic acid or derivatives - Carboxylic acid - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

From ClassyFire

Targets

Target Details

Transient receptor potential cation channel subfamily A member 1

General Function:: Temperature-gated cation channel activity
Specific Function:: Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:: TRPA1
Uniprot ID:: O75762
Molecular Weight:: 127499.88 Da

References

Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]

Target Details

Retinoic acid receptor alpha

General Function:: Zinc ion binding
Specific Function:: Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
Gene Name:: RARA
Uniprot ID:: P10276
Molecular Weight:: 50770.805 Da

References

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 ]

Target Details

Peroxisome proliferator-activated receptor gamma

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:: PPARG
Uniprot ID:: P37231
Molecular Weight:: 57619.58 Da

References

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