ANILINE

General Information

Mainterm	ANILINE
CAS Reg.No.(or other ID)	62-53-3
Regnum	177.2600

From www.fda.gov

Computed Descriptors

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2D Structure
CID	6115
IUPAC Name	aniline
InChI	InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
InChI Key	PAYRUJLWNCNPSJ-UHFFFAOYSA-N
Canonical SMILES	C1=CC=C(C=C1)N
Molecular Formula	C6H7N
Wikipedia	aniline

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	93.129
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Complexity	46.1
CACTVS Substructure Key Fingerprint	A A A D c Y B i 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 w A A A A A A A A A A A B A A A A H A A Q A A A A C A i B E A A w w I B A A A C A A C R C Q A C C A A A g A g A I i A A A Z I g I I C K A k Z G A I A B g k A A I y A c 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 A = =
Topological Polar Surface Area	26.0
Monoisotopic Mass	93.058
Exact Mass	93.058
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	7
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

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9546
Human Intestinal Absorption	HIA+	0.9849
Caco-2 Permeability	Caco2+	0.8816
P-glycoprotein Substrate	Non-substrate	0.8908
P-glycoprotein Inhibitor	Non-inhibitor	0.9864
P-glycoprotein Inhibitor	Non-inhibitor	0.9856
Renal Organic Cation Transporter	Non-inhibitor	0.8716
Distribution
Subcellular localization	Lysosome	0.8707
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8594
CYP450 2D6 Substrate	Non-substrate	0.9116
CYP450 3A4 Substrate	Non-substrate	0.8107
CYP450 1A2 Inhibitor	Non-inhibitor	0.5372
CYP450 2C9 Inhibitor	Non-inhibitor	0.7538
CYP450 2D6 Inhibitor	Non-inhibitor	0.8890
CYP450 2C19 Inhibitor	Non-inhibitor	0.6150
CYP450 3A4 Inhibitor	Non-inhibitor	0.9558
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.7944
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9567
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9589
AMES Toxicity	Non AMES toxic	0.7047
Carcinogens	Carcinogens	0.5000
Fish Toxicity	High FHMT	0.5725
Tetrahymena Pyriformis Toxicity	High TPT	0.8900
Honey Bee Toxicity	Low HBT	0.6075
Biodegradation	Not ready biodegradable	0.5917
Acute Oral Toxicity	II	0.7555
Carcinogenicity (Three-class)	Non-required	0.6776

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-0.5705	LogS
Caco-2 Permeability	1.7796	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.5399	LD50, mol/kg
Fish Toxicity	1.8962	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.3551	pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure	Toxic by ingestion and a skin and eye irritant.
Mechanism of Toxicity	Aniline induces lipid peroxidation and protein oxidation in the spleen and that oxidative stress plays a role in the splenic toxicity of aniline. The hematopoietic system is the primary target of aniline insult in rats which is characterized by methemoglobinemia, hemolysis, and hemolytic anemia and by the development of splenic hyperplasia, siderosis, fibrosis, a variety of sarcomas, and, most commonly, fibrosarcomas on prolonged exposure. Many of the characteristics of splenotoxicity in rats, such as hyperplasia, hyperpigmentation, and/or formation of highly malignant tumors such as fibrosarcomas, are not restricted to aniline exposure, but also occur when animals are exposed to substituted anilines such as chloroaniline. Studies with aniline hydrochloride in rats indicate an association between erythrocyte damage and the severity of the splenotoxicity. Since one of the major functions of the spleen is to remove damaged erythrocytes, aniline-damaged erythrocytes would be expected to be scavenged by the spleen, especially by phagocytes. The deposition and subsequent breakdown of damaged erythrocytes will not only release aniline and/or its metabolites, but, most importantly, will also result in accumulation of iron in the spleen which may catalyze the generation of tissue-damaging oxygen radicals which can subsequently cause oxidation of biomolecules and result in lipid peroxidation and protein oxidation. It is also possible that during the scavenging of damaged erythrocytes, the splenic phagocytes, especially macrophages themselves, can become activated and release reactive oxygen species (ROS) which could further contribute to the oxidation of biomolecules leading to tissue injury.
Metabolism	None
Toxicity Values	None
Lethal Dose	None
Carcinogenicity (IARC Classification)	3, not classifiable as to its carcinogenicity to humans.
Minimum Risk Level	None
Health Effects	None
Treatment	None
Reference	Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504.[10570033 ] Bomhard EM, Herbold BA: Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol. 2005 Dec;35(10):783-835.[16468500 ] Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, Leclaire J: Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett. 2005 Sep 15;158(3):196-212.[15890478 ] Weiss T, Angerer J: Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Oct 5;778(1-2):179-92.[12376125 ] Hein DW, Doll MA, Xiao GH, Feng Y: Prostate expression of N-acetyltransferase 1 (NAT1) and 2 (NAT2) in rapid and slow acetylator congenic Syrian hamster. Pharmacogenetics. 2003 Mar;13(3):159-67.[12618593 ] Kuo HM, Ho HJ, Chao PD, Chung JG: Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. Phytomedicine. 2002 Oct;9(7):625-31.[12487326 ] Faraglia B, Chen SY, Gammon MD, Zhang Y, Teitelbaum SL, Neugut AI, Ahsan H, Garbowski GC, Hibshoosh H, Lin D, Kadlubar FF, Santella RM: Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke. Carcinogenesis. 2003 Apr;24(4):719-25.[12727801 ] Peluso M, Airoldi L, Magagnotti C, Fiorini L, Munnia A, Hautefeuille A, Malaveille C, Vineis P: White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. Carcinogenesis. 2000 Feb;21(2):183-7.[10657956 ] el-Bayoumy K, Donahue JM, Hecht SS, Hoffmann D: Identification and quantitative determination of aniline and toluidines in human urine. Cancer Res. 1986 Dec;46(12 Pt 1):6064-7.[3779628 ] Iwersen-Bergmann S, Schmoldt A: Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. Int J Legal Med. 2000;113(3):171-4.[10876991 ] Gan J, Skipper PL, Gago-Dominguez M, Arakawa K, Ross RK, Yu MC, Tannenbaum SR: Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer. J Natl Cancer Inst. 2004 Oct 6;96(19):1425-31.[15467031 ] Stanley LA, Coroneos E, Cuff R, Hickman D, Ward A, Sim E: Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J Histochem Cytochem. 1996 Sep;44(9):1059-67.[8773572 ] Vaziri SA, Hughes NC, Sampson H, Darlington G, Jewett MA, Grant DM: Variation in enzymes of arylamine procarcinogen biotransformation among bladder cancer patients and control subjects. Pharmacogenetics. 2001 Feb;11(1):7-20.[11207033 ] Khan MF, Boor PJ, Gu Y, Alcock NW, Ansari GA: Oxidative stress in the splenotoxicity of aniline. Fundam Appl Toxicol. 1997 Jan;35(1):22-30.[9024670 ]

From T3DB

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Benzene and substituted derivatives
Subclass	Aniline and substituted anilines
Intermediate Tree Nodes	Not available
Direct Parent	Aniline and substituted anilines
Alternative Parents	Organopnictogen compounds Hydrocarbon derivatives Primary amines
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

From ClassyFire

Targets

Target Details

Fas-binding factor 1

Specific Function:: Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
Gene Name:: FBF1
Uniprot ID:: Q8TES7
Molecular Weight:: 125445.19 Da

References

Thier R, Lewalter J, Selinski S, Bolt HM: Biological monitoring in workers in a nitrobenzene reduction plant: haemoglobin versus serum albumin adducts. Int Arch Occup Environ Health. 2001 Sep;74(7):483-8. [11697451 ]

Target Details

Kallikrein-1

General Function:: Serine-type endopeptidase activity
Specific Function:: Glandular kallikreins cleave Met-Lys and Arg-Ser bonds in kininogen to release Lys-bradykinin.
Gene Name:: KLK1
Uniprot ID:: P06870
Molecular Weight:: 28889.425 Da

References

Sousa MO, Miranda TL, Costa EB, Bittar ER, Santoro MM, Figueiredo AF: Linear competitive inhibition of human tissue kallikrein by 4-aminobenzamidine and benzamidine and linear mixed inhibition by 4-nitroaniline and aniline. Braz J Med Biol Res. 2001 Jan;34(1):35-44. [11151026 ]

Target Details

Serum albumin

General Function:: Toxic substance binding
Specific Function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:: ALB
Uniprot ID:: P02768
Molecular Weight:: 69365.94 Da

From T3DB