Human Metabolome Database: Showing metabocard for Aniline (HMDB0003012)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (27) Show 27 proteins XML

enzymes (27) Show 27 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:26 UTC

Update Date

2020-02-26 21:24:20 UTC

HMDB ID

HMDB0003012

Secondary Accession Numbers

HMDB03012

Metabolite Identification

Common Name

Aniline

Description

Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aminobenzene	ChEBI
Aminophen	ChEBI
Anilin	ChEBI
Benzenamine	ChEBI
Benzeneamine	ChEBI
Kyanol	ChEBI
Phenylamine	ChEBI
Arylamine	Kegg
Anilina	HMDB
Aniline hydrobromide	HMDB
Aniline reagent	HMDB
Anyvim	HMDB
Benzidam	HMDB
Cyanol	HMDB
D'Aniline	HMDB
Krystallin	HMDB
Aniline diphosphate (3:1)	HMDB
Aniline hydrogen iodide	HMDB
Aniline phosphate (1:2)	HMDB
Aniline phosphate (2:1)	HMDB
Aniline sulfate	HMDB
Aniline, 3-(13)C-labeled CPD	HMDB
Aniline aluminium salt	HMDB
Aniline diphosphate (4:1)	HMDB
Aniline hydrochloride-(15)N-labeled CPD	HMDB
Aniline hydrofluoride	HMDB
Aniline monosulfate	HMDB
Aniline nitrate	HMDB
Aniline sulfate (2:1)	HMDB
Aniline, 2-(13)C-labeled CPD	HMDB
Aniline, conjugate acid	HMDB
Aniline, sodium salt	HMDB
Aniline dihydrofluoride	HMDB
Aniline diphosphate (1:1)	HMDB
Aniline hydrochloride	HMDB
Aniline hydrochloride-(14)C-labeled CPD	HMDB
Aniline perchlorate	HMDB
Aniline phosphonate (1:1)	HMDB
Aniline, (13)C-labeled CPD	HMDB
Aniline, (14)C-labeled CPD	HMDB
Aniline, 4-(13)C-labeled CPD	HMDB
Aniline, ion(1+)	HMDB
Aniline, monolithium salt	HMDB
Aniline phosphate (1:1)	HMDB
Aniline sulfate (2:1), (14)C-labeled CPD	HMDB
Aniline, 15N-labeled CPD	HMDB
Aniline, 3H-labeled CPD	HMDB
Aniline, magnesium (1:1) salt	HMDB

Chemical Formula

C₆H₇N

Average Molecular Weight

93.1265

Monoisotopic Molecular Weight

93.057849229

IUPAC Name

aniline

Traditional Name

aniline

CAS Registry Number

62-53-3

SMILES

NC1=CC=CC=C1

InChI Identifier

InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

InChI Key

PAYRUJLWNCNPSJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary arylamine (CHEBI:17296 )
anilines (CHEBI:17296 )
an arylamine (ANILINE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Tissue and substructures:

Epidermis

Biofluid and excreta:

Urine

Organ and components:

Role

Environmental role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	36 mg/mL at 25 °C	Not Available
LogP	0.90	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	18 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.14	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.76 m³·mol⁻¹	ChemAxon
Polarizability	10.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-9a543eee5081cc927e82	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e04550d3cafee77e6192	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-b4213ef5f8ee4a3df612	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1900000000-b5d970641bbe63fdb366	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-9a543eee5081cc927e82	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e04550d3cafee77e6192	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-b4213ef5f8ee4a3df612	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1900000000-b5d970641bbe63fdb366	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-62eb000567821fbe8a22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-0900000000-ed34a4f0bafc3ce06174	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-a23bad3a5415210b8e58	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-129ed2147aba87164399	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-9000000000-9e60a29bae11a3beb396	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kf-9000000000-8e5e6fec72fd720bd3bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0006-9000000000-e04550d3cafee77e6192	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-9000000000-4a2ea8998eab06e3b7fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-002f-9000000000-041fc0d729e6308b36ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-004i-9000000000-c0f67277e0af76d5d6e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0fb9-9000000000-35b2093eb2c81ba07d17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-15d86b7cf94658003a7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-9000000000-fc34fd188d386065c4f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03dl-9000000000-fbed3991af3afeea3a79	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9000000000-0bea53746f5bc30ab770	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0007-9000000000-971619ea8bd73637ba14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-2001822055db683e8999	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0006-9000000000-a5bc25b5010f2044b435	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0006-9000000000-8ab282b725391b0d9923	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-4a2ea8998eab06e3b7fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002f-9000000000-041fc0d729e6308b36ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-c0f67277e0af76d5d6e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fb9-9000000000-35b2093eb2c81ba07d17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-15d86b7cf94658003a7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9000000000-fc34fd188d386065c4f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03dl-9000000000-fbed3991af3afeea3a79	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9000000000-4ba5d22a406245826ca0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Bladder
Epidermis
Prostate
Spleen

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	<1 nmol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06728

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003571

KNApSAcK ID

Not Available

Chemspider ID

5889

KEGG Compound ID

C00292

BioCyc ID

ANILINE

BiGG ID

Not Available

Wikipedia Link

Aniline

METLIN ID

489

PubChem Compound

6115

PDB ID

Not Available

ChEBI ID

17296

Food Biomarker Ontology

Not Available

VMH ID

M01341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:3779628 ]
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. [PubMed: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. [PubMed:16468500 ]
Iwersen-Bergmann S, Schmoldt A: Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. Int J Legal Med. 2000;113(3):171-4. [PubMed: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. [PubMed:15467031 ]
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. [PubMed:15890478 ]
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. [PubMed: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. [PubMed:11207033 ]

Only showing the first 10 proteins. There are 27 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Arylamine N-acetyltransferase 1

General function:: Involved in acetyltransferase activity
Specific function:: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:: NAT1
Uniprot ID:: P18440
Molecular weight:: 33898.445

Enzyme Details

2. Arylamine N-acetyltransferase 2

General function:: Involved in acetyltransferase activity
Specific function:: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:: NAT2
Uniprot ID:: P11245
Molecular weight:: 33570.245

Enzyme Details

3. Arylacetamide deacetylase

General function:: Involved in hydrolase activity
Specific function:: Arylacetamide deacetylation is an important enzyme activity in the metabolic activation of arylamine substrates to ultimate carcinogens. Displays major serine hydrolase activity in liver microsomes. Hydrolyzes also flutamide, which is an antiandrogen drug used for the treatment of prostate cancer that occasionally causes severe hepatotoxicity. Displays cellular triglyceride lipase activity in liver. Increases intracellular fatty acids derived from hydrolysis of newly formed triglyceride stores.
Gene Name:: AADAC
Uniprot ID:: P22760
Molecular weight:: 45733.28

Enzyme Details

4. Arylamine N-acetyltransferase 2