T3DB: Metenamine

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Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-09-11 05:18:28 UTC

Update Date

2014-12-24 20:26:57 UTC

Accession Number

T3D4834

Identification

Common Name

Metenamine

Class

Small Molecule

Description

Metenamine belongs to the family of Aminals. These are organic compounds containing the aminal functional group. Metenamine is an antimicrobial food preservative, but is of limited use and usage is declining. It is used to prevent "late blowing" of hard cheese by inhibiting growth of unwanted bacteria. Presently (2002) its European use is limited to one type of Italian cheese, Provolone. It acts by releasing formaldehyde under acidic conditions.

Compound Type

Amine
Food Additive
Food Toxin
Household Toxin
Metabolite
Organic Compound
Preservative
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
1,3,5,7-Tetraazaadamantane
1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodide
1,3,5,7-Tetraazatricyclo(3.3.1.137)decane
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane
1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1~3,7~]decane
Aceto HMT
Aminoform
Aminoformaldehyde
Ammoform
Ammonioformaldehyde
Antihydral
Carin
Cystamin
Cystogen
Duirexol
E239
Ekagom h
Esametilentetramina
Formaldehyde-ammonia 6:4
Formamine
Formin
Formin (heterocycle)
Formin (the heterocyclic compound)
Grasselerator 102
H.m.t.
Herax UTS
Heterin
HEX
Hexa
Hexa (vulcanization accelerator)
Hexa-flo-pulver
Hexaform
Hexaloids
Hexamethylamine
Hexamethylenamine
Hexamethylene tetramine
Hexamethyleneamine
Hexamethylenetetraamine
Hexamethylenetetramine
Hexamethylenetetramine (aliphatic)
Hexamethylenetetramine, 8CI
Hexamethylenetetramine, acs
Hexamethylenetetramine-palladium chloride adduct
Hexamethylenetetraminum
Hexamethylentetramin
Hexamethylentetramine
Hexamethylentetraminum
Hexamine
Hexamine (heterocycle)
Hexamine silver
Hexaminum
Hexasan
Hexilmethylenamine
HMT
HMTA
Mandelamine
Metenamina
Methamin
Methenamin
Methenamine
Methenamine silver
Methenaminum
Metramine
Naphthamine
Natasol fast orange GR salt
Nocceler H
Preparation af
Resotropin
S 4 (Heterocycle)
Sanceler h
Silver methenamine
Tetraazaadamantane
Uramin
Uratrine
Urisol
Uritone
Uro-phosphate
Urodeine
Urotropin
Urotropine
Vesaloin
Vesalvine
Vulkacit H 30
Vulkacit H30
Xametrin
[16]-Adamazane, INN

Chemical Formula

C₆H₁₂N₄

Average Molecular Mass

140.186 g/mol

Monoisotopic Mass

140.106 g/mol

CAS Registry Number

100-97-0

IUPAC Name

1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane

Traditional Name

1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane

SMILES

C1N2CN3CN1CN(C2)C3

InChI Identifier

InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

InChI Key

InChIKey=VKYKSIONXSXAKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazinanes

Sub Class

1,3,5-triazinanes

Direct Parent

1,3,5-triazinanes

Alternative Parents

Substituents

1,3,5-triazinane
Azacycle
Aminal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

polycyclic cage (CHEBI:6824 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	> 250 °C
Boiling Point	Not Available
Solubility	449 mg/mL at 12 °C
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	766 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	0.39	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Basic)	5.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.96 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37 m³·mol⁻¹	ChemAxon
Polarizability	14.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-37095c7b831e11e5eee2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-05c8e159897335060443	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ox-2900000000-86fe33e31cc8f7108c14	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ti-9300000000-7eb44254c8cc65c09acd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-fd4edf8f48f9c42bca0c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004l-9000000000-371b89c99afba4931848	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-fdd6b719cb07e4102442	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-fdd6b719cb07e4102442	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-fdd6b719cb07e4102442	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-4c20ce3a6256ce9cf869	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-4c20ce3a6256ce9cf869	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-4c20ce3a6256ce9cf869	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-df90583457c277060500	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-df90583457c277060500	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-df90583457c277060500	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-96b1ccc7b2dbac963a64	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-96b1ccc7b2dbac963a64	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-96b1ccc7b2dbac963a64	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9300000000-e762ea01823717c4bda9	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

6824

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4834.pdf

General References

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Nuclear factor erythroid 2-related factor 2

General Function:: Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
Specific Function:: Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
Gene Name:: NFE2L2
Uniprot ID:: Q16236
Molecular Weight:: 67825.9 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.45 uM	ATG_NRF2_ARE_CIS	Attagene

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 ]

Metenamine (T3D4834)

Structure for T3D4834: Metenamine

Targets

Binding/Activity Constants

References