Metenamine
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Basic Info
| Common Name | Metenamine(F05536) |
| 2D Structure | |
| 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. |
| FRCD ID | F05536 |
| CAS Number | 100-97-0 |
| PubChem CID | 4101 |
| Formula | C6H12N4 |
| IUPAC Name | None |
| InChI Key | VKYKSIONXSXAKP-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 |
| Canonical SMILES | C1N2CN3CN1CN(C2)C3 |
| Isomeric SMILES | C1N2CN3CN1CN(C2)C3 |
| Synonyms |
methenamine
Hexamethylenetetramine
100-97-0
Hexamine
Urotropine
Hexamethylenamine
1,3,5,7-Tetraazaadamantane
Aminoform
Methenamin
Urotropin
|
| Classifies |
Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazinanes |
| Subclass | 1,3,5-triazinanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,3,5-triazinanes |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | 1,3,5-triazinane - Azacycle - Aminal - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aliphatic heteropolycyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 140.19 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Complexity | 84.8 |
| Monoisotopic Mass | 140.106 |
| Exact Mass | 140.106 |
| XLogP | 0.3 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9471 |
| Human Intestinal Absorption | HIA+ | 0.9512 |
| Caco-2 Permeability | Caco2+ | 0.6422 |
| P-glycoprotein Substrate | Non-substrate | 0.5751 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9010 |
| Non-inhibitor | 0.8233 | |
| Renal Organic Cation Transporter | Inhibitor | 0.5844 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4811 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9050 |
| CYP450 2D6 Substrate | Non-substrate | 0.5443 |
| CYP450 3A4 Substrate | Non-substrate | 0.7343 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7688 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9102 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9345 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9041 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9119 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5775 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7993 |
| Non-inhibitor | 0.8231 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.9039 |
| Fish Toxicity | Low FHMT | 0.8572 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5443 |
| Honey Bee Toxicity | Low HBT | 0.6625 |
| Biodegradation | Not ready biodegradable | 0.9559 |
| Acute Oral Toxicity | I | 0.7900 |
| Carcinogenicity (Three-class) | Non-required | 0.7096 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9589 | LogS |
| Caco-2 Permeability | 1.4964 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.8831 | LD50, mol/kg |
| Fish Toxicity | 4.5724 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3642 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Sweet potato starch residue as starting material to prepare polyacrylonitrileadsorbent via SI-SET-LRP. | J Agric Food Chem | 2014 Feb 26 | 24512626 |
| Multi-detection of preservatives in cheeses by liquid chromatography-tandem mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2012 Oct 1 | 22959825 |
| Conservation characteristics of wilted perennial ryegrass silage made usingbiological or chemical additives. | J Dairy Sci | 2010 Feb | 20105535 |
| Detection of sugar syrups in apple juice by delta(2)H per thousand and delta(13)Cper thousand analysis of hexamethylenetetramine prepared from fructose. | J Agric Food Chem | 2003 Mar 26 | 12643633 |
| Formaldehyde and hexamethylenetetramine as food additives: chemical interactions and toxicology. | Food Addit Contam | 1992 Sep-Oct | 1298665 |
| Oral toxicity of formaldehyde and its derivatives. | Crit Rev Toxicol | 1991 | 1741947 |
Targets
- 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
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 ]