1-Methylnaphthalene
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | 1-Methylnaphthalene |
| CAS number | 90-12-0 |
| COE number | 11009 |
| JECFA number | 1335 |
| Flavouring type | substances |
| FL No. | 01.014 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 7002 |
| IUPAC Name | 1-methylnaphthalene |
| InChI | InChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3 |
| InChI Key | QPUYECUOLPXSFR-UHFFFAOYSA-N |
| Canonical SMILES | CC1=CC=CC2=CC=CC=C12 |
| Molecular Formula | C11H10 |
| Wikipedia | 1-methylnaphthalene |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 142.201 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 128.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w 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 Y A A A A A A A A A D B U A A A G A A A A A A A D A C A G A A y A M A A A A C A A i B C A A A C A A A g A A A I i A A A A I g I I C K A E R C A I A A g g A A I i A c A g M A O g A A C A A A Q A A A A A A Q A A C A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 0.0 |
| Monoisotopic Mass | 142.078 |
| Exact Mass | 142.078 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.9704 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8466 |
| P-glycoprotein Substrate | Non-substrate | 0.6749 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8994 |
| Non-inhibitor | 0.9221 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8256 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.8258 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7485 |
| CYP450 2D6 Substrate | Non-substrate | 0.8811 |
| CYP450 3A4 Substrate | Non-substrate | 0.7344 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7333 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9359 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8710 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5448 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9225 |
| Non-inhibitor | 0.8881 | |
| AMES Toxicity | AMES toxic | 0.9108 |
| Carcinogens | Non-carcinogens | 0.6897 |
| Fish Toxicity | High FHMT | 0.9385 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9975 |
| Honey Bee Toxicity | High HBT | 0.7646 |
| Biodegradation | Not ready biodegradable | 0.8795 |
| Acute Oral Toxicity | III | 0.7963 |
| Carcinogenicity (Three-class) | Warning | 0.4452 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.8273 | LogS |
| Caco-2 Permeability | 1.8758 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9099 | LD50, mol/kg |
| Fish Toxicity | 0.6527 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2969 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral ; inhalation |
|---|---|
| Mechanism of Toxicity | The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. |
| Metabolism | PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. |
| Toxicity Values | LD50: 1840 mg/kg (Oral, Rat) |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10) |
| Treatment | There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthalenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings. |
From ClassyFire
Targets
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Wikipedia. Benzopyrene. Last Updated 22 January 2009. : http://en.wikipedia.org/wiki/Benzopyrene [11460716 ]
- General Function:
- Glycine n-methyltransferase activity
- Specific Function:
- Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
- Gene Name:
- GNMT
- Uniprot ID:
- Q14749
- Molecular Weight:
- 32742.0 Da
References
- Wikipedia. Benzopyrene. Last Updated 22 January 2009. : http://en.wikipedia.org/wiki/Benzopyrene [11460716 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Korhonen LE, Rahnasto M, Mahonen NJ, Wittekindt C, Poso A, Juvonen RO, Raunio H: Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15. [15916432 ]
- Gene Name:
- TP53
- Uniprot ID:
- P04637
- Molecular Weight:
- 43652.79 Da
From T3DB