4,4'-METHYLENEDIANILINE
General Information
| Mainterm | 4,4'-METHYLENEDIANILINE |
| CAS Reg.No.(or other ID) | 101-77-9 |
| Regnum |
177.2800 175.300 177.2600 177.2280 177.1680 177.2450 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 7577 |
| IUPAC Name | 4-[(4-aminophenyl)methyl]aniline |
| InChI | InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2 |
| InChI Key | YBRVSVVVWCFQMG-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC(=CC=C1CC2=CC=C(C=C2)N)N |
| Molecular Formula | C13H14N2 |
| Wikipedia | 4,4′-methylenedianiline |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 198.269 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 157.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B z 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 A B Q A A A H A A Q A A A A D A i B G A A w w I B A A A C A A i 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 g M A O C A A A A A A A A A A Q A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 52.0 |
| Monoisotopic Mass | 198.116 |
| Exact Mass | 198.116 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.9562 |
| Human Intestinal Absorption | HIA+ | 0.9211 |
| Caco-2 Permeability | Caco2+ | 0.7730 |
| P-glycoprotein Substrate | Non-substrate | 0.7876 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9332 |
| Non-inhibitor | 0.8609 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8068 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5978 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8384 |
| CYP450 2D6 Substrate | Non-substrate | 0.8153 |
| CYP450 3A4 Substrate | Non-substrate | 0.8230 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7607 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8879 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7827 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8583 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5704 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8653 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9598 |
| Non-inhibitor | 0.8469 | |
| AMES Toxicity | AMES toxic | 0.9108 |
| Carcinogens | Carcinogens | 0.6333 |
| Fish Toxicity | High FHMT | 0.8593 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9652 |
| Honey Bee Toxicity | Low HBT | 0.7455 |
| Biodegradation | Not ready biodegradable | 0.9812 |
| Acute Oral Toxicity | III | 0.8430 |
| Carcinogenicity (Three-class) | Non-required | 0.4538 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4913 | LogS |
| Caco-2 Permeability | 1.4285 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6151 | LD50, mol/kg |
| Fish Toxicity | 1.1032 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7033 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Inhalation, oral, dermal |
|---|---|
| Mechanism of Toxicity | After 4,4'-Methylenedianiline enters to our body, it is transported in the blood or stored in tissues. The N-N-acetylation of the compound leads to the formation of some toxic derivatives. The liver and thyroid are the targets of 4,4'-methylenedianiline in animals. |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Diphenylmethanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diphenylmethanes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Diphenylmethane - 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 diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. |
From ClassyFire
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity).Isoform 1 is critical for hindlimb motor control and for the differentiation of amacrine and horizontal cells in the retina. Regulates the expression of PTF1A synergistically with FOXN4 (By similarity).
- Gene Name:
- RORB
- Uniprot ID:
- Q92753
- Molecular Weight:
- 53219.385 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 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 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 ]
From T3DB