ALPHA-TOCOPHEROL ACETATE
General Information
| Mainterm | ALPHA-TOCOPHEROL ACETATE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 58-95-7 |
| Regnum |
172.480 182.8892 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 86472 |
| IUPAC Name | [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate |
| InChI | InChI=1S/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1 |
| InChI Key | ZAKOWWREFLAJOT-CEFNRUSXSA-N |
| Canonical SMILES | CC1=C2C(=C(C(=C1C)OC(=O)C)C)CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C |
| Molecular Formula | C31H52O3 |
| Wikipedia | DL-α-tocopherol acetate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 472.754 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 14 |
| Complexity | 602.0 |
| CACTVS Substructure Key Fingerprint | A A A D c f B 4 M 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 0 Q A A A A A A A A A C R A A A A G g A A A A A A D U S A m A A C D o A A B A C I A g D Q C A A C C A A g I A A A i A A E C I g M J i K E M B q C O i C k w B E I q A f A w P A O w Q A D A A A Y A A C C A A Y A A D A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 35.5 |
| Monoisotopic Mass | 472.392 |
| Exact Mass | 472.392 |
| XLogP3 | None |
| XLogP3-AA | 10.8 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 34 |
| Defined Atom Stereocenter Count | 3 |
| 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+ | 0.9442 |
| Human Intestinal Absorption | HIA+ | 0.9920 |
| Caco-2 Permeability | Caco2+ | 0.7984 |
| P-glycoprotein Substrate | Substrate | 0.7305 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6600 |
| Inhibitor | 0.8927 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8112 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7985 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7680 |
| CYP450 2D6 Substrate | Non-substrate | 0.8069 |
| CYP450 3A4 Substrate | Substrate | 0.7228 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7411 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6844 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9106 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5752 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8527 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8053 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8849 |
| Non-inhibitor | 0.7016 | |
| AMES Toxicity | Non AMES toxic | 0.9275 |
| Carcinogens | Non-carcinogens | 0.8845 |
| Fish Toxicity | High FHMT | 0.9904 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9982 |
| Honey Bee Toxicity | High HBT | 0.7893 |
| Biodegradation | Not ready biodegradable | 0.9929 |
| Acute Oral Toxicity | IV | 0.6347 |
| Carcinogenicity (Three-class) | Non-required | 0.7227 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.4682 | LogS |
| Caco-2 Permeability | 1.1836 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5022 | LD50, mol/kg |
| Fish Toxicity | -0.5134 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 2.1157 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Quinone and hydroquinone lipids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vitamin E compounds |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Diterpenoid - Chromane - Benzopyran - 1-benzopyran - Alkyl aryl ether - Benzenoid - Carboxylic acid ester - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as vitamin e compounds. These are a group of fat-soluble compounds containing or derived either from a tocopherol or a tocotrienol skeleton. |
From ClassyFire
Targets
- General Function:
- Transporter activity
- Specific Function:
- Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.
- Gene Name:
- SEC14L4
- Uniprot ID:
- Q9UDX3
- Molecular Weight:
- 46643.385 Da
- General Function:
- Transporter activity
- Specific Function:
- Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.
- Gene Name:
- SEC14L3
- Uniprot ID:
- Q9UDX4
- Molecular Weight:
- 46047.835 Da
- General Function:
- Vitamin e binding
- Specific Function:
- Carrier protein. Binds to some hydrophobic molecules and promotes their transfer between the different cellular sites. Binds with high affinity to alpha-tocopherol. Also binds with a weaker affinity to other tocopherols and to tocotrienols. May have a transcriptional activatory activity via its association with alpha-tocopherol. Probably recognizes and binds some squalene structure, suggesting that it may regulate cholesterol biosynthesis by increasing the transfer of squalene to a metabolic active pool in the cell.
- Gene Name:
- SEC14L2
- Uniprot ID:
- O76054
- Molecular Weight:
- 46144.9 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase involved in various cellular processes such as regulation of the B-cell receptor (BCR) signalosome, oxidative stress-induced apoptosis, androgen receptor-dependent transcription regulation, insulin signaling and endothelial cells proliferation. Plays a key role in B-cell activation by regulating BCR-induced NF-kappa-B activation. Mediates the activation of the canonical NF-kappa-B pathway (NFKB1) by direct phosphorylation of CARD11/CARMA1 at 'Ser-559', 'Ser-644' and 'Ser-652'. Phosphorylation induces CARD11/CARMA1 association with lipid rafts and recruitment of the BCL10-MALT1 complex as well as MAP3K7/TAK1, which then activates IKK complex, resulting in nuclear translocation and activation of NFKB1. Plays a direct role in the negative feedback regulation of the BCR signaling, by down-modulating BTK function via direct phosphorylation of BTK at 'Ser-180', which results in the alteration of BTK plasma membrane localization and in turn inhibition of BTK activity. Involved in apoptosis following oxidative damage: in case of oxidative conditions, specifically phosphorylates 'Ser-36' of isoform p66Shc of SHC1, leading to mitochondrial accumulation of p66Shc, where p66Shc acts as a reactive oxygen species producer. Acts as a coactivator of androgen receptor (ANDR)-dependent transcription, by being recruited to ANDR target genes and specifically mediating phosphorylation of 'Thr-6' of histone H3 (H3T6ph), a specific tag for epigenetic transcriptional activation that prevents demethylation of histone H3 'Lys-4' (H3K4me) by LSD1/KDM1A. In insulin signaling, may function downstream of IRS1 in muscle cells and mediate insulin-dependent DNA synthesis through the RAF1-MAPK/ERK signaling cascade. May participate in the regulation of glucose transport in adipocytes by negatively modulating the insulin-stimulated translocation of the glucose transporter SLC2A4/GLUT4. Under high glucose in pancreatic beta-cells, is probably involved in the inhibition of the insulin gene transcription, via regulation of MYC expression. In endothelial cells, activation of PRKCB induces increased phosphorylation of RB1, increased VEGFA-induced cell proliferation, and inhibits PI3K/AKT-dependent nitric oxide synthase (NOS3/eNOS) regulation by insulin, which causes endothelial dysfunction. Also involved in triglyceride homeostasis (By similarity). Phosphorylates ATF2 which promotes cooperation between ATF2 and JUN, activating transcription.
- Gene Name:
- PRKCB
- Uniprot ID:
- P05771
- Molecular Weight:
- 76868.45 Da
- General Function:
- Iron ion binding
- Specific Function:
- Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
- Gene Name:
- ALOX5
- Uniprot ID:
- P09917
- Molecular Weight:
- 77982.595 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differentiation, migration and adhesion, tumorigenesis, cardiac hypertrophy, angiogenesis, platelet function and inflammation, by directly phosphorylating targets such as RAF1, BCL2, CSPG4, TNNT2/CTNT, or activating signaling cascade involving MAPK1/3 (ERK1/2) and RAP1GAP. Involved in cell proliferation and cell growth arrest by positive and negative regulation of the cell cycle. Can promote cell growth by phosphorylating and activating RAF1, which mediates the activation of the MAPK/ERK signaling cascade, and/or by up-regulating CDKN1A, which facilitates active cyclin-dependent kinase (CDK) complex formation in glioma cells. In intestinal cells stimulated by the phorbol ester PMA, can trigger a cell cycle arrest program which is associated with the accumulation of the hyper-phosphorylated growth-suppressive form of RB1 and induction of the CDK inhibitors CDKN1A and CDKN1B. Exhibits anti-apoptotic function in glioma cells and protects them from apoptosis by suppressing the p53/TP53-mediated activation of IGFBP3, and in leukemia cells mediates anti-apoptotic action by phosphorylating BCL2. During macrophage differentiation induced by macrophage colony-stimulating factor (CSF1), is translocated to the nucleus and is associated with macrophage development. After wounding, translocates from focal contacts to lamellipodia and participates in the modulation of desmosomal adhesion. Plays a role in cell motility by phosphorylating CSPG4, which induces association of CSPG4 with extensive lamellipodia at the cell periphery and polarization of the cell accompanied by increases in cell motility. Is highly expressed in a number of cancer cells where it can act as a tumor promoter and is implicated in malignant phenotypes of several tumors such as gliomas and breast cancers. Negatively regulates myocardial contractility and positively regulates angiogenesis, platelet aggregation and thrombus formation in arteries. Mediates hypertrophic growth of neonatal cardiomyocytes, in part through a MAPK1/3 (ERK1/2)-dependent signaling pathway, and upon PMA treatment, is required to induce cardiomyocyte hypertrophy up to heart failure and death, by increasing protein synthesis, protein-DNA ratio and cell surface area. Regulates cardiomyocyte function by phosphorylating cardiac troponin T (TNNT2/CTNT), which induces significant reduction in actomyosin ATPase activity, myofilament calcium sensitivity and myocardial contractility. In angiogenesis, is required for full endothelial cell migration, adhesion to vitronectin (VTN), and vascular endothelial growth factor A (VEGFA)-dependent regulation of kinase activation and vascular tube formation. Involved in the stabilization of VEGFA mRNA at post-transcriptional level and mediates VEGFA-induced cell proliferation. In the regulation of calcium-induced platelet aggregation, mediates signals from the CD36/GP4 receptor for granule release, and activates the integrin heterodimer ITGA2B-ITGB3 through the RAP1GAP pathway for adhesion. During response to lipopolysaccharides (LPS), may regulate selective LPS-induced macrophage functions involved in host defense and inflammation. But in some inflammatory responses, may negatively regulate NF-kappa-B-induced genes, through IL1A-dependent induction of NF-kappa-B inhibitor alpha (NFKBIA/IKBA). Upon stimulation with 12-O-tetradecanoylphorbol-13-acetate (TPA), phosphorylates EIF4G1, which modulates EIF4G1 binding to MKNK1 and may be involved in the regulation of EIF4E phosphorylation. Phosphorylates KIT, leading to inhibition of KIT activity. Phosphorylates ATF2 which promotes cooperation between ATF2 and JUN, activating transcription.
- Gene Name:
- PRKCA
- Uniprot ID:
- P17252
- Molecular Weight:
- 76749.445 Da
- General Function:
- Phospholipid binding
- Specific Function:
- Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity.
- Gene Name:
- DGKA
- Uniprot ID:
- P23743
- Molecular Weight:
- 82629.55 Da
- General Function:
- Protein serine/threonine phosphatase activity
- Specific Function:
- PP2A can modulate the activity of phosphorylase B kinase casein kinase 2, mitogen-stimulated S6 kinase, and MAP-2 kinase.
- Gene Name:
- PPP2CB
- Uniprot ID:
- P62714
- Molecular Weight:
- 35574.85 Da
- General Function:
- PP2A is the major phosphatase for microtubule-associated proteins (MAPs). PP2A can modulate the activity of phosphorylase B kinase casein kinase 2, mitogen-stimulated S6 kinase, and MAP-2 kinase. Cooperates with SGO2 to protect centromeric cohesin from separase-mediated cleavage in oocytes specifically during meiosis I (By similarity). Can dephosphorylate SV40 large T antigen and p53/TP53. Activates RAF1 by dephosphorylating it at 'Ser-259'.
- Specific Function:
- Gaba receptor binding
- Gene Name:
- PPP2CA
- Uniprot ID:
- P67775
- Molecular Weight:
- 35593.93 Da
From T3DB