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Thiomyristoyl - 10mM in DMSO, high purity , CAS No.1429749-41-6

    Grade & Purity:
  • 10mM in DMSO
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Item Number
T421586
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T421586-1ml
1ml
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$241.90

Sirtuin Inhibitors

Basic Description

Synonyms TMCarbamic acid,N-​[(1S)​-​1-​[(phenylamino)​carbonyl]​-​5-​[(1-​thioxotetradecyl)​amino]​pentyl]​-​,phenylmethyl ester
Specifications & Purity 10mM in DMSO
Biochemical and Physiological Mechanisms Thiomyristoyl (TM) is a potent and specific SIRT2 inhibitor with an IC50 of 28 nM. It inhibits SIRT1 with an IC50 value of 98 μM and does not inhibit SIRT3 even at 200 μM.
Storage Temp Store at -80°C
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Product Description

Information

Thiomyristoyl Thiomyristoyl (TM) is a potent and specific SIRT2 inhibitor with an IC50 of 28 nM. It inhibits SIRT1 with an IC50 value of 98 μM and does not inhibit SIRT3 even at 200 μM.

Targets

SIRT2 (Cell-free assay) 28 nM

In vitro

Thiomyristoyl(TM) is a highly selective SIRT2 inhibitor. It cannot efficiently inhibit SIRT3, SIRT5, SIRT6, or SIRT7. it shows great inhibition of cell viability and its cytotoxicity is relatively selective toward cancer cells. TM decreases c-Myc oncoprotein level in cancer cells, the ability of TM to decrease c-Myc abundance in different cell lines correlates with the sensitivity of the cell lines to TM.

In vivo

The anticancer effect of TM correlates with its ability to decrease c-Myc level. TM has limited effects on non-cancerous cells and tumor-free mice.

Cell Research(from reference)

Cell lines:breast cancer cell lines MCF-7 

Concentrations:1, 5, 10, 25, 50 μM 

Incubation Time:6 h 

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Organic acids and derivatives
Class Carboxylic acids and derivatives
Subclass Amino acids, peptides, and analogues
Intermediate Tree Nodes Amino acids and derivatives - Alpha amino acids and derivatives
Direct Parent Alpha amino acid amides
Alternative Parents Benzyloxycarbonyls  Anilides  N-arylamides  N-acyl amines  Thioamides  Carbamate esters  Organic carbonic acids and derivatives  Thiocarboxylic acid amides  Carboxylic acid amides  Organopnictogen compounds  Organooxygen compounds  Organic oxides  Hydrocarbon derivatives  
Molecular Framework Aromatic homomonocyclic compounds
Substituents Alpha-amino acid amide - Benzyloxycarbonyl - Anilide - N-arylamide - Fatty acyl - Benzenoid - N-acyl-amine - Fatty amide - Monocyclic benzene moiety - Carbamic acid ester - Thioamide - Carbonic acid derivative - Carboxamide group - Thiocarboxylic acid amide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aromatic homomonocyclic compound
Description This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
External Descriptors Not available

Product Properties

ALogP 9.441
HBD Count 3
Rotatable Bond 24

Associated Targets(Human)

SIRT2 Tchem NAD-dependent protein deacetylase sirtuin-2 (6 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
BXPC-3 (2997 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A549 (127892 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HeLa (62764 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI-H23 (49055 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT3 Tchem NAD-dependent deacetylase sirtuin 3 (1285 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SW948 (147 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT6 Tchem NAD-dependent protein deacetylase sirtuin-6 (671 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT5 Tchem NAD-dependent protein deacylase sirtuin-5, mitochondrial (1056 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SIRT2 Tchem Cereblon/NAD-dependent protein deacetylase sirtuin-2 (35 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

N2a (708 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name benzyl N-[(2S)-1-anilino-1-oxo-6-(tetradecanethioylamino)hexan-2-yl]carbamate
INCHI InChI=1S/C34H51N3O3S/c1-2-3-4-5-6-7-8-9-10-11-18-26-32(41)35-27-20-19-25-31(33(38)36-30-23-16-13-17-24-30)37-34(39)40-28-29-21-14-12-15-22-29/h12-17,21-24,31H,2-11,18-20,25-28H2,1H3,(H,35,41)(H,36,38)(H,37,39)/t31-/m0/s1
InChIKey CJQGLLUJIVNREL-HKBQPEDESA-N
Smiles CCCCCCCCCCCCCC(=S)NCCCCC(C(=O)NC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
Isomeric SMILES CCCCCCCCCCCCCC(=S)NCCCC[C@@H](C(=O)NC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
PubChem CID 126843233
Molecular Weight 581.85

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

DMSO(mg / mL) Max Solubility 100
DMSO(mM) Max Solubility 171.8656011
Water(mg / mL) Max Solubility <1
Molecular Weight 581.900 g/mol
XLogP3 9.600
Hydrogen Bond Donor Count 3
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 23
Exact Mass 581.365 Da
Monoisotopic Mass 581.365 Da
Topological Polar Surface Area 112.000 Ų
Heavy Atom Count 41
Formal Charge 0
Complexity 693.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 1
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Solution Calculators

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