Thiomyristoyl - ≥98% , CAS No.1429749-41-6

CAS: 1429749-41-6 Cat. No.: T413952 Molecular Weight: 581.85 PubChem CID: 126843233

GRADE & PURITY ≥98%

Synonyms

TM | Carbamic acid,N-​[(1S)​-​1-​[(phenylamino)​carbonyl]​-​5-​[(1-​thioxotetradecyl)​amino]​pentyl]​-​,phenylmethyl ester | (S)-benzyl (1-oxo-1-(phenylamino)-6-tetradecanethioamidohexan-2-yl)carbamate

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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 

Specifications

Synonyms

TM | Carbamic acid, N-​[(1S)​-​1-​[(phenylamino)​carbonyl]​-​5-​[(1-​thioxotetradecyl)​amino]​pentyl]​-​, phenylmethyl ester | (S)-benzyl (1-oxo-1-(phenylamino)-6-tetradecanethioamidohexan-2-yl)carbamate

Specifications & Purity

≥98%

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

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• ALogP: 9.441
• HBD Count: 3
• Rotatable Bond: 24

Names and Identifiers

• Pubchem Sid: 504773021
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773021
• Canonical Smiles: CCCCCCCCCCCCCC(=S)NCCCCC(C(=O)NC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
• IUPAC Name: benzyl N-[(2S)-1-anilino-1-oxo-6-(tetradecanethioylamino)hexan-2-yl]carbamate
• InChIKey: CJQGLLUJIVNREL-HKBQPEDESA-N
• 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
• 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

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acid amides

• 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SIRT2 Tchem NAD-dependent protein deacetylase sirtuin-2 (6 Activities)

Discover Target: SIRT2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

BXPC-3 (2997 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDA-MB-468 (9477 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HCT-116 (91556 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HeLa (62764 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDA-MB-231 (73002 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H23 (49055 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SIRT3 Tchem NAD-dependent deacetylase sirtuin 3 (1285 Activities)

Discover Target: SIRT3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)

Discover Target: SIRT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SW948 (147 Activities)

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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)

Discover Target: SIRT6

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)

Discover Target: SIRT5

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)

Discover Target: SIRT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

N2a (708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 100 mg/mL (171.86 mM); Ethanol: 100 mg/mL warmed with 50ºC Water: bath (171.86 mM); Water: Insoluble
• 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