≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
DI-591 is a potent, high-affinity and cell-permeable inhibitor of the DCN1-UBC12 interaction. DI-591 binds to DCN1 and DCN2 with K i values of 12 nM and 10.4 nM, respectively and has no appreciable binding to DCN3, DCN4, and DCN5 proteins. DI-591 selectively inhibits neddylation of cullin 3 but has no or minimal effect on neddylation of other cullin family members
In Vitro
DI-591 (Compound 44) binds to DCN1 and DCN2 with K i values of 12 nM and 10.4 nM, respectively and has no appreciable binding to DCN3, DCN4, and DCN5 proteins. Hence, DI-591 displays a very-high binding affinity to recombinant human DCN1 and DCN2 proteins and >1000-fold selectivity over recombinant human DCN3-5 proteins. DI-591 (Compound 44; 0-10 μM; 1 hour; KYSE70 cells) binds to both cellular DCN1 and DCN2 proteins and disrupts the association of cellular DCN1 and UBC12 proteins. DI-591 (Compound 44; 10 μM; 24 hours; THLE2 cells) treatment robustly increases the mRNA levels of NQO1 and HO1, leading to upregulation of HO1 protein in the cells. Significantly, DI-591 has no effect on the mRNA level of NRF2. The selective inhibition of neddylation of cullin 3 by DI-591 leads to accumulation NRF2 protein and its transcriptional activation. Knockdown experiments indicate that DCN1, but not DCN2, plays a key role in regulation of neddylation of cullin 3 but not of other cullins. DI-591 is an excellent probe compound to investigate the role of the cullin 3 CRL (Cullin-RING E3 ubiquitin ligase) in biological processes and human diseases. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: KYSE70 cells Concentration: 0 μM, 1 μM, 3 Μm or 10 μM Incubation Time: 1 hour Result: Potently bound to cellular DCN1 and DCN2 proteins. Enhanced the stability of DCN1 and DCN2 protein in a dose-dependent manner. RT-PCRCell Line: THLE2 cells Concentration: 10 μM Incubation Time: 24 hours Result: Robustly increases the mRNA levels of NQO1 and HO1.
Form:Solid
IC50& Target:DCN1-UBC12
| Kanonisches Lächeln | CCC(=O)NC(CC1=NC2=C(S1)C=C(C=C2)C(C)C)C(=O)NC(CNC(=O)CCN3CCOCC3)C4CCCCC4 |
|---|---|
| IUPAC Name | (2S)-N-[(1S)-1-cyclohexyl-2-(3-morpholin-4-ylpropanoylamino)ethyl]-2-(propanoylamino)-3-(6-propan-2-yl-1,3-benzothiazol-2-yl)propanamide |
| InChIKey | CNJKDQGPBAWNRY-IZZNHLLZSA-N |
| INCHI | 1S/C31H47N5O4S/c1-4-28(37)33-25(19-30-34-24-11-10-23(21(2)3)18-27(24)41-30)31(39)35-26(22-8-6-5-7-9-22)20-32-29(38)12-13-36-14-16-40-17-15-36/h10-11,18,21-22,25-26H,4-9,12-17,19-20H2,1-3H3,(H,32,38)(H,33,37)(H,35,39)/t25-,26+/m0/s1 |
| Isomere SMILES | CCC(=O)N[C@@H](CC1=NC2=C(S1)C=C(C=C2)C(C)C)C(=O)N[C@H](CNC(=O)CCN3CCOCC3)C4CCCCC4 |
| PubChem CID | 131750123 |
| MeSH-Eintrag | (S)-N-((S)-1-cyclohexyl-2-(3-morpholinopropanamido)ethyl)-3-(6-isopropylbenzo(d)thiazol-3 2-yl)-2-propionamidopropanamide;DI-591 |
| Molekulargewicht | 585.80 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Klasse | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | N-acyl-alpha amino acids and derivatives |
| Alternative Parents | Alpha amino acid amides Beta amino acids and derivatives Benzothiazoles Morpholines Fatty amides Benzenoids Thiazoles Heteroaromatic compounds Trialkylamines Secondary carboxylic acid amides Oxacyclic compounds Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Beta amino acid or derivatives - 1,3-benzothiazole - Fatty acyl - Benzenoid - Oxazinane - Morpholine - Fatty amide - Heteroaromatic compound - Thiazole - Azole - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Oxacycle - Azacycle - Organoheterocyclic compound - Ether - Dialkyl ether - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Aromatic heteropolycyclic compound |
| Beschreibung | This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. |
| External Descriptors | Not available |
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Löslichkeit | DMSO : 12.5 mg/mL (21.34 mM; ultrasonic and warming and heat to 60°C) |
|---|---|
| Molekulargewicht | 585.800 g/mol |
| XLogP3 | 4.300 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 13 |
| Exact Mass | 585.335 Da |
| Monoisotopic Mass | 585.335 Da |
| Topological Polar Surface Area | 141.000 Ų |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Complexity | 848.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| 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 |
