DMAPT - Moligand™, ≥98% , CAS No.870677-05-7

CAS: 870677-05-7 Cat. No.: D275187 Molecular Weight: 293.41 EC Number: 112-690-1

GRADE & PURITY Moligand™, ≥98%

Synonyms

(S)-DMAPT | HY-16172 | DMAPT | (1S,2R,4R,7Z,11S,12S)-12-[(dimethylamino)methyl]-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0?,?]tetradec-7-en-13-one | NSC-734325 | LC-1 | (1S,2R,4R,7Z,11S,12S)-12-[(dimethylamino)methyl]-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

DMAPT (Dimethylamino Parthenolide) is an NF-κB inhibitor and a Parthenolide (PTL) analogue with an LD50 value of 1.7 μM for primary acute myeloid leukemia cells. It has potential anti-tumor and anti-metastatic effects.

Specifications

Synonyms

(S)-DMAPT | HY-16172 | DMAPT | (1S, 2R, 4R, 7Z, 11S, 12S)-12-[(dimethylamino)methyl]-4, 8-dimethyl-3, 14-dioxatricyclo[9.3.0.0?, ?]tetradec-7-en-13-one | NSC-734325 | LC-1 | (1S, 2R, 4R, 7Z, 11S, 12S)-12-[(dimethylamino)methyl]-4, 8-dimethyl-3, 14-dioxatricyclo[9.3.0.02

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

NF-κB inhibitor. Reduces NF-κB DNA binding. Shows antiproliferative effects (IC 50 = 5-10 μM). Parthenolide analog. Epigenetic modulator, functions NFκB-dependently and independently. Generates ROS and shows antitumor effects in vivo.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CCCC2(C(O2)C3C(CC1)C(C(=O)O3)CN(C)C)C
• IUPAC Name: (1S,2R,4R,7Z,11S,12S)-12-[(dimethylamino)methyl]-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
• InChIKey: UJNSFDHVIBGEJZ-CMRIBGNTSA-N
• INCHI: 1S/C17H27NO3/c1-11-6-5-9-17(2)15(21-17)14-12(8-7-11)13(10-18(3)4)16(19)20-14/h6,12-15H,5,7-10H2,1-4H3/b11-6-/t12-,13+,14-,15+,17+/m0/s1
• Isomeric SMILES: C/C/1=C/CC[C@@]2([C@H](O2)[C@@H]3[C@@H](CC1)[C@H](C(=O)O3)CN(C)C)C
• Molecular Weight: 293.41
• Reaxy-Rn: 31787085
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31787085&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Terpene lactones
• Alternative Parents: Germacrane sesquiterpenoids Fatty acid esters Gamma butyrolactones Tetrahydrofurans Trialkylamines Carboxylic acid esters Amino acids and derivatives Oxacyclic compounds Monocarboxylic acids and derivatives Epoxides Dialkyl ethers Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Terpene lactone - Farsesane sesquiterpenoid - Sesquiterpenoid - Germacrane sesquiterpenoid - Fatty acid ester - Fatty acyl - Gamma butyrolactone - Tetrahydrofuran - Tertiary aliphatic amine - Tertiary amine - Lactone - Carboxylic acid ester - Amino acid or derivatives - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Amine - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
• 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

Chemical and Physical Properties

• Solubility: H2O: insoluble ；DMSO: 100 mg/mL (340.83 mM),
• Molecular Weight: 293.400 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 293.199 Da
• Monoisotopic Mass: 293.199 Da
• Topological Polar Surface Area: 42.100 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 459.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1