DL-threo-PPMP (hydrochloride) - Moligand™, ≥98% , CAS No.139974-41-7

CAS: 139974-41-7 Cat. No.: D276171 Molecular Weight: 511.19

GRADE & PURITY Moligand™, ≥98%

Synonyms

DL-threo-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol | rel-N-[(1R,2R)-2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-hexadecanamide, monohydrochloride

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

DL-threo-PPMP is a ceramide analog and an inhibitor of glucosylceramide synthase. It inhibits glucosylceramide synthase by 70, 41, and 62% in MDCK cell homogenates, mouse liver microsomes, and mouse brain homogenates, respectively, when used at a concentration of 20 µM. DL-threo-PPMP also inhibits sphingomyelin synthase activity in erythrocytes infected with P. falciparum and inhibits late ring-stage P. falciparum growth (IC50 = 0.85 µM). It reduces Akt and ribosomal protein S6 phosphorylation in HEK293 cells and increases autophagy flux in primary mouse neurons.

Specifications

Synonyms

DL-threo-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol | rel-N-[(1R, 2R)-2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-hexadecanamide, monohydrochloride

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Glucosylceramide synthase inhibitor. Useful in ER anterograde trafficking studies. Anticancer and antimalarial (IC 50 = 0.85 µM) agent. Active in vitro.s

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™

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. 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: CCCCCCCCCCCCCCCC(=O)NC(CN1CCOCC1)C(C2=CC=CC=C2)O.Cl
• IUPAC Name: N-[(1R,2R)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]hexadecanamide;hydrochloride
• InChIKey: ORVAUBQYJOFWFY-ZHESDOBJSA-N
• INCHI: 1S/C29H50N2O3.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-28(32)30-27(25-31-21-23-34-24-22-31)29(33)26-18-15-14-16-19-26;/h14-16,18-19,27,29,33H,2-13,17,20-25H2,1H3,(H,30,32);1H/t27-,29-;/m1./s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H](CN1CCOCC1)[C@@H](C2=CC=CC=C2)O.Cl
• Alternate CAS: 149022-18-4（free base）
• Molecular Weight: 511.19
• Reaxy-Rn: 11736004
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11736004&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aralkylamines
• Alternative Parents: N-acyl amines Morpholines Benzene and substituted derivatives 1,3-aminoalcohols Trialkylamines Secondary carboxylic acid amides Secondary alcohols Amino acids and derivatives Oxacyclic compounds Azacyclic compounds Dialkyl ethers Hydrochlorides Organic oxides Carbonyl compounds Aromatic alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aralkylamine - Monocyclic benzene moiety - Fatty amide - Morpholine - N-acyl-amine - Oxazinane - Fatty acyl - Benzenoid - 1,3-aminoalcohol - Amino acid or derivatives - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Tertiary amine - Tertiary aliphatic amine - Azacycle - Oxacycle - Ether - Dialkyl ether - Carboxylic acid derivative - Organoheterocyclic compound - Hydrochloride - Organooxygen compound - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organic oxide - Carbonyl group - Aromatic alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
• 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)

UGCG Tclin Ceramide glucosyltransferase (308 Activities)

Discover Target: UGCG

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 10 mM
• Sensitivity: Moisture sensitive.
• Molecular Weight: 474.700 g/mol
• XLogP3: 7.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 19
• Exact Mass: 474.382 Da
• Monoisotopic Mass: 474.382 Da
• Topological Polar Surface Area: 61.800 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 490.000
• 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