L-threo-dihydrosphingosine (d18:0) - ≥98% , CAS No.15639-50-6

CAS: 15639-50-6 Cat. No.: L130602 Molecular Weight: 301.51

GRADE & PURITY ≥98%

Synonyms

L-threo-Dihydrosphingosine | SMP2_000060 | 1, 2-amino- (2S,3S) | 2S,3S-Dihydrosphingosine | SAFINGOL [USAN] | SPC-100270 | Tox21_111227 | 2S-aminooctadecane-1,3R-diol | OWA98U788S | SL-205 | DB11924 | NCGC00093867-01 | Tox21_111227_1 | Bio1_000520 | rel-(

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A dual inhibitor of PKC and SPHK

Application:

L-threo-Dihydrosphingosine is a lyso-sphingolipid protein kinase C inhibitor. It suppresses the growth of human oral squamous cell carcinoma (SCC)

Specifications

Synonyms

L-threo-Dihydrosphingosine | SMP2_000060 | 1, 2-amino- (2S, 3S) | 2S, 3S-Dihydrosphingosine | SAFINGOL [USAN] | SPC-100270 | Tox21_111227 | 2S-aminooctadecane-1, 3R-diol | OWA98U788S | SL-205 | DB11924 | NCGC00093867-01 | Tox21_111227_1 | Bio1_000520 | rel-(

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Cell-permeable, reversible lyso-sphingolipid protein kinase C (PKC) inhibitor (IC 50 = 40 µM). Anticancer agent. Potentiates effect of D oxorubicin (DOX) in tumor-bearing animals and cytotoxicity of Mitomycin C in cancer cells.

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.

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. 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(C(CO)N)O
• IUPAC Name: (2S,3S)-2-aminooctadecane-1,3-diol
• InChIKey: OTKJDMGTUTTYMP-ROUUACIJSA-N
• INCHI: 1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCC[C@@H]([C@H](CO)N)O
• WGK Germany: 3
• Molecular Weight: 301.51
• Reaxy-Rn: 1772584
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1772584&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,2-aminoalcohols

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines
• Direct Parent: 1,2-aminoalcohols
• Alternative Parents: Secondary alcohols Primary alcohols Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Secondary alcohol - 1,2-aminoalcohol - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
• External Descriptors: Sphingoid base analogs

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)

MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

Discover Target: MTOR

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

SPHK1 Tchem Sphingosine kinase 1 (1990 Activities)

Discover Target: SPHK1

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

Associated Targets(non-human)

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

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 chloroform, water (partly miscible), DMSO (~2 mg/ml), DMF (~10 mg/ml), ethanol, and methanol.
• Flash Point(°F): >230 °F
• Flash Point(°C): >110 °C
• Boil Point(°C): >300° C
• Melt Point(°C): 106.8-108.7° C
• Molecular Weight: 301.500 g/mol
• XLogP3: 5.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 301.298 Da
• Monoisotopic Mass: 301.298 Da
• Topological Polar Surface Area: 66.500 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 200.000
• 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