Description
Key facts
CAS number:35891-70-4,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:401.5 Da,
Molecular formula:C21H39NO6,
PubChem:6438394,
Nature:Synthetic,
Solubility:Soluble in DMSO to 50 mM (with heating)Soluble in NaOH to 10 mM,
Biochemical name:Myriocin,
Biological description:Highly potent serine palmitoyltransferase inhibitor (Ki = 0.28 nM). Shows 10 times the immunosuppressant potency of cyclosporine (ab141923, ab143599). Depletes cellular sphingolipids and induces apoptosis. Inhibits proliferation (IC50 = 15 nM, CTLL-1). Inhibits sphingosine biosynthesis in vivo. Orally active.,
Canonical smiles:CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O,
Isomeric smiles:CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@@](CO)(C(=O)O)N)O)O,
InChi:InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1,
InChiKey:ZZIKIHCNFWXKDY-GNTQXERDSA-N,
IUPAC Name:(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-+4°C, Appropriate long-term storage conditions-+4°C, Storage information-The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
Serine palmitoyltransferase (SPT) sometimes referred to as SPTLC is an enzyme that plays an important role in the initial step of sphingolipid biosynthesis. It catalyzes the condensation of serine and palmitoyl-CoA yielding 3-ketodihydrosphingosine. This enzyme complex consists of subunits SPTLC1 SPTLC2 and sometimes SPTLC3 with a molecular weight around 53 kDa for SPTLC1. Expression of SPT is seen in various tissues including the liver and nervous system supporting its critical functions across the body.
Biological function summary
Serine palmitoyltransferase is involved in sphingolipid metabolism contributing to the formation of essential cellular components. It acts as a part of a larger enzyme complex responsible for generating sphingolipid precursors. These sphingolipids play a role in membrane structure and cell signaling affecting processes like cell growth and apoptosis. The enzyme therefore influences fundamental cellular phenomena demonstrating its widespread relevance in biochemistry and cell biology.
Pathways
Serine palmitoyltransferase is vital in the de novo sphingolipid biosynthesis pathway where it initiates the creation of long-chain bases the core of most sphingolipids. It also links to the lipid metabolism pathway sharing interactions with proteins like ceramide synthase. By producing the starting materials for sphingolipids SPT integrates deeply into lipid regulation and signaling pathways affecting how cells communicate and respond to their environment.
Serine palmitoyltransferase has connections to disorders like hereditary sensory and autonomic neuropathy type I (HSAN1) and metabolic syndromes. Mutations in the SPTLC1 subunit can lead to HSAN1 illustrating its direct involvement in nerve function and health. Additionally altered sphingolipid metabolism implicates SPT in metabolic syndromes where it interacts with proteins like ceramide influencing insulin resistance and lipid homeostasis. These connections emphasize the enzyme's significance in disease development and potential therapeutic targeting.
