MetaCyc Compound: L-threo-sphinganine

Synonyms: L-threo-dihydrosphingosine, threo-L-sphinganine, L-threo-DHS, L-threo-dihydrosphingosine (C18), L-threo-sphinganine (C18), safingol

Superclasses: an alcoholan amino alcohola sphingoid basea sphinganine

There are two different stereoisomers of dihydrosphinganine. The D-erythro isomer is the biologically relevant form [Chao11], but this L-threo-sphinganine isomer may have anticancer properties [Morales07].

Chemical Formula: C18H40NO2

Molecular Weight: 302.52 Daltons

Monoisotopic Molecular Weight: 302.3059045334 Daltons

L-<i>threo</i>-sphinganine compound structure


InChI: 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/p+1/t17-,18-/m0/s1


Unification Links: ChemSpider:2319840, PubChem:90658247

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 352.09277Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

ceramide degradation :
a sphingoid base + ATP → a sphingoid 1-phosphate + ADP + H+

Reactions known to produce the compound:

ceramide degradation :
a ceramide + H2O → a sphingoid base + a fatty acid

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol

In Reactions of unknown directionality:

Not in pathways:
L-threo-sphinganine + NADP+ = 3-dehydrosphinganine + NADPH + H+

Not in pathways:
a sphinganine + NAD+ = 3-dehydrosphinganine + NADH + H+

Not in pathways:
an acyl-CoA + a sphingoid base = a ceramide + coenzyme A + H+

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes activated by L-threo-sphinganine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]

This compound has been characterized as an alternative substrate of the following enzymes: sphingosine kinase

Created 23-Sep-2011 by Dreher KA, PMN


Chao11: Chao DY, Gable K, Chen M, Baxter I, Dietrich CR, Cahoon EB, Guerinot ML, Lahner B, Lu S, Markham JE, Morrissey J, Han G, Gupta SD, Harmon JM, Jaworski JG, Dunn TM, Salt DE (2011). "Sphingolipids in the root play an important role in regulating the leaf ionome in Arabidopsis thaliana." Plant Cell 23(3);1061-81. PMID: 21421810

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Morales07: Morales PR, Dillehay DL, Moody SJ, Pallas DC, Pruett S, Allgood JC, Symolon H, Merrill AH (2007). "Safingol toxicology after oral administration to TRAMP mice: demonstration of safingol uptake and metabolism by N-acylation and N-methylation." Drug Chem Toxicol 30(3);197-216. PMID: 17613006

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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