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MetaCyc Compound Class: a sphingoid base

Synonyms: a sphingolipid long chain base, LCB

Superclasses: an alcohol an amino alcohol

Summary:
Sphingoids (sphingoid bases, or long chain bases) are building blocks of sphingolipids. They are amino alcohols, composed predominantly of 18 carbon atoms. They are characterized by the presence of a hydroxyl group at C1 (and often also at C3), and an amine group at C2. The commonly known sphingoids include sphingosine, sphinganine (dihydrosphingosine), and phytosphingosine (4-hydroxysphinganine).

a sphingoid base compound structure

Child Classes: a 4-hydroxy-8-sphingenine (2) , a sphinganine (2) , a sphingoid 1-phosphate (3)

Instances:
(4E,8E)-sphinga-4,8-dienine ,
(4E,8E,10E)-sphinga-4,8-trienine ,
3-dehydrosphinganine ,
3-dehydrosphinganine (C20) ,
9-methyl-(4E,8E)-sphinga-4,8-dienine ,
O-galactosylsphingosine ,
O-glucosyl-sphingosine ,
phytosphingosine ,
sphinganine (C20) ,
sphingosine ,
sphingosylphosphorylcholine

Citations: [Pata10]

SMILES: C(O)([R])C([N+])CO

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 , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
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 → β-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
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

In Reactions of unknown directionality:

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+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucopyranose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
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 a sphingoid base, sorted by the type of activation, are:

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

Credits:
Created 08-Apr-2010 by Zhang P , TAIR


References

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

Pata10: Pata MO, Hannun YA, Ng CK (2010). "Plant sphingolipids: decoding the enigma of the Sphinx." New Phytol 185(3);611-30. PMID: 20028469

Thudichum84: Thudichum, J. L. W. (1884). "A Treatise on the Chemical Constitution of Brain." Bailliere, Tindall, and Cox, London.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Thu Sep 3, 2015, biocyc13.