{"ymdb_id":"YMDB01101","created_at":"2011-07-24T18:56:23.000Z","updated_at":"2016-09-08T18:36:16.000Z","name":"4-Hydroxysphinganine","cas":"554-62-1","state":"Solid","melting_point":"102-103 oC","description":"Phytosphingosine (4-hydroxysphinganine) is an intermediate in sphingolipid metabolism pathway. Sphingolipids are essential components of the plasma membrane in all eukaryotic cells. S. cerevisiae cells make three complex sphingolipids: inositol-phosphoceramide (IPC), mannose-inositol-phosphoceramide (MIPC), and mannosyl-diinositol-phosphorylceramide (M(IP)2C). Sphingolipid long chain bases (LCBs) - dihydrosphingosine (DHS) and phytosphingosine (PHS) - are implicated as secondary messengers in vital signaling pathways. [Biocyc SPHINGOLIPID-SYN-PWY]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":null,"synthesis_reference":null,"chebi_id":"46961","hmdb_id":"HMDB04610","kegg_id":"C12144","pubchem_id":"122121","cs_id":null,"foodb_id":null,"wikipedia_link":null,"biocyc_id":"PHYTOSPINGOSINE","iupac":"(2S,3S,4R)-2-aminooctadecane-1,3,4-triol","traditional_iupac":"phytosphingosine","logp":"3.6976906383333326","pka":"14.815152200058375","alogps_solubility":"4.46e-02 g/l","alogps_logp":"3.96","alogps_logs":"-3.85","acceptor_count":"4","donor_count":"4","rotatable_bond_count":"16","polar_surface_area":"86.71","refractivity":"92.2909","polarizability":"41.04821545288787","formal_charge":"0","physiological_charge":"1","pka_strongest_basic":"8.908333300303687","pka_strongest_acidic":"13.447718983386185","bioavailability":"1","number_of_rings":"0","rule_of_five":"1","ghose_filter":"1","veber_rule":"0","mddr_like_rule":"0","synonyms":["(+)-D-ribo-Phytosphingosine","[2S-(2R*,3R*,4S*)]-2-amino-1,3,4-Octadecanetriol","4-D-hydroxy-Sphinganine","4-D-Hydroxysphinganine","4D-Hydroxysphinganine","C18-Phytosphingosine","Ceramide II","D-ribo-1,3,4-Trihydroxy-2-aminooctadecane","D-ribo-2-amino-1,3,4-Octadecanetriol","Kohlenstoff","N-Acyl-4-hydroxysphinganine","Phytoceramide","Phytosphingosine"],"pathways":[{"name":"Sphingolipid metabolism","kegg_map_id":"00600"},{"name":"Biosynthesis of unsaturated fatty acids","kegg_map_id":"01040"},{"name":"Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)","kegg_map_id":null},{"name":"Biosynthesis of unsaturated fatty acids (docosanoyl)","kegg_map_id":null},{"name":"Biosynthesis of unsaturated fatty acids (icosanoyl)","kegg_map_id":null},{"name":"Biosynthesis of unsaturated fatty acids (stearoyl)","kegg_map_id":null}],"growth_conditions":[],"references":[{"pubmed_id":19174513,"citation":"Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). \"Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry.\" Proc Natl Acad Sci U S A 106:2136-2141."}],"proteins":[]}