1.0 2016-09-30 23:11:44 UTC 2020-05-11 20:32:50 UTC BMDB0004873 BMDB04873 Lactosylceramide (d18:1/26:1(17Z)) (17Z)-N-[(2S,3R,4E)-1-{[(2R,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexacos-17-enimidate C56H105NO13 1000.45 999.758592445 (17Z)-N-[(2S,3R,4E)-1-{[(2R,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexacos-17-enimidic acid (17Z)-N-[(2S,3R,4E)-1-{[(2R,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexacos-17-enimidic acid [H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@]1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC InChI=1S/C56H105NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-48(61)57-44(45(60)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2)43-67-55-53(66)51(64)54(47(42-59)69-55)70-56-52(65)50(63)49(62)46(41-58)68-56/h17-18,37,39,44-47,49-56,58-60,62-66H,3-16,19-36,38,40-43H2,1-2H3,(H,57,61)/b18-17-,39-37+/t44-,45+,46+,47+,49-,50-,51+,52+,53-,54+,55+,56-/m0/s1 ZUFRMROYCSRBIP-URQQICDRSA-N belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Organic compounds Lipids and lipid-like molecules Sphingolipids Glycosphingolipids Glycosyl-N-acylsphingosines Acetals Alkyl glycosides Carbonyl compounds Disaccharides Fatty acyl glycosides of mono- and disaccharides Hydrocarbon derivatives N-acyl amines O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Alcohol Aliphatic heteromonocyclic compound Alkyl glycoside Carbonyl group Carboxamide group Carboxylic acid derivative Disaccharide Fatty acyl Fatty acyl glycoside Fatty acyl glycoside of mono- or disaccharide Fatty amide Glycosyl compound Glycosyl-n-acylsphingosine Hydrocarbon derivative N-acyl-amine O-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Aliphatic heteromonocyclic compounds Solid logp 7.68 ALOGPS logs -5.56 ALOGPS logp 12.23 ChemAxon pka_strongest_acidic 5.81 ChemAxon pka_strongest_basic 2.6 ChemAxon iupac (17Z)-N-[(2S,3R,4E)-1-{[(2R,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexacos-17-enimidic acid ChemAxon average_mass 1000.45 ChemAxon mono_mass 999.758592445 ChemAxon smiles [H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@]1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC ChemAxon formula C56H105NO13 ChemAxon inchi InChI=1S/C56H105NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-48(61)57-44(45(60)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2)43-67-55-53(66)51(64)54(47(42-59)69-55)70-56-52(65)50(63)49(62)46(41-58)68-56/h17-18,37,39,44-47,49-56,58-60,62-66H,3-16,19-36,38,40-43H2,1-2H3,(H,57,61)/b18-17-,39-37+/t44-,45+,46+,47+,49-,50-,51+,52+,53-,54+,55+,56-/m0/s1 ChemAxon inchikey ZUFRMROYCSRBIP-URQQICDRSA-N ChemAxon polar_surface_area 231.35 ChemAxon refractivity 278.25 ChemAxon polarizability 122.61 ChemAxon rotatable_bond_count 45 ChemAxon acceptor_count 14 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 1221619 Specdb::MsMs 1221620 Specdb::MsMs 1221621 Specdb::MsMs 1337284 Specdb::MsMs 1337285 Specdb::MsMs 1337286 Adrenal Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 57504236 Nicolaou, K. C.; Caulfield, T.; Kataoka, H.; Kumazawa, T. A practical and enantioselective synthesis of glycosphingolipids and related compounds. Total synthesis of globotriaosylceramide (Gb3). Journal of the American Chemical Society (1988), 110(23), 791