1.0 2016-09-30 23:11:43 UTC 2020-05-11 20:32:49 UTC BMDB0004872 BMDB04872 Lactosylceramide (d18:1/24:1(15Z)) (15Z)-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]tetracos-15-enimidate C54H101NO13 972.396 971.727292316 (15Z)-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]tetracos-15-enimidic acid (15Z)-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]tetracos-15-enimidic acid [H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(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/C54H101NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-46(59)55-42(43(58)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)41-65-53-51(64)49(62)52(45(40-57)67-53)68-54-50(63)48(61)47(60)44(39-56)66-54/h17-18,35,37,42-45,47-54,56-58,60-64H,3-16,19-34,36,38-41H2,1-2H3,(H,55,59)/b18-17-,37-35+/t42-,43+,44+,45+,47-,48-,49+,50+,51-,52+,53+,54-/m0/s1 MKOKWBRPIBQYJJ-PSSITMGYSA-N Solid logp 7.36 ALOGPS logs -5.43 ALOGPS logp 11.34 ChemAxon pka_strongest_acidic 5.81 ChemAxon pka_strongest_basic 2.6 ChemAxon iupac (15Z)-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]tetracos-15-enimidic acid ChemAxon average_mass 972.396 ChemAxon mono_mass 971.727292316 ChemAxon smiles [H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(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 C54H101NO13 ChemAxon inchi InChI=1S/C54H101NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-46(59)55-42(43(58)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)41-65-53-51(64)49(62)52(45(40-57)67-53)68-54-50(63)48(61)47(60)44(39-56)66-54/h17-18,35,37,42-45,47-54,56-58,60-64H,3-16,19-34,36,38-41H2,1-2H3,(H,55,59)/b18-17-,37-35+/t42-,43+,44+,45+,47-,48-,49+,50+,51-,52+,53+,54-/m0/s1 ChemAxon inchikey MKOKWBRPIBQYJJ-PSSITMGYSA-N ChemAxon polar_surface_area 231.35 ChemAxon refractivity 269.05 ChemAxon polarizability 118.15 ChemAxon rotatable_bond_count 43 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 1243378 Specdb::MsMs 1243379 Specdb::MsMs 1243380 Specdb::MsMs 1358746 Specdb::MsMs 1358747 Specdb::MsMs 1358748 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 138521154 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