| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2022-03-07 02:49:22 UTC |
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| HMDB ID | HMDB0004866 |
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| Secondary Accession Numbers | - HMDB0000173
- HMDB00173
- HMDB04866
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| Metabolite Identification |
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| Common Name | LacCer(d18:1/12:0) |
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| Description | LacCer(d18:1/12:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted. from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6 (EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). Moreover, lactosylceramide (D18:1/12:0) is found to be associated with abetalipoproteinemia and hypobetalipoproteinemia, which are inborn errors of metabolism. |
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| Structure | [H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC InChI=1S/C42H79NO13/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-31(46)30(43-34(47)26-24-22-20-17-12-10-8-6-4-2)29-53-41-39(52)37(50)40(33(28-45)55-41)56-42-38(51)36(49)35(48)32(27-44)54-42/h23,25,30-33,35-42,44-46,48-52H,3-22,24,26-29H2,1-2H3,(H,43,47)/b25-23+/t30-,31+,32+,33+,35-,36-,37+,38+,39+,40+,41+,42-/m0/s1 |
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| Synonyms | | Value | Source |
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| LacCer d18:1/12:0 | HMDB | | LacCer(d18:1/12:0) | HMDB | | Lactosylceramide (d18:1,C12:0) | HMDB | | Lactosylceramide (d18:1/12:0) | HMDB | | Lactosylceramide(d18:1/12:0) | HMDB | | N-(Dodecanoyl)-1-beta-lactosyl-sphing-4-enine | HMDB | | N-(Dodecanoyl)-1-β-lactosyl-sphing-4-enine | HMDB |
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| Chemical Formula | C42H79NO13 |
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| Average Molecular Weight | 806.088 |
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| Monoisotopic Molecular Weight | 805.555141608 |
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| IUPAC Name | N-[(2S,3R,4E)-1-{[(2R,3R,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]dodecanamide |
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| Traditional Name | N-[(2S,3R,4E)-1-{[(2R,3R,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]dodecanamide |
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| CAS Registry Number | 474943-80-1 |
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| SMILES | [H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C42H79NO13/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-31(46)30(43-34(47)26-24-22-20-17-12-10-8-6-4-2)29-53-41-39(52)37(50)40(33(28-45)55-41)56-42-38(51)36(49)35(48)32(27-44)54-42/h23,25,30-33,35-42,44-46,48-52H,3-22,24,26-29H2,1-2H3,(H,43,47)/b25-23+/t30-,31+,32+,33+,35-,36-,37+,38+,39+,40+,41+,42-/m0/s1 |
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| InChI Key | KNWHKVBHCLQVFX-CZUYTOTJSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Not Available | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0 | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross Sections| Predictor | Adduct Type | CCS Value (Å2) | Reference |
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| DeepCCS | [M+H]+ | 277.569 | 30932474 | | DeepCCS | [M-H]- | 275.755 | 30932474 | | DeepCCS | [M-2H]- | 309.791 | 30932474 | | DeepCCS | [M+Na]+ | 283.808 | 30932474 |
Predicted Kovats Retention IndicesDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| LacCer(d18:1/12:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5727.7 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5340.5 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #1 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8304.4 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5707.2 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5344.7 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #2 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8305.4 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5715.9 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5352.9 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #3 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8176.1 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #4 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5702.7 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #4 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5341.7 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #4 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8156.5 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #5 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5684.2 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #5 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5346.8 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #5 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8207.1 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #6 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[Si](C)(C)C)[C@H]1O)NC(=O)CCCCCCCCCCC | 5711.3 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #6 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[Si](C)(C)C)[C@H]1O)NC(=O)CCCCCCCCCCC | 5316.0 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #6 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[Si](C)(C)C)[C@H]1O)NC(=O)CCCCCCCCCCC | 8200.2 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #7 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[Si](C)(C)C)NC(=O)CCCCCCCCCCC | 5719.8 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #7 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[Si](C)(C)C)NC(=O)CCCCCCCCCCC | 5327.4 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #7 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[Si](C)(C)C)NC(=O)CCCCCCCCCCC | 8192.0 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #8 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5745.2 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #8 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 5248.5 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #8 | CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC | 8179.7 | Standard polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #9 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C | 5655.3 | Semi standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #9 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C | 5317.0 | Standard non polar | 33892256 | | LacCer(d18:1/12:0),1TMS,isomer #9 | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C | 8303.9 | Standard polar | 33892256 |
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| General References | - Takizawa M, Nomura T, Wakisaka E, Yoshizuka N, Aoki J, Arai H, Inoue K, Hattori M, Matsuo N: cDNA cloning and expression of human lactosylceramide synthase. Biochim Biophys Acta. 1999 May 18;1438(2):301-4. [PubMed:10320813 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. [PubMed:9106497 ]
- Choudhury A, Dominguez M, Puri V, Sharma DK, Narita K, Wheatley CL, Marks DL, Pagano RE: Rab proteins mediate Golgi transport of caveola-internalized glycosphingolipids and correct lipid trafficking in Niemann-Pick C cells. J Clin Invest. 2002 Jun;109(12):1541-50. [PubMed:12070301 ]
- Sala G, Dupre T, Seta N, Codogno P, Ghidoni R: Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts. Pediatr Res. 2002 Nov;52(5):645-51. [PubMed:12409508 ]
- Furukawa K, Takamiya K, Furukawa K: Beta1,4-N-acetylgalactosaminyltransferase--GM2/GD2 synthase: a key enzyme to control the synthesis of brain-enriched complex gangliosides. Biochim Biophys Acta. 2002 Dec 19;1573(3):356-62. [PubMed:12417418 ]
- Komagome R, Sawa H, Suzuki T, Suzuki Y, Tanaka S, Atwood WJ, Nagashima K: Oligosaccharides as receptors for JC virus. J Virol. 2002 Dec;76(24):12992-3000. [PubMed:12438625 ]
- Prinetti A, Basso L, Appierto V, Villani MG, Valsecchi M, Loberto N, Prioni S, Chigorno V, Cavadini E, Formelli F, Sonnino S: Altered sphingolipid metabolism in N-(4-hydroxyphenyl)-retinamide-resistant A2780 human ovarian carcinoma cells. J Biol Chem. 2003 Feb 21;278(8):5574-83. Epub 2002 Dec 16. [PubMed:12486134 ]
- Moore RM, Silver RJ, Moore JJ: Physiological apoptotic agents have different effects upon human amnion epithelial and mesenchymal cells. Placenta. 2003 Feb-Mar;24(2-3):173-80. [PubMed:12566244 ]
- Hulkova H, Ledvinova J, Asfaw B, Koubek K, Kopriva K, Elleder M: Lactosylceramide in lysosomal storage disorders: a comparative immunohistochemical and biochemical study. Virchows Arch. 2005 Jul;447(1):31-44. Epub 2005 May 26. [PubMed:15918012 ]
- Sharma DK, Brown JC, Cheng Z, Holicky EL, Marks DL, Pagano RE: The glycosphingolipid, lactosylceramide, regulates beta1-integrin clustering and endocytosis. Cancer Res. 2005 Sep 15;65(18):8233-41. [PubMed:16166299 ]
- Stevens CR, Oberholzer VG, Walker-Smith JA, Phillips AD: Lactosylceramide in inflammatory bowel disease: a biochemical study. Gut. 1988 May;29(5):580-7. [PubMed:3396945 ]
- Tanaka H, Suzuki K: Lactosylceramidase assays for diagnosis of globoid cell leukodystrophy and GM1-gangliosidosis. Clin Chim Acta. 1977 Mar 1;75(2):267-74. [PubMed:403037 ]
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