Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-05-25 18:09:15 UTC |
---|
Update Date | 2016-11-09 01:17:20 UTC |
---|
Accession Number | CHEM021654 |
---|
Identification |
---|
Common Name | Trihexosylceramide (d18:1/12:0) |
---|
Class | Small Molecule |
---|
Description | |
---|
Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
|
---|
Contaminant Type | Not Available |
---|
Chemical Structure | |
---|
Synonyms | Value | Source |
---|
N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanimidate | HMDB | Ceramide trihexoside | HMDB | D-Galactosyl-1,4-D-galactosyl-1,4-D-glucosylceramide | HMDB | delta-Galactosyl-1,4-delta-galactosyl-1,4-delta-glucosylceramide | HMDB | Fabry glycolipid | HMDB | Gal-alpha1->4gal-beta1->4GLC-beta1->1'cer | HMDB | Gal-alpha1->4laccer | HMDB | Ganglioside GL3 | HMDB | Gb3 | HMDB | Globo-N-triaosylceramide | HMDB | Globotriaosylceramide | HMDB | Globotriglycosylceramide | HMDB | Globotriosylceramide | HMDB | Shiga toxin receptor | HMDB |
|
---|
Chemical Formula | C48H89NO18 |
---|
Average Molecular Mass | 968.216 g/mol |
---|
Monoisotopic Mass | 967.608 g/mol |
---|
CAS Registry Number | 71965-57-6 |
---|
IUPAC Name | N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanamide |
---|
Traditional Name | N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanamide |
---|
SMILES | 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]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC |
---|
InChI Identifier | InChI=1S/C48H89NO18/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-32(53)31(49-36(54)26-24-22-20-17-12-10-8-6-4-2)30-62-46-42(60)39(57)44(34(28-51)64-46)67-48-43(61)40(58)45(35(29-52)65-48)66-47-41(59)38(56)37(55)33(27-50)63-47/h23,25,31-35,37-48,50-53,55-61H,3-22,24,26-30H2,1-2H3,(H,49,54)/b25-23+/t31-,32+,33+,34+,35+,37-,38-,39+,40+,41+,42+,43+,44+,45-,46+,47+,48-/m0/s1 |
---|
InChI Key | HJVQASFQICDJJP-GJXDXCKOSA-N |
---|
Chemical Taxonomy |
---|
Description | 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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Sphingolipids |
---|
Sub Class | Glycosphingolipids |
---|
Direct Parent | Glycosyl-N-acylsphingosines |
---|
Alternative Parents | |
---|
Substituents | - Glycosyl-n-acylsphingosine
- Oligosaccharide
- Fatty acyl glycoside
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- N-acyl-amine
- Oxane
- Fatty acyl
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Oxacycle
- Polyol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Primary alcohol
- Alcohol
- Organopnictogen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Carbonyl group
- Organooxygen compound
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Not Available |
---|
Cellular Locations | Not Available |
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ugu-0100408819-34a11a7e6e1fd70d3862 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03g0-0300709501-ef8ac402e8d8041f34a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-0801409311-b691ef3b3a9d2f7985a2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00kb-0410403219-693a63badcb884ed8482 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dv-3712209416-14260e86f9064bbbeafb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-4911116000-5a70a7d6a9a8960e37d0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0n2a-3702302119-8c26a66d0c4fa6705f6e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03gi-1901201102-d45beaa25e8b41859201 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06r7-6900200000-fd918736c1c45d4e6a46 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000001019-88b3e1b2524a342e4b71 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-2401101139-5ed70149659da5bbc457 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0m0y-4952815020-2a3aaef7e17eb0449a06 | Spectrum |
|
---|
Toxicity Profile |
---|
Route of Exposure | Not Available |
---|
Mechanism of Toxicity | Not Available |
---|
Metabolism | Not Available |
---|
Toxicity Values | Not Available |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | Not Available |
---|
Uses/Sources | Not Available |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Not Available |
---|
Symptoms | Not Available |
---|
Treatment | Not Available |
---|
Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB0004877 |
---|
FooDB ID | FDB023470 |
---|
Phenol Explorer ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
BiGG ID | Not Available |
---|
BioCyc ID | D-GALACTOSYL-14-D-GALACTOSYL-14-D- |
---|
METLIN ID | 7134 |
---|
PDB ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
Chemspider ID | 30776565 |
---|
ChEBI ID | Not Available |
---|
PubChem Compound ID | 53477785 |
---|
Kegg Compound ID | C04737 |
---|
YMDB ID | Not Available |
---|
ECMDB ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
MSDS | Not Available |
---|
General References | 1. Ogawa, Tomoya; Koike, Katsuya; Numata, Masaaki; Sugimoto, Mamoru; Nakahara, Yoshiaki. Preparation of a neutral glycosphingolipid as a globotriaosylceramide analog useful in diagnosis and treatment of malignancy. Jpn. Kokai Tokkyo Koho (1988), 18 | 2. Ogawa, Tomoya; Koike, Katsuya; Numata, Masaaki; Sugimoto, Mamoru; Nakahara, Yoshiaki. Preparation of a neutral glycosphingolipid as a globotriaosylceramide analog useful in diagnosis and treatment of malignancy. Jpn. Kokai Tokkyo Koho (1988), 18 | 3. Hara A, Kitazawa N, Taketomi T: Abnormalities of glycosphingolipids in mucopolysaccharidosis type III B. J Lipid Res. 1984 Feb;25(2):175-84. | 4. 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. | 5. Thurberg BL, Randolph Byers H, Granter SR, Phelps RG, Gordon RE, O'Callaghan M: Monitoring the 3-year efficacy of enzyme replacement therapy in fabry disease by repeated skin biopsies. J Invest Dermatol. 2004 Apr;122(4):900-8. | 6. 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. | 7. Thurberg BL, Rennke H, Colvin RB, Dikman S, Gordon RE, Collins AB, Desnick RJ, O'Callaghan M: Globotriaosylceramide accumulation in the Fabry kidney is cleared from multiple cell types after enzyme replacement therapy. Kidney Int. 2002 Dec;62(6):1933-46. | 8. Kovbasnjuk O, Mourtazina R, Baibakov B, Wang T, Elowsky C, Choti MA, Kane A, Donowitz M: The glycosphingolipid globotriaosylceramide in the metastatic transformation of colon cancer. Proc Natl Acad Sci U S A. 2005 Dec 27;102(52):19087-92. Epub 2005 Dec 19. | 9. Roder B, Dabrowski J, Dabrowski U, Egge H, Peter-Katalinic J, Schwarzmann G, Sandhoff K: The determination of phytosphingosine-containing globotriaosylceramide from human kidney in the presence of lactosylceramide. Chem Phys Lipids. 1990 Mar;53(1):85-9. | 10. Eng CM, Guffon N, Wilcox WR, Germain DP, Lee P, Waldek S, Caplan L, Linthorst GE, Desnick RJ: Safety and efficacy of recombinant human alpha-galactosidase A replacement therapy in Fabry's disease. N Engl J Med. 2001 Jul 5;345(1):9-16. | 11. Wenger DA, DeGala G, Williams C, Taylor HA, Stevenson RE, Pruitt JR, Miller J, Garen PD, Balentine JD: Clinical, pathological, and biochemical studies on an infantile case of sulfatide/GM1 activator protein deficiency. Am J Med Genet. 1989 Jun;33(2):255-65. | 12. Abe A, Wild SR, Lee WL, Shayman JA: Agents for the treatment of glycosphingolipid storage disorders. Curr Drug Metab. 2001 Sep;2(3):331-8. | 13. Mignani R, Cagnoli L: Enzyme replacement therapy in Fabry's disease: recent advances and clinical applications. J Nephrol. 2004 May-Jun;17(3):354-63. | 14. Kanekura T, Fukushige T, Kanda A, Tsuyama S, Murata F, Sakuraba H, Kanzaki T: Immunoelectron-microscopic detection of globotriaosylceramide accumulated in the skin of patients with Fabry disease. Br J Dermatol. 2005 Sep;153(3):544-8. | 15. Li SC, Kundu SK, Degasperi R, Li YT: Accumulation of globotriaosylceramide in a case of leiomyosarcoma. Biochem J. 1986 Dec 15;240(3):925-7. | 16. Wilcox WR, Banikazemi M, Guffon N, Waldek S, Lee P, Linthorst GE, Desnick RJ, Germain DP: Long-term safety and efficacy of enzyme replacement therapy for Fabry disease. Am J Hum Genet. 2004 Jul;75(1):65-74. Epub 2004 May 20. |
|
---|