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15639-50-6 | 1,3-Octadecanediol, 2-amino-, (2S,3S)-
CAS No: 15639-50-6 Catalog No: AG001OPT MDL No:MFCD00792847
Product Description
Catalog Number:
AG001OPT
Chemical Name:
1,3-Octadecanediol, 2-amino-, (2S,3S)-
CAS Number:
15639-50-6
Molecular Formula:
C18H39NO2
Molecular Weight:
301.5078
MDL Number:
MFCD00792847
IUPAC Name:
(2S,3S)-2-aminooctadecane-1,3-diol
InChI:
InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1
InChI Key:
OTKJDMGTUTTYMP-ROUUACIJSA-N
SMILES:
CCCCCCCCCCCCCCC[C@@H]([C@H](CO)N)O
EC Number:
608-571-3
UNII:
OWA98U788S
NSC Number:
714503
Properties
Complexity:
200
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
301.298g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
301.515g/mol
Monoisotopic Mass:
301.298g/mol
Rotatable Bond Count:
16
Topological Polar Surface Area:
66.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.8
Literature
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| Deletion of IFN-gamma reduces fumonisin-induced hepatotoxicity in mice via alterations in inflammatory cytokines and apoptotic factors. | Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research 20030101 |
| A protein kinase Cbeta inhibitor attenuates multidrug resistance of neuroblastoma cells. | BMC cancer 20030101 |
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| Fumonisins and fumonisin analogs as inhibitors of ceramide synthase and inducers of apoptosis. | Biochimica et biophysica acta 20021230 |
| Cholecystokinin-stimulated tyrosine phosphorylation of PKC-delta in pancreatic acinar cells is regulated bidirectionally by PKC activation. | Biochimica et biophysica acta 20021216 |
| Comparison of the toxicity of several fumonisin derivatives in a 28-day feeding study with female B6C3F(1) mice. | Toxicology and applied pharmacology 20021215 |
| Isolation and characterization of the genes encoding delta(8)-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis. | Current microbiology 20021201 |
| Host resistance to Trypanosoma cruzi infection is enhanced in mice fed Fusarium verticillioides (=F. moniliforme) culture material containing fumonisins. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20021201 |
| Prolonged activation of Ca2+-activated K+ current contributes to the long-lasting refractory period of Aplysia bag cell neurons. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20021201 |
| Participation of protein kinase C alpha isoform and extracellular signal-regulated kinase in neurite outgrowth of GT1 hypothalamic neurons. | Journal of neurochemistry 20021201 |
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| Comparative study of naphthalene-2,3-dicarboxaldehyde and o-phthalaldehyde fluorogenic reagents for chromatographic detection of sphingoid bases. | Journal of chromatography. A 20021115 |
| Yeast cells lacking the ARV1 gene harbor defects in sphingolipid metabolism. Complementation by human ARV1. | The Journal of biological chemistry 20020927 |
| Fumonisin B(1) alters sphingolipid metabolism and tumor necrosis factor alpha expression in heart and lung of mice. | Life sciences 20020913 |
| A role for the de novo sphingolipids in apoptosis of photosensitized cells. | Experimental cell research 20020910 |
| Effect of acute exercise on the content of free sphinganine and sphingosine in different skeletal muscle types of the rat. | Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20020901 |
| Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells. | Experimental biology and medicine (Maywood, N.J.) 20020501 |
| Dihydroceramide desaturase activity in tumors. | Biochemistry. Biokhimiia 20020501 |
| Pharmacological antagonism of fumonisin B1 cytotoxicity in porcine renal epithelial cells (LLC-PK1): a model for reducing fumonisin-induced nephrotoxicity in vivo. | Pharmacology & toxicology 20020501 |
| Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy. | Biophysical journal 20020401 |
| 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol, a substrate for human sphingosine kinase. | Biochimica et biophysica acta 20020130 |
| Targeting protein kinase C: new therapeutic opportunities against high-grade malignant gliomas? | The oncologist 20020101 |
| [Biologically effective sphingolipids devoid of 4-trans-double bond in the sphingoid hydrocarbon chain]. | Bioorganicheskaia khimiia 20020101 |
| Antitumor activity of protein kinase C inhibitors and cisplatin in human head and neck squamous cell carcinoma lines. | Anti-cancer drugs 20020101 |
| Dependence of the sphingoid bases concentration on growth phase and temperature in the yeast Yarrowia lipolytica. | Journal of basic microbiology 20020101 |
| Depolarisation induces rapid and transient formation of intracellular sphingosine-1-phosphate. | FEBS letters 20011207 |
| Sphingolipids as biomarkers of fumonisin exposure and risk of esophageal squamous cell carcinoma in china. | Cancer causes & control : CCC 20011101 |
| Characterization of an Arabidopsis cDNA encoding a subunit of serine palmitoyltransferase, the initial enzyme in sphingolipid biosynthesis. | Plant & cell physiology 20011101 |
| [Survey on the fumonisins intake and the urinary Sa/So ratio of people suffered from a high incidence of esophageal cancer]. | Wei sheng yan jiu = Journal of hygiene research 20011101 |
| Fumonisin B(1) induces apoptosis in LLC-PK(1) renal epithelial cells via a sphinganine- and calmodulin-dependent pathway. | Toxicology and applied pharmacology 20011015 |
| The induction and persistence of altered sphingolipid biosynthesis in rats treated with fumonisin B1. | Food additives and contaminants 20010901 |
| Gender-related differences in subacute fumonisin B1 hepatotoxicity in BALB/c mice. | Toxicology 20010828 |
| Reaction of fumonisin with glucose prevents promotion of hepatocarcinogenesis in female F344/N rats while maintaining normal hepatic sphinganine/sphingosine ratios. | Journal of agricultural and food chemistry 20010801 |
| The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. | Toxicon : official journal of the International Society on Toxinology 20010701 |
| TNF-alpha-induced sphingosine 1-phosphate inhibits apoptosis through a phosphatidylinositol 3-kinase/Akt pathway in human hepatocytes. | Journal of immunology (Baltimore, Md. : 1950) 20010701 |
| N-(4-hydroxyphenyl)retinamide elevates ceramide in neuroblastoma cell lines by coordinate activation of serine palmitoyltransferase and ceramide synthase. | Cancer research 20010701 |
| Fumonisin-induced tumor necrosis factor-alpha expression in a porcine kidney cell line is independent of sphingoid base accumulation induced by ceramide synthase inhibition. | Toxicology and applied pharmacology 20010701 |
| C26-CoA-dependent ceramide synthesis of Saccharomyces cerevisiae is operated by Lag1p and Lac1p. | The EMBO journal 20010601 |
| Toxicity of Fusarium moniliforme culture material containing known levels of fumonisin B1 in ducks. | Toxicology 20010528 |
| Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase. | The Journal of biological chemistry 20010518 |
| The effect of a single gavage dose of fumonisin B(2) on the sphinganine and sphingosine concentrations in vervet monkeys. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010501 |
| Ineffectiveness of activated carbon in reducing the alteration of sphingolipid metabolism in rats exposed to fumonisin-contaminated diets. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010501 |
| Sphingolipid perturbations as mechanisms for fumonisin carcinogenesis. | Environmental health perspectives 20010501 |
| Sphinganine in sphingomyelins of tumors and mouse regenerating liver. | Biochemistry. Biokhimiia 20010501 |
| High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. | Journal of chromatography. B, Biomedical sciences and applications 20010425 |
| Functional identification of a delta8-sphingolipid desaturase from Borago officinalis. | Archives of biochemistry and biophysics 20010415 |
| Fumonisin B(1) increases serum sphinganine concentration but does not alter serum sphingosine concentration or induce cardiovascular changes in milk-fed calves. | Toxicological sciences : an official journal of the Society of Toxicology 20010401 |
| Fumonisin B(1) is hepatotoxic and nephrotoxic in milk-fed calves. | Toxicological sciences : an official journal of the Society of Toxicology 20010401 |
| Fumonisin B1 promotes aflatoxin B1 and N-methyl-N'-nitro-nitrosoguanidine-initiated liver tumors in rainbow trout. | Toxicology and applied pharmacology 20010401 |
| Differential effects of fumonisin B1 on cell death in cultured cells: the significance of the elevated sphinganine. | Archives of pharmacal research 20010401 |
| Targeting ceramide metabolism--a strategy for overcoming drug resistance. | Journal of the National Cancer Institute 20010307 |
| A mechanistic approach to modelling the risk of liver tumours in mice exposed to fumonisin B1 in the diet. | Food additives and contaminants 20010301 |
| Tissue sphinganine as a biomarker of fumonisin-induced apoptosis. | Food additives and contaminants 20010301 |
| Determination of sphinganine, sphingosine and Sa/So ratio in urine of humans exposed to dietary fumonisin B1. | Food additives and contaminants 20010301 |
| Comparison of the metabolism of L-erythro- and L-threo-sphinganines and ceramides in cultured cells and in subcellular fractions. | Biochimica et biophysica acta 20010226 |
| Regulation of phospholipase D (PLD) in growth plate chondrocytes by 24R,25-(OH)2D3 is dependent on cell maturation state (resting zone cells) and is specific to the PLD2 isoform. | Biochimica et biophysica acta 20010115 |
| The effect of a single gavage dose of fumonisin B(1) on the sphinganine and sphingosine levels in vervet monkeys. | Toxicon : official journal of the International Society on Toxinology 20010101 |
| Modulation of protein kinase C in antitumor treatment. | Reviews of physiology, biochemistry and pharmacology 20010101 |
| Activation of sphingosine kinase by the bradykinin B2 receptor and its implication in regulation of the ERK/MAP kinase pathway. | Biological chemistry 20010101 |
| In vitro and in vivo studies to assess the effectiveness of cholestyramine as a binding agent for fumonisins. | Mycopathologia 20010101 |
| Benzene and its metabolite, hydroquinone, induce granulocytic differentiation in myeloblasts by interacting with cellular signaling pathways activated by granulocyte colony-stimulating factor. | Stem cells (Dayton, Ohio) 19950501 |
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