Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:49:25 UTC
Update Date2022-08-31 17:38:21 UTC
Metabolite IDMMDBc0029984
Metabolite Identification
Common Name2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Description2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Lipid X is a diacylglucosamine 1-phosphate bearing beta-hydroxymyristoyl groups at positions 2 and 3. (PMID 2998869 ) The simplest of these, lipid X, is a derivative of glucosamine-1-phosphate substituted with beta-hydroxymyristoyl moieties at positions 2 and 3. (PMID 6382553 ) Lipid X (2,3-diacylglucosamine-1-phosphate) is a novel monosaccharide precursor of lipid A that has some of the physiologic activities of endotoxin but little toxicity. Perhaps because lipid X is a subunit of lipid A, lipid X shows a partial pyrogenic effect while also decreasing the pyrogenic activity of complete lipopolysaccharide (LPS). Lipid X is a potential prototype compound for a new type of chemotherapy directed at blocking the harmful effects of LPS during bacterial septicemia. (PMID 3308707 ) A monosaccharide precursor of Escherichia coli lipid A, designated lipid X, which is a diacylglucosamine 1-phosphate with beta-hydroxymyristoyl groups at positions 2 and 3, was shown to have the ability to induce the production of tumor necrosis factor (TNF)-like tumor-cytotoxic factor by a murine macrophage-like cell line, J774. (PMID 3701065 )
Structure
Synonyms
ValueSource
2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphateGenerator
2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphateGenerator
2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acidGenerator
Molecular FormulaC34H66NO12P
Average Mass711.8611
Monoisotopic Mass711.432263093
IUPAC Name3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]tetradecanimidic acid
Traditional Name3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]-2-(phosphonooxy)oxan-3-yl]tetradecanimidic acid
CAS Registry NumberNot Available
SMILES
[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26?,27?,28-,31-,32-,33-,34-/m1/s1
InChI KeyHEHQDWUWJVPREQ-JIMHHRIFSA-N