Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:55:24 UTC
Update Date2022-08-31 18:26:31 UTC
Metabolite IDMMDBc0031929
Metabolite Identification
Common NameLipid IIA
DescriptionA lipid A derivative in which the phospho group at the anomeric carbon is esterified with a 4-amino-4-deoxy-β-L-arabinopyranosyl group
Structure
Synonyms
ValueSource
4-Amino-4-deoxy-beta-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-alpha-D-glucopyranosyl hydrogen phosphateChEBI
4-Amino-4-deoxy-b-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-b-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-a-D-glucopyranosyl hydrogen phosphateGenerator
4-Amino-4-deoxy-b-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-b-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-a-D-glucopyranosyl hydrogen phosphoric acidGenerator
4-Amino-4-deoxy-beta-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-alpha-D-glucopyranosyl hydrogen phosphoric acidGenerator
4-Amino-4-deoxy-β-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-α-D-glucopyranosyl hydrogen phosphateGenerator
4-Amino-4-deoxy-β-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-α-D-glucopyranosyl hydrogen phosphoric acidGenerator
Molecular FormulaC73H139N3O26P2
Average Mass1536.858
Monoisotopic Mass1535.912205604
IUPAC Name{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]methoxy}-2-(hydroxymethyl)-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid
Traditional Namelipid iia
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(=O)O[C@H]2OC[C@H](N)[C@H](O)[C@H]2O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@H]2NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C73H139N3O26P2/c1-5-9-13-17-21-25-29-33-37-41-52(78)45-59(82)75-63-69(98-61(84)47-54(80)43-39-35-31-27-23-19-15-11-7-3)66(87)58(97-72(63)101-104(92,93)102-73-67(88)65(86)56(74)50-94-73)51-95-71-64(76-60(83)46-53(79)42-38-34-30-26-22-18-14-10-6-2)70(68(57(49-77)96-71)100-103(89,90)91)99-62(85)48-55(81)44-40-36-32-28-24-20-16-12-8-4/h52-58,63-73,77-81,86-88H,5-51,74H2,1-4H3,(H,75,82)(H,76,83)(H,92,93)(H2,89,90,91)/t52-,53-,54-,55-,56+,57-,58-,63-,64-,65+,66-,67-,68-,69-,70-,71-,72-,73-/m1/s1
InChI KeyTYGQMXOPLFWYPM-ISFHUDAKSA-N