Structure via PubChem · Public domain (PubChem)
melezitose
Sign in to saveAlso known as Melizitose, O-alpha-D-glucopyranosyl-(1-3)-beta-D-fructofuranosyl-alpha-D-glucopyranoside, (2R,3R,4S,5S,6R)-2-{[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol, D-melezitose, melicitose, D-(+)-melezitose
Melezitose, also spelled melicitose, is a nonreducing trisaccharide sugar that is produced by many plant sap eating insects, including aphids such as Cinara pilicornis, by an enzyme reaction. This is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees although it is not easily digestible by bees. This is useful to the aphids as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the lat
In the Vinony graph
Within Vinony's link graph, melezitose is referenced by 138 other articles, and connects out to hexose, Formicidae and insect.
It sits within the topics Chembox image size set, ECHA InfoCard ID from Wikidata and Trisaccharides.
Its subject is documented across 19 Wikipedia language editions.
Chemical data
- Formula
- C18H32O16
- Molecular weight
- 504.4 g/mol
- IUPAC name
- (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O)O)O)O
- InChIKey
- QWIZNVHXZXRPDR-WSCXOGSTSA-N
- XLogP
- -5.8
- Polar surface area
- 269 Ų
- H-bond donors
- 11
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- trisaccharide
- Has part
- hydrogen
- Mass
- 504.169035
Show 4 more facts
- chemical formula
- C₁₈H₃₂O₁₆
- found in taxon
- Caenorhabditis elegans
- isomeric SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O)O)O)O
- canonical SMILES
- C(C1C(C(C(C(O1)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O)O)O)O)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{Chembox | Verifiedfields = changed | verifiedrevid = 458280958 | ImageFile=Melezitose.png | ImageSize=200px | IUPACName=α-D-Glucopyranosyl α-D-glucopyranosyl-(1→3)-β-D-fructofuranoside | SystematicName=(2R,2′R,3R,3′R,4S,4′S,5S,5′S,6R,6′R)-2,2′-{[(2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)oxolane-2,3-diyl]bis(oxy)}bis[6-(hydroxymethyl)oxane-3,4,5-triol] | OtherNames=Melicitose |Section1= |Section2= |Section3= }}
Melezitose, also spelled melicitose, is a nonreducing trisaccharide sugar that is produced by many plant sap eating insects, including aphids such as Cinara pilicornis, by an enzyme reaction. This is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees although it is not easily digestible by bees. This is useful to the aphids as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the latter of which is an isomer of sucrose.
Excerpted from Wikipedia’s “melezitose” article, available under the CC BY-SA 4.0 licence.