Show more...
Record Information
Version2.0
Created at2022-09-07 09:25:39 UTC
Updated at2022-09-07 09:25:39 UTC
NP-MRD IDNP0247539
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-[(6z,9z,12z,15z)-octadeca-6,9,12,15-tetraenoyloxy]-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (3z,6z,9z,12z,15z)-octadeca-3,6,9,12,15-pentaenoate
DescriptionDgdg(18:5(3Z,6z,9z,12z,15z)/18:4(6Z,9z,12z,15z)) belongs to the class of organic compounds known as 3-o-beta-d-digalactosyl-sn-glycerols. These are glycosylglycerols carrying a beta-D-digalactose at the 3-position of the glycerol moiety. Thus, DGDG(18:5(3Z,6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycosyldiradylglycerol. (2s)-2-[(6z,9z,12z,15z)-octadeca-6,9,12,15-tetraenoyloxy]-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (3z,6z,9z,12z,15z)-octadeca-3,6,9,12,15-pentaenoate is found in Heterocapsa circularisquama. Based on a literature review very few articles have been published on Dgdg(18:5(3Z,6z,9z,12z,15z)/18:4(6Z,9z,12z,15z)).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC51H78O15
Average Mass931.1700 Da
Monoisotopic Mass930.53407 Da
IUPAC Name(2S)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate
Traditional Name(2S)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(=O)O[C@@H](CO[C@@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O)COC(=O)C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C51H78O15/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-42(53)61-36-39(64-43(54)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)37-62-50-49(60)47(58)45(56)41(66-50)38-63-51-48(59)46(57)44(55)40(35-52)65-51/h5-8,11-14,17-20,23-26,29,31,39-41,44-52,55-60H,3-4,9-10,15-16,21-22,27-28,30,32-38H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-/t39-,40-,41-,44+,45+,46+,47+,48-,49-,50-,51+/m1/s1
InChI KeyIXGDAVSSYHYPJX-GNQOIDSESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Heterocapsa circularisquamaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-o-beta-d-digalactosyl-sn-glycerols. These are glycosylglycerols carrying a beta-D-digalactose at the 3-position of the glycerol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassGlycosylglycerols
Direct Parent3-O-beta-D-digalactosyl-sn-glycerols
Alternative Parents
Substituents
  • 3-o-beta-d-digalactosyl-sn-glycerol
  • Glycosyldiacylglycerol
  • Glycosyldiradylglycerol
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Octadecanoid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acid ester
  • Oxane
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.98ChemAxon
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area231.13 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity260.98 m³·mol⁻¹ChemAxon
Polarizability99.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9106262
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10931024
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]