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Record Information
Version2.0
Created at2022-09-10 19:17:43 UTC
Updated at2022-09-10 19:17:44 UTC
NP-MRD IDNP0304300
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-hydroxy-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 (9z,12z)-octadeca-9,12-dienoate
DescriptionGingerglycolipid b belongs to the class of organic compounds known as 1-acyl-3-o-beta-d-digalactosyl-sn-glycerols. These are glycosylmonoacylglycerols carrying a beta-D-digalactose at the 3-position of the glycerol moiety and a fatty acyl at the O-1 position of the glycerol moiety. Thus, gingerglycolipid b is considered to be a glycosylmonoradylglycerol. (2s)-2-hydroxy-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 (9z,12z)-octadeca-9,12-dienoate is found in Zingiber officinale. (2s)-2-hydroxy-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 (9z,12z)-octadeca-9,12-dienoate was first documented in 2012 (PMID: 23263807). Based on a literature review a small amount of articles have been published on Gingerglycolipid b (PMID: 24273867) (PMID: 36076393).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H58O14
Average Mass678.8130 Da
Monoisotopic Mass678.38266 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)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
InChI Identifier
InChI=1S/C33H58O14/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-25(36)43-19-22(35)20-44-32-31(42)29(40)27(38)24(47-32)21-45-33-30(41)28(39)26(37)23(18-34)46-33/h6-7,9-10,22-24,26-35,37-42H,2-5,8,11-21H2,1H3/b7-6-,10-9-/t22-,23-,24-,26+,27+,28+,29+,30-,31-,32-,33+/m1/s1
InChI KeyUHISGSDYAIIBMO-UMLSMIIMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acyl-3-o-beta-d-digalactosyl-sn-glycerols. These are glycosylmonoacylglycerols carrying a beta-D-digalactose at the 3-position of the glycerol moiety and a fatty acyl at the O-1 position of the glycerol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassGlycosylglycerols
Direct Parent1-acyl-3-O-beta-D-digalactosyl-sn-glycerols
Alternative Parents
Substituents
  • 1-acyl-3-o-beta-d-digalactosyl-sn-glycerol
  • Glycosylmonoacylglycerol
  • Glycosylmonoradylglycerol
  • Octadecanoid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Monocarboxylic acid or derivatives
  • Polyol
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8185334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10009754
PDB IDNot Available
ChEBI ID184627
Good Scents IDNot Available
References
General References
  1. Tarawneh AH, Leon F, Radwan MM, Rosa LH, Cutler SJ: Secondary metabolites from the fungus Emericella nidulans. Nat Prod Commun. 2013 Sep;8(9):1285-8. [PubMed:24273867 ]
  2. Xiong Q, Zhang J, Shi Q, Zhang Y, Sun C, Li A, Lu W, Hu J, Zhou N, Wei H, Wang S, Zhang H, Zhu J: The key metabolites associated with nutritional components in purple glutinous rice. Food Res Int. 2022 Oct;160:111686. doi: 10.1016/j.foodres.2022.111686. Epub 2022 Jul 14. [PubMed:36076393 ]
  3. Kiem PV, Minh CV, Nhiem NX, Cuong NX, Tai BH, Quang TH, Anh Hle T, Yen PH, Ban NK, Kim SH, Xin M, Cha JY, Lee YM, Kim YH: Inhibitory effect on TNF-alpha-induced IL-8 secretion in HT-29 cell line by glyceroglycolipids from the leaves of Ficus microcarpa. Arch Pharm Res. 2012 Dec;35(12):2135-42. doi: 10.1007/s12272-012-1210-8. Epub 2012 Dec 21. [PubMed:23263807 ]
  4. LOTUS database [Link]