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Record Information
Version1.0
Created at2022-09-12 17:03:37 UTC
Updated at2022-09-12 17:03:37 UTC
NP-MRD IDNP0331073
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s,4s,4ar,17r,18ar)-17-hexyl-3,4-dihydroxy-2-(hydroxymethyl)-hexadecahydropyrano[2,3-b]1,4-dioxacyclohexadecan-6-one
DescriptionGallicaside H belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (2r,3s,4s,4ar,17r,18ar)-17-hexyl-3,4-dihydroxy-2-(hydroxymethyl)-hexadecahydropyrano[2,3-b]1,4-dioxacyclohexadecan-6-one is found in Silene gallica. Based on a literature review very few articles have been published on Gallicaside H.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H44O7
Average Mass444.6090 Da
Monoisotopic Mass444.30870 Da
IUPAC Name(2R,3S,4S,4aR,17R,18aR)-17-hexyl-3,4-dihydroxy-2-(hydroxymethyl)-hexadecahydro-2H-pyrano[2,3-b]1,4-dioxacyclohexadecan-6-one
Traditional Name(2R,3S,4S,4aR,17R,18aR)-17-hexyl-3,4-dihydroxy-2-(hydroxymethyl)-hexadecahydropyrano[2,3-b]1,4-dioxacyclohexadecan-6-one
CAS Registry NumberNot Available
SMILES
CCCCCC[C@@H]1CCCCCCCCCCC(=O)O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O1
InChI Identifier
InChI=1S/C24H44O7/c1-2-3-4-11-14-18-15-12-9-7-5-6-8-10-13-16-20(26)31-23-22(28)21(27)19(17-25)30-24(23)29-18/h18-19,21-25,27-28H,2-17H2,1H3/t18-,19-,21-,22+,23-,24-/m1/s1
InChI KeyOXPUVXANXMWSSL-MAIAYQQESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Silene gallicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSaccharolipids
Sub ClassNot Available
Direct ParentSaccharolipids
Alternative Parents
Substituents
  • Saccharolipid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Macrolide
  • Alkyl glycoside
  • Monosaccharide
  • Oxane
  • Fatty acyl
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP4.65ChemAxon
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.88 m³·mol⁻¹ChemAxon
Polarizability51.02 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101519839
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]