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Record Information
Version2.0
Created at2022-04-29 00:18:48 UTC
Updated at2022-04-29 00:18:48 UTC
NP-MRD IDNP0079276
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Riisein B
Description(2R,6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5-{[(2S,3S,4S,5R)-5-(acetyloxy)-3,4-dihydroxyoxan-2-yl]oxy}-7,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2-methylheptyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (-)-Riisein B is found in Carijoa riisei. Based on a literature review very few articles have been published on (2R,6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5-{[(2S,3S,4S,5R)-5-(acetyloxy)-3,4-dihydroxyoxan-2-yl]oxy}-7,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2-methylheptyl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R,6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5-{[(2S,3S,4S,5R)-5-(acetyloxy)-3,4-dihydroxyoxan-2-yl]oxy}-7,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-2-methylheptyl acetic acidGenerator
Chemical FormulaC36H60O10
Average Mass652.8660 Da
Monoisotopic Mass652.41865 Da
IUPAC Name(2R,6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5-{[(2S,3S,4S,5R)-5-(acetyloxy)-3,4-dihydroxyoxan-2-yl]oxy}-7,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl acetate
Traditional Name(2R,6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5-{[(2S,3S,4S,5R)-5-(acetyloxy)-3,4-dihydroxyoxan-2-yl]oxy}-7,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl acetate
CAS Registry NumberNot Available
SMILES
C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1OC[C@@H](OC(C)=O)[C@@H](O)[C@@H]1O)COC(C)=O
InChI Identifier
InChI=1S/C36H60O10/c1-20(18-43-22(3)37)8-7-9-21(2)26-10-11-27-25-16-30(39)36(42)17-24(12-15-35(36,6)28(25)13-14-34(26,27)5)46-33-32(41)31(40)29(19-44-33)45-23(4)38/h20-21,24-33,39-42H,7-19H2,1-6H3/t20-,21-,24+,25+,26-,27+,28+,29-,30-,31-,32+,33+,34-,35-,36+/m1/s1
InChI KeyWHLJRKVSRAHTRJ-GHABPAFDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carijoa riisei-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Steroid ester
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • Glycosyl compound
  • O-glycosyl compound
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen 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
logP3.75ALOGPS
logP3.59ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.24ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area151.98 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity169.22 m³·mol⁻¹ChemAxon
Polarizability75.48 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 Compound163006906
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available