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Record Information
Version2.0
Created at2022-09-06 05:01:12 UTC
Updated at2022-09-06 05:01:12 UTC
NP-MRD IDNP0226091
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4r,5s,6s,7s,11s)-7-hydroxy-6-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undec-1(10)-en-2-one
Description(4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undec-1(10)-en-2-one belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (4r,5s,6s,7s,11s)-7-hydroxy-6-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undec-1(10)-en-2-one is found in Gelsemium sempervirens. Based on a literature review very few articles have been published on (4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undec-1(10)-en-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H22O10
Average Mass374.3420 Da
Monoisotopic Mass374.12130 Da
IUPAC Name(4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one
Traditional Name(4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undec-1(10)-en-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2OC(=O)C3=COC[C@@]1(O)[C@H]23
InChI Identifier
InChI=1S/C16H22O10/c1-5-12(26-15-11(20)10(19)9(18)7(2-17)24-15)13-8-6(14(21)25-13)3-23-4-16(5,8)22/h3,5,7-13,15,17-20,22H,2,4H2,1H3/t5-,7+,8-,9+,10-,11+,12-,13+,15-,16-/m0/s1
InChI KeyAZDPGDNGMGSZEZ-MGFQIBOVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gelsemium sempervirensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Furopyran
  • Gamma butyrolactone
  • Monosaccharide
  • Oxane
  • Pyran
  • Cyclic alcohol
  • Furan
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • 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
logP-2.8ChemAxon
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity80.67 m³·mol⁻¹ChemAxon
Polarizability35.06 ųChemAxon
Number of Rings4ChemAxon
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 Compound162951626
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]