Show more...
Record Information
Version2.0
Created at2022-09-02 11:33:52 UTC
Updated at2022-09-02 11:33:53 UTC
NP-MRD IDNP0154618
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate
Description[(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. [(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Campsis grandiflora. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(2R,3R,4S,5R,6S)-6-{[(1S,4as,6S,7R,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetic acidGenerator
Chemical FormulaC26H34O15
Average Mass586.5430 Da
Monoisotopic Mass586.18977 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C(C=O)[C@H]3C[C@H](OC(C)=O)[C@](C)(O)[C@@H]23)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
InChI Identifier
InChI=1S/C26H34O15/c1-11(28)34-10-18-21(37-13(3)30)22(38-14(4)31)23(39-15(5)32)25(40-18)41-24-20-17(16(8-27)9-35-24)7-19(26(20,6)33)36-12(2)29/h8-9,17-25,33H,7,10H2,1-6H3/t17-,18-,19+,20-,21-,22+,23-,24+,25+,26+/m1/s1
InChI KeyQTUVOXCKBFYKTE-YQWDYXRPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Campsis grandifloraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentIridoid O-glycosides
Alternative Parents
Substituents
  • Iridoid o-glycoside
  • Pentacarboxylic acid or derivatives
  • Glycosyl compound
  • Iridoid-skeleton
  • O-glycosyl compound
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Vinylogous ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aldehyde
  • 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
logP0.74ALOGPS
logP-1.1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area196.49 ŲChemAxon
Rotatable Bond Count14ChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10218881
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21594951
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]