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Record Information
Version2.0
Created at2022-09-11 18:55:24 UTC
Updated at2022-09-11 18:55:24 UTC
NP-MRD IDNP0318429
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3r,5s,7r,9s,10s,12r,14s,15r,18r,19r,20r,22s,23r)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate
Description(1S,3R,5S,7R,9S,10S,12R,14S,15R,18R,19R,20R,22S,23R)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-20-yl acetate belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (1s,3r,5s,7r,9s,10s,12r,14s,15r,18r,19r,20r,22s,23r)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate is found in Asclepias vestita. Based on a literature review very few articles have been published on (1S,3R,5S,7R,9S,10S,12R,14S,15R,18R,19R,20R,22S,23R)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-20-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S,3R,5S,7R,9S,10S,12R,14S,15R,18R,19R,20R,22S,23R)-9-(Acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0,.0,.0,.0,]pentacosan-20-yl acetic acidGenerator
Chemical FormulaC32H44O11
Average Mass604.6930 Da
Monoisotopic Mass604.28836 Da
IUPAC Name(1S,3R,5S,7R,9S,10S,12R,14S,15R,18R,19R,20R,22S,23R)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate
Traditional Name(1S,3R,5S,7R,9S,10S,12R,14S,15R,18R,19R,20R,22S,23R)-9-(acetyloxy)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-20-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@@H]1C[C@H](OC(C)=O)[C@]2(O)O[C@@H]3C[C@H]4[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H]([C@@H](C[C@]54O)OC(C)=O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1
InChI Identifier
InChI=1S/C32H44O11/c1-15-9-26(41-17(3)34)32(37)29(39-15)42-23-10-18-5-6-22-20(21(18)12-24(23)43-32)7-8-30(4)28(19-11-27(35)38-14-19)25(40-16(2)33)13-31(22,30)36/h11,15,18,20-26,28-29,36-37H,5-10,12-14H2,1-4H3/t15-,18+,20-,21+,22-,23-,24-,25-,26+,28+,29+,30-,31+,32+/m1/s1
InChI KeyOIQCHMSGQYKBPX-JQAAHPLESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Asclepias vestitaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative Parents
Substituents
  • Steroid lactone
  • Steroid ester
  • Estrane-skeleton
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Tricarboxylic acid or derivatives
  • Para-dioxane
  • 2-furanone
  • Oxane
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • 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
logP2.13ChemAxon
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area147.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity148.11 m³·mol⁻¹ChemAxon
Polarizability64.57 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
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 Compound163010204
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]