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Record Information
Version2.0
Created at2022-09-10 10:10:23 UTC
Updated at2022-09-10 10:10:23 UTC
NP-MRD IDNP0298731
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-(10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl)-2-hydroxy-2-methylpropyl acetate
Description1-(10,11-Dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl)-2-hydroxy-2-methylpropyl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 1-(10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl)-2-hydroxy-2-methylpropyl acetate is found in Actaea simplex. 1-(10,11-Dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl)-2-hydroxy-2-methylpropyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
1-(10,11-Dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0,.0,.0,.0,]docosan-8-yl)-2-hydroxy-2-methylpropyl acetic acidGenerator
1-(10,11-Dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl)-2-hydroxy-2-methylpropyl acetic acidGenerator
Chemical FormulaC38H62O12
Average Mass710.9020 Da
Monoisotopic Mass710.42413 Da
IUPAC Name1-(10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl)-2-hydroxy-2-methylpropyl acetate
Traditional Name1-(10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl)-2-hydroxy-2-methylpropyl acetate
CAS Registry NumberNot Available
SMILES
CC1CC(OC2(O)C(O)C3(C)C4CCC5C6(CC46CCC3(C)C12)CCC(OC1OC(CO)C(O)C(O)C1O)C5(C)C)C(OC(C)=O)C(C)(C)O
InChI Identifier
InChI=1S/C38H62O12/c1-18-15-20(29(33(5,6)45)47-19(2)40)50-38(46)28(18)34(7)13-14-37-17-36(37)12-11-24(49-30-27(43)26(42)25(41)21(16-39)48-30)32(3,4)22(36)9-10-23(37)35(34,8)31(38)44/h18,20-31,39,41-46H,9-17H2,1-8H3
InChI KeyDKNSWSKRPAEDMY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actaea simplexLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative Parents
Substituents
  • Cucurbitacin glycoside skeleton
  • Triterpene saponin
  • Triterpene glycoside
  • Cycloartanol-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Triterpenoid
  • Cycloartane-skeleton
  • 16-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • 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
logP1.99ALOGPS
logP1.63ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity178.12 m³·mol⁻¹ChemAxon
Polarizability79.29 ųChemAxon
Number of Rings7ChemAxon
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 Compound85229121
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]