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Record Information
Version2.0
Created at2022-09-07 13:25:18 UTC
Updated at2022-09-07 13:25:18 UTC
NP-MRD IDNP0250567
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s)-1-[(1s,4r,5r,6r,8r,10r,11r,12s,13r,16r,18s,21r)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]-2-methoxy-2-methylpropyl acetate
Description(1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl]-2-methoxy-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. (1s)-1-[(1s,4r,5r,6r,8r,10r,11r,12s,13r,16r,18s,21r)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]-2-methoxy-2-methylpropyl acetate is found in Actaea simplex and Actaea yunnanensis. Based on a literature review very few articles have been published on (1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl]-2-methoxy-2-methylpropyl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-Dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0,.0,.0,.0,]docosan-8-yl]-2-methoxy-2-methylpropyl acetic acidGenerator
Chemical FormulaC38H62O11
Average Mass694.9030 Da
Monoisotopic Mass694.42921 Da
IUPAC Name(1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan-8-yl]-2-methoxy-2-methylpropyl acetate
Traditional Name(1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan-8-yl]-2-methoxy-2-methylpropyl acetate
CAS Registry NumberNot Available
SMILES
COC(C)(C)[C@@H](OC(C)=O)[C@H]1C[C@@H](C)[C@@H]2[C@@]3(C)CC[C@@]45C[C@@]44CC[C@H](O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]4CC[C@H]5[C@]3(C)[C@@H](O)[C@]2(O)O1
InChI Identifier
InChI=1S/C38H62O11/c1-19-16-22(29(47-20(2)39)33(5,6)45-9)49-38(44)28(19)34(7)14-15-37-18-36(37)13-12-25(48-30-27(42)26(41)21(40)17-46-30)32(3,4)23(36)10-11-24(37)35(34,8)31(38)43/h19,21-31,40-44H,10-18H2,1-9H3/t19-,21-,22-,23+,24+,25+,26+,27-,28-,29+,30+,31-,34-,35-,36-,37+,38-/m1/s1
InChI KeyYEBHGSMKFNGICI-BUTDWOEESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actaea simplexLOTUS Database
Actaea yunnanensisLOTUS 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
  • Cycloartanol-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Cycloartane-skeleton
  • Triterpenoid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Hemiacetal
  • Carboxylic acid ester
  • Polyol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
logP2.91ChemAxon
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.37 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity176.91 m³·mol⁻¹ChemAxon
Polarizability77.95 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
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 Compound162915170
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]