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Record Information
Version2.0
Created at2022-04-29 03:15:59 UTC
Updated at2022-04-29 03:15:59 UTC
NP-MRD IDNP0082218
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Wikstroelide L
Description(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadec-3-en-17-yl acetate belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. (+)-Wikstroelide L is found in Wikstroemia retusa. Based on a literature review very few articles have been published on (1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadec-3-en-17-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-Dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0,.0,.0,.0,]nonadec-3-en-17-yl acetic acidGenerator
Chemical FormulaC36H50O10
Average Mass642.7860 Da
Monoisotopic Mass642.34040 Da
IUPAC Name(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl acetate
Traditional Name(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl acetate
CAS Registry NumberNot Available
SMILES
CCCCCCCCC\C=C/C=C/[C@]12O[C@@H]3[C@@H]4[C@@H]5O[C@]5(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]4(O1)[C@H](C)[C@@H](OC(C)=O)[C@@]3(O2)C(C)=C
InChI Identifier
InChI=1S/C36H50O10/c1-7-8-9-10-11-12-13-14-15-16-17-18-33-44-30-26-29-32(20-37,43-29)31(40)34(41)25(19-22(4)27(34)39)36(26,46-33)23(5)28(42-24(6)38)35(30,45-33)21(2)3/h15-19,23,25-26,28-31,37,40-41H,2,7-14,20H2,1,3-6H3/b16-15-,18-17+/t23-,25-,26+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1
InChI KeyADIURPPZKNTYEV-IIOYIZDOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Wikstroemia retusaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentRhamnofolane and daphnane diterpenoids
Alternative Parents
Substituents
  • Daphnane diterpenoid
  • Ortho ester
  • Dioxepane
  • Carboxylic acid orthoester
  • 1,3-dioxepane
  • Meta-dioxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Meta-dioxolane
  • Secondary alcohol
  • Orthocarboxylic acid derivative
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • 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
logP4.64ALOGPS
logP5.22ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.65ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area144.28 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity170.32 m³·mol⁻¹ChemAxon
Polarizability70.57 ųChemAxon
Number of Rings6ChemAxon
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 Compound162870651
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References