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Record Information
Version2.0
Created at2022-09-06 22:21:22 UTC
Updated at2022-09-06 22:21:22 UTC
NP-MRD IDNP0238876
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4s,9r,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,15-dione
DescriptionKaur-16-ene-3,15-dione belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1r,4s,9r,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,15-dione is found in Liochlaena subulata. (1r,4s,9r,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,15-dione was first documented in 2009 (PMID: 21583588). Based on a literature review very few articles have been published on Kaur-16-ene-3,15-dione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H28O2
Average Mass300.4420 Da
Monoisotopic Mass300.20893 Da
IUPAC Name(1R,4S,9R,10S,13R)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,15-dione
Traditional Name(1R,4S,9R,10S,13R)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,15-dione
CAS Registry NumberNot Available
SMILES
CC1(C)[C@H]2CC[C@@]34C[C@@H](CC[C@H]3[C@]2(C)CCC1=O)C(=C)C4=O
InChI Identifier
InChI=1S/C20H28O2/c1-12-13-5-6-15-19(4)9-8-16(21)18(2,3)14(19)7-10-20(15,11-13)17(12)22/h13-15H,1,5-11H2,2-4H3/t13-,14-,15+,19-,20-/m1/s1
InChI KeyNIQFGHJOHILACS-CHGCTZGBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Jungermannia subulataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP4.79ChemAxon
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.08 m³·mol⁻¹ChemAxon
Polarizability34.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 Compound102331303
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bai SP, Luo GS, Zhang XY, Liu W: An ent-kaurane diterpenoid from Isodon japonica var. glaucocalyx. Acta Crystallogr Sect E Struct Rep Online. 2009 Jul 18;65(Pt 8):o1898. doi: 10.1107/S1600536809027159. [PubMed:21583588 ]
  2. LOTUS database [Link]