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Record Information
Version1.0
Created at2022-09-12 16:05:53 UTC
Updated at2022-09-12 16:05:53 UTC
NP-MRD IDNP0330597
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,4s,9s,10r,12r,13s,14s)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid
Description(1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid 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. (1s,4s,9s,10r,12r,13s,14s)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-13-carboxylic acid is found in Euphorbia wallichii. Based on a literature review very few articles have been published on (1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]Hexadecane-13-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(1S,4S,9S,10R,12R,13S,14S)-5,5,9-Trimethyl-6-oxopentacyclo[11.2.1.0,.0,.0,]hexadecane-13-carboxylateGenerator
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC Name(1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0^{1,10}.0^{4,9}.0^{12,14}]hexadecane-13-carboxylic acid
Traditional Name(1S,4S,9S,10R,12R,13S,14S)-5,5,9-trimethyl-6-oxopentacyclo[11.2.1.0^{1,10}.0^{4,9}.0^{12,14}]hexadecane-13-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1(C)[C@H]2CC[C@@]34C[C@H]5[C@@H](C[C@H]3[C@]2(C)CCC1=O)[C@]5(C4)C(O)=O
InChI Identifier
InChI=1S/C20H28O3/c1-17(2)13-4-7-19-9-12-11(20(12,10-19)16(22)23)8-14(19)18(13,3)6-5-15(17)21/h11-14H,4-10H2,1-3H3,(H,22,23)/t11-,12+,13-,14+,18-,19+,20+/m1/s1
InChI KeyLWVHCBVUOMLPIW-KPGMGFTBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Euphorbia wallichiiLOTUS 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
  • Atisane diterpenoid
  • Kaurane diterpenoid
  • Villanovane, atisane, trachylobane or helvifulvane diterpenoid
  • Alkaloid or derivatives
  • Cyclopropanecarboxylic acid
  • Cyclopropanecarboxylic acid or derivatives
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • 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
logP3.72ChemAxon
pKa (Strongest Acidic)4.54ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.3 m³·mol⁻¹ChemAxon
Polarizability35.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 Compound162896887
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]