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Record Information
Version2.0
Created at2022-09-06 22:22:40 UTC
Updated at2022-09-06 22:22:40 UTC
NP-MRD IDNP0238895
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,4s,5r,9s,10r,13r)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
Description(1S,4S,5R,9S,10R,13R)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-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,5r,9s,10r,13r)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid is found in Smallanthus sonchifolius. Based on a literature review very few articles have been published on (1S,4S,5R,9S,10R,13R)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(1S,4S,5R,9S,10R,13R)-5-(Hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylateGenerator
Chemical FormulaC20H30O3
Average Mass318.4570 Da
Monoisotopic Mass318.21949 Da
IUPAC Name(1S,4S,5R,9S,10R,13R)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
Traditional Name(1S,4S,5R,9S,10R,13R)-5-(hydroxymethyl)-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@@]12CCC[C@](CO)([C@H]1CC[C@@]13C[C@@H](CC[C@@H]21)C(=C)C3)C(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-13-10-19-9-6-16-18(2,15(19)5-4-14(13)11-19)7-3-8-20(16,12-21)17(22)23/h14-16,21H,1,3-12H2,2H3,(H,22,23)/t14-,15+,16+,18+,19-,20+/m1/s1
InChI KeyDQKIEUZHDCNMOJ-RBLKCTMESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Smallanthus sonchifoliusLOTUS 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
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP3.53ChemAxon
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.14 m³·mol⁻¹ChemAxon
Polarizability36.34 ųChemAxon
Number of Rings4ChemAxon
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 Compound162895688
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]