(-)-Kaur-16-en-19-oic acid (CHEM025929)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:41:09 UTC
Update Date2016-11-09 01:18:10 UTC
Accession NumberCHEM025929
Identification
Common Name(-)-Kaur-16-en-19-oic acid
ClassSmall Molecule
DescriptionAn ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Kaur-16-en-19-Oic acidChEBI
(5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oic acidChEBI
ent-Kaur-16(17)-en-19-Oic acidChEBI
ent-Kaurenoic acidChEBI
Kaur-16-en-18-Oic acidChEBI
Kauren-19-Oic acidChEBI
Kaurenic acidChEBI
Kaurenoic acidChEBI
ent-Kaur-16-en-19-OateKegg
(-)-Kaur-16-en-19-OateGenerator
(5b,8a,9b,10a,13a)-Kaur-16-en-18-OateGenerator
(5b,8a,9b,10a,13a)-Kaur-16-en-18-Oic acidGenerator
(5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-OateGenerator
(5Β,8α,9β,10α,13α)-kaur-16-en-18-OateGenerator
(5Β,8α,9β,10α,13α)-kaur-16-en-18-Oic acidGenerator
ent-Kaur-16(17)-en-19-OateGenerator
ent-KaurenoateGenerator
Kaur-16-en-18-OateGenerator
Kauren-19-OateGenerator
KaurenateGenerator
KaurenoateGenerator
ent-Kaur-16-en-18-Oic acidMeSH
3beta-Hydroxy-kaurenoic acidMeSH
ent-Kaur-16-en-19-Oic acidKEGG
Chemical FormulaC20H30O2
Average Molecular Mass302.458 g/mol
Monoisotopic Mass302.225 g/mol
CAS Registry NumberNot Available
IUPAC Name(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
Traditional Name(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
SMILES[H][C@@]12C[C@]3(CC1=C)CC[C@]1([H])[C@@](C)(CCC[C@@]1(C)[C@]3([H])CC2)C(O)=O
InChI IdentifierInChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1
InChI KeyNIKHGUQULKYIGE-OTCXFQBHSA-N
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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP4.13ALOGPS
logP4.81ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.36 m³·mol⁻¹ChemAxon
Polarizability35.32 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0189000000-e32ee1de5a9c608c2a44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0391000000-e394ed814c12150daac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4980000000-a62048379e0c65cfa374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-7e4d4b429d5eff18ab7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0094000000-8f1bdf9553eed92d0c8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-1090000000-0d495a6257dc2d019e9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0089000000-c65698a8dba37e012d50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmr-0943000000-2ffd59d91ab4e2b79ac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9720000000-930c6014a094be91c659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-16d58525184e918518faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-16d58525184e918518faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-0097000000-208d1681517a7ae9b6f9Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0302664
FooDB IDFDB005672
Phenol Explorer IDNot Available
KNApSAcK IDC00000881
BiGG IDNot Available
BioCyc IDCPD1F-132
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21258059
ChEBI ID15417
PubChem Compound IDNot Available
Kegg Compound IDC11874
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20013639
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20496227
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20552528
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21823454
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21884778
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22832886
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23314342