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Showing Compound 6alpha,7alpha,12alpha-Trihydroxykaurenoic acid (FDB015637)

Record Information
Version1.0
Creation date2010-04-08 22:11:58 UTC
Update date2019-11-26 03:11:58 UTC
Primary IDFDB015637
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6alpha,7alpha,12alpha-Trihydroxykaurenoic acid
Description(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid, also known as (ent-6α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oate, 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. Based on a literature review a significant number of articles have been published on (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid.
CAS Number90806-33-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-OateGenerator
(ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-Oic acidGenerator
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-OateGenerator
(ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-OateGenerator
(ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oic acidGenerator
2,3,12-Trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility3.49 g/LALOGPS
logP0.99ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)-0.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.76 m³·mol⁻¹ChemAxon
Polarizability37.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O5
IUPAC name2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
InChI IdentifierInChI=1S/C20H30O5/c1-10-8-20-9-11(10)12(21)7-13(20)18(2)5-4-6-19(3,17(24)25)15(18)14(22)16(20)23/h11-16,21-23H,1,4-9H2,2-3H3,(H,24,25)
InChI KeyGDUDOACZUAVXMK-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
Classification
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 alcohol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.55%; H 8.63%; O 22.83%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6alpha,7alpha,12alpha-Trihydroxykaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-3539000000-69a6004b0e95d7a7768cSpectrum
Predicted GC-MS6alpha,7alpha,12alpha-Trihydroxykaurenoic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1001169000-ab6a3b4aeae04d580374Spectrum
Predicted GC-MS6alpha,7alpha,12alpha-Trihydroxykaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019000000-f9db9a7526cb5f5096fd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-0159000000-de2a349411ad318f24f22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5294000000-8750b5aacd1fddcdf0522016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-cd4d4a13f20040b0016b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053j-0049000000-cb78c8c447f071d134952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3097000000-d6cf9a8e8011d40ce5dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-fcf5b98fd26ec15b6b622021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0029000000-10965c6d72d1642fa0f32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-1059000000-5312b617a5c9332dc98b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-da9110d5056c23c2b1332021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyr-1089000000-7de39006620ff7b695b52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-9374000000-273adce0b43d507b1e252021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36701
CRC / DFC (Dictionary of Food Compounds) IDKFJ85-I:KFJ88-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference