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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:53:37 UTC
Update Date2022-03-07 02:55:02 UTC
HMDB IDHMDB0036724
Secondary Accession Numbers
  • HMDB36724
Metabolite Identification
Common Nameent-17-Hydroxy-15-kauren-19-oic acid
Descriptionent-17-Hydroxy-15-kauren-19-oic acid, also known as 17-hydroxy-(4alpha)-kaur-15-en-18-Oic 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. ent-17-Hydroxy-15-kauren-19-oic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862916
Synonyms
ValueSource
ent-17-Hydroxy-15-kauren-19-OateGenerator
17-Hydroxy-(4alpha)-kaur-15-en-18-Oic acidHMDB
17-Hydroxy-ent-kaur-15-en-19-Oic acidHMDB
14-(Hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylateGenerator
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid
Traditional Name14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid
CAS Registry Number35030-38-7
SMILES
CC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-18-7-3-8-19(2,17(22)23)15(18)6-9-20-10-13(4-5-16(18)20)14(11-20)12-21/h11,13,15-16,21H,3-10,12H2,1-2H3,(H,22,23)
InChI KeyXEQHVCXFKPCQNM-UHFFFAOYSA-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
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point193 - 194 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP3.37ALOGPS
logP3.47ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.21 m³·mol⁻¹ChemAxon
Polarizability36.49 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.26231661259
DarkChem[M-H]-170.87331661259
DeepCCS[M-2H]-210.73630932474
DeepCCS[M+Na]+186.30130932474
AllCCS[M+H]+179.332859911
AllCCS[M+H-H2O]+176.432859911
AllCCS[M+NH4]+181.932859911
AllCCS[M+Na]+182.732859911
AllCCS[M-H]-183.432859911
AllCCS[M+Na-2H]-183.732859911
AllCCS[M+HCOO]-184.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ent-17-Hydroxy-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O2772.5Standard polar33892256
ent-17-Hydroxy-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O2496.6Standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O2750.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ent-17-Hydroxy-15-kauren-19-oic acid,1TMS,isomer #1CC1(C(=O)O)CCCC2(C)C3CCC4CC3(C=C4CO[Si](C)(C)C)CCC122744.9Semi standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acid,1TMS,isomer #2CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3CCC4CC3(C=C4CO)CCC122583.6Semi standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acid,2TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3CCC4CC3(C=C4CO[Si](C)(C)C)CCC122608.2Semi standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acid,1TBDMS,isomer #1CC1(C(=O)O)CCCC2(C)C3CCC4CC3(C=C4CO[Si](C)(C)C(C)(C)C)CCC123008.2Semi standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acid,1TBDMS,isomer #2CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3CCC4CC3(C=C4CO)CCC122862.7Semi standard non polar33892256
ent-17-Hydroxy-15-kauren-19-oic acid,2TBDMS,isomer #1CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3CCC4CC3(C=C4CO[Si](C)(C)C(C)(C)C)CCC123143.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uei-0292000000-fe5d8270c02b2c560b722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0002-4044900000-df07aea863245ee828832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 10V, Positive-QTOFsplash10-0uxr-0049000000-729ed6dfec761b5141e92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 20V, Positive-QTOFsplash10-0zfr-0295000000-31ca8c8066ff0b76bee82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 40V, Positive-QTOFsplash10-0kdu-2491000000-4f05c3a07eafacae18ca2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 10V, Negative-QTOFsplash10-014i-0079000000-e4b7eea6b0f6b74509bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 20V, Negative-QTOFsplash10-06du-0092000000-0c5ac30ecd6bce5649c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 40V, Negative-QTOFsplash10-0006-0090000000-e80bfcabea8540dde5f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 10V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 20V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 40V, Negative-QTOFsplash10-014i-2069000000-8a0667330f8673d60cba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 10V, Positive-QTOFsplash10-00xr-0094000000-26ed32f303486ca01b172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 20V, Positive-QTOFsplash10-0690-0192000000-508b0e5577dd742bf85f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Hydroxy-15-kauren-19-oic acid 40V, Positive-QTOFsplash10-0a4i-3961000000-9194f2afa010b5407ed02021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015661
KNApSAcK IDNot Available
Chemspider ID26503684
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13890715
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.