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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:53:42 UTC
Update Date2022-03-07 02:55:02 UTC
HMDB IDHMDB0036725
Secondary Accession Numbers
  • HMDB36725
Metabolite Identification
Common Nameent-17-Oxo-15-kauren-19-oic acid
Descriptionent-17-Oxo-15-kauren-19-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-Oxo-15-kauren-19-oic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862916
Synonyms
ValueSource
ent-17-oxo-15-Kauren-19-OateGenerator
14-Formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylateGenerator
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name14-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid
Traditional Name14-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid
CAS Registry Number77887-58-2
SMILES
CC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O
InChI Identifier
InChI=1S/C20H28O3/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/h11-13,15-16H,3-10H2,1-2H3,(H,22,23)
InChI KeyDIURMAFIAYOVGU-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0087 g/LALOGPS
logP3.34ALOGPS
logP3.78ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.23 m³·mol⁻¹ChemAxon
Polarizability35.55 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]+173.08931661259
DarkChem[M-H]-168.01131661259
DeepCCS[M-2H]-208.11130932474
DeepCCS[M+Na]+183.67630932474
AllCCS[M+H]+178.832859911
AllCCS[M+H-H2O]+175.932859911
AllCCS[M+NH4]+181.432859911
AllCCS[M+Na]+182.232859911
AllCCS[M-H]-183.132859911
AllCCS[M+Na-2H]-183.232859911
AllCCS[M+HCOO]-183.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ent-17-Oxo-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O3763.9Standard polar33892256
ent-17-Oxo-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O2477.9Standard non polar33892256
ent-17-Oxo-15-kauren-19-oic acidCC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O2735.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ent-17-Oxo-15-kauren-19-oic acid,1TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3CCC4CC3(C=C4C=O)CCC122684.6Semi standard non polar33892256
ent-17-Oxo-15-kauren-19-oic acid,1TBDMS,isomer #1CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3CCC4CC3(C=C4C=O)CCC122958.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uei-0391000000-9f5662fe055af96d3c0e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5298000000-ed82181793c5a887758b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-17-Oxo-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-Oxo-15-kauren-19-oic acid 10V, Positive-QTOFsplash10-014i-0197000000-d7d8c1f0876a89d1fcd42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Positive-QTOFsplash10-00xs-0291000000-8a1e428e84fb7a5db71e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Positive-QTOFsplash10-0fvl-3691000000-b9dbc7d0d75f456cf8c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Negative-QTOFsplash10-014i-0049000000-525410a8e3d3ac56c2972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Negative-QTOFsplash10-00xr-0094000000-2e311ddb2e99e0b75f9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Negative-QTOFsplash10-0597-1090000000-cb22c4c564128858033e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Negative-QTOFsplash10-014i-0009000000-d337ec43015bf5d00be62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Negative-QTOFsplash10-014i-0029000000-b0acbb4d62e0cc1b7d692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Negative-QTOFsplash10-014i-2095000000-5beeae7ffd887102a8622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Positive-QTOFsplash10-00di-0092000000-efd3617b3566b35162ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Positive-QTOFsplash10-010r-0391000000-c4c88ca77bcfe07ec2b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Positive-QTOFsplash10-0ldi-2972000000-6636db821ebcfe5fb3502021-09-24Wishart 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 IDFDB015662
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73073944
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.