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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:56:06 UTC
Update Date2022-03-07 02:55:03 UTC
HMDB IDHMDB0036761
Secondary Accession Numbers
  • HMDB36761
Metabolite Identification
Common Name7,18-Dihydroxykaurenolide
Description7,18-Dihydroxykaurenolide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 7,18-Dihydroxykaurenolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862922
Synonyms
ValueSource
7beta,18-DihydroxykaurenolideHMDB
ent-7a,18-Dihydroxy-16-kauren-19,6b-olideHMDB
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name9-hydroxy-13-(hydroxymethyl)-1-methyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one
Traditional Name9-hydroxy-13-(hydroxymethyl)-1-methyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one
CAS Registry Number7758-47-6
SMILES
CC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C3
InChI Identifier
InChI=1S/C20H28O4/c1-11-8-20-9-12(11)4-5-13(20)18(2)6-3-7-19(10-21)15(18)14(16(20)22)24-17(19)23/h12-16,21-22H,1,3-10H2,2H3
InChI KeyRDUNXXWNAKBVER-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.83ALOGPS
logP1.96ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.67ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.45 m³·mol⁻¹ChemAxon
Polarizability36.19 ųChemAxon
Number of Rings5ChemAxon
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]+177.0931661259
DarkChem[M-H]-172.36631661259
DeepCCS[M-2H]-211.77830932474
DeepCCS[M+Na]+187.00630932474
AllCCS[M+H]+181.832859911
AllCCS[M+H-H2O]+179.032859911
AllCCS[M+NH4]+184.432859911
AllCCS[M+Na]+185.132859911
AllCCS[M-H]-185.432859911
AllCCS[M+Na-2H]-185.332859911
AllCCS[M+HCOO]-185.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7,18-DihydroxykaurenolideCC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C32915.6Standard polar33892256
7,18-DihydroxykaurenolideCC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C32825.3Standard non polar33892256
7,18-DihydroxykaurenolideCC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C32963.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7,18-Dihydroxykaurenolide,1TMS,isomer #1C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C)C(=O)OC(C21)C3O2743.2Semi standard non polar33892256
7,18-Dihydroxykaurenolide,1TMS,isomer #2C=C1CC23CC1CCC2C1(C)CCCC2(CO)C(=O)OC(C21)C3O[Si](C)(C)C2732.7Semi standard non polar33892256
7,18-Dihydroxykaurenolide,2TMS,isomer #1C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C)C(=O)OC(C21)C3O[Si](C)(C)C2758.2Semi standard non polar33892256
7,18-Dihydroxykaurenolide,1TBDMS,isomer #1C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C21)C3O3036.1Semi standard non polar33892256
7,18-Dihydroxykaurenolide,1TBDMS,isomer #2C=C1CC23CC1CCC2C1(C)CCCC2(CO)C(=O)OC(C21)C3O[Si](C)(C)C(C)(C)C2981.0Semi standard non polar33892256
7,18-Dihydroxykaurenolide,2TBDMS,isomer #1C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C21)C3O[Si](C)(C)C(C)(C)C3267.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7,18-Dihydroxykaurenolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0935000000-f317179e4544589bd7e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7,18-Dihydroxykaurenolide GC-MS (2 TMS) - 70eV, Positivesplash10-0229-4361900000-5c2f58bef333616e61522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7,18-Dihydroxykaurenolide 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 - 7,18-Dihydroxykaurenolide 10V, Positive-QTOFsplash10-0159-0019000000-59fd99e9649356b71cac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Positive-QTOFsplash10-014i-0459000000-f608335d3702dae32ab82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Positive-QTOFsplash10-014l-4891000000-aeb00047f00d90752e3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Negative-QTOFsplash10-001i-0019000000-a2625dde60e5a56cd00b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Negative-QTOFsplash10-0lzi-0089000000-20b3b32ca85b67014f362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Negative-QTOFsplash10-0a4r-0090000000-4757313d2f4d8b8f4fa32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Negative-QTOFsplash10-001i-0009000000-bd69facddc36af19b9082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Negative-QTOFsplash10-001i-0097000000-b88ace95a4232db1bf142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Negative-QTOFsplash10-001i-0097000000-a01ad5fab860f74d9b9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Positive-QTOFsplash10-001i-0009000000-e2fa0bbe5e36e88183dd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Positive-QTOFsplash10-001r-0039000000-9ea056e515814b5b09212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Positive-QTOFsplash10-007n-0948000000-90d1d790c06bfb351def2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB015702
KNApSAcK IDC00007333
Chemspider ID546077
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound628758
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.