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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:59:54 UTC
Update Date2022-03-07 02:56:58 UTC
HMDB IDHMDB0041330
Secondary Accession Numbers
  • HMDB41330
Metabolite Identification
Common NameTanabalin
DescriptionTanabalin belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review a significant number of articles have been published on Tanabalin.
Structure
Data?1563863651
Synonyms
ValueSource
2-{7,8-dimethyl-3-oxo-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}-1-(furan-3-yl)ethyl acetic acidHMDB
Chemical FormulaC22H28O5
Average Molecular Weight372.4547
Monoisotopic Molecular Weight372.193674006
IUPAC Name2-{7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}-1-(furan-3-yl)ethyl acetate
Traditional Name2-{7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}-1-(furan-3-yl)ethyl acetate
CAS Registry Number172548-61-7
SMILES
CC1CCC23COC(=O)C2=CCCC3C1(C)CC(OC(C)=O)C1=COC=C1
InChI Identifier
InChI=1S/C22H28O5/c1-14-7-9-22-13-26-20(24)17(22)5-4-6-19(22)21(14,3)11-18(27-15(2)23)16-8-10-25-12-16/h5,8,10,12,14,18-19H,4,6-7,9,11,13H2,1-3H3
InChI KeyDZAYTXGDCMMRGZ-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 Parents
Substituents
  • Diterpene lactone
  • Diterpenoid
  • Clerodane diterpenoid
  • Naphthofuran
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Heteroaromatic compound
  • Furan
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 - 152 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.48ALOGPS
logP3.9ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.03 m³·mol⁻¹ChemAxon
Polarizability39.41 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]+185.84331661259
DarkChem[M-H]-180.94631661259
DeepCCS[M-2H]-226.59730932474
DeepCCS[M+Na]+202.79130932474
AllCCS[M+H]+189.732859911
AllCCS[M+H-H2O]+187.032859911
AllCCS[M+NH4]+192.332859911
AllCCS[M+Na]+193.032859911
AllCCS[M-H]-195.032859911
AllCCS[M+Na-2H]-195.332859911
AllCCS[M+HCOO]-195.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TanabalinCC1CCC23COC(=O)C2=CCCC3C1(C)CC(OC(C)=O)C1=COC=C13961.1Standard polar33892256
TanabalinCC1CCC23COC(=O)C2=CCCC3C1(C)CC(OC(C)=O)C1=COC=C12759.0Standard non polar33892256
TanabalinCC1CCC23COC(=O)C2=CCCC3C1(C)CC(OC(C)=O)C1=COC=C12944.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tanabalin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9345000000-6cdeb14757cd573f24d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tanabalin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tanabalin 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 - Tanabalin 10V, Positive-QTOFsplash10-0230-0019000000-d7ef01f1df31a8f808c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 20V, Positive-QTOFsplash10-03ds-0349000000-bbc43df880c95f6516ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 40V, Positive-QTOFsplash10-00dl-1941000000-68a5744afd53f60870a92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 10V, Negative-QTOFsplash10-00fr-0009000000-8b8d434853783c0bfb632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 20V, Negative-QTOFsplash10-004i-3029000000-eb146fe591067e6ff3842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 40V, Negative-QTOFsplash10-052b-5092000000-0b5220b3c141f5f62d7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 10V, Positive-QTOFsplash10-044i-0089000000-e481da59e2a8409578bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 20V, Positive-QTOFsplash10-0300-1092000000-23de5613fa6f6e4a4c102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 40V, Positive-QTOFsplash10-00b9-7869000000-b29a3d159e97ae5047bf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 10V, Negative-QTOFsplash10-00di-2009000000-6b0383b5b3c6486b4e5b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 20V, Negative-QTOFsplash10-0a4i-9002000000-7f9972e60e472325fd1e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tanabalin 40V, Negative-QTOFsplash10-066u-9002000000-7869e95c11fa4e80b44c2021-09-24Wishart 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 IDFDB021253
KNApSAcK IDC00054227
Chemspider ID327526
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound368920
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1891461
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.