Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:55 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036636
Secondary Accession Numbers
  • HMDB36636
Metabolite Identification
Common NameMethuyl tanshinonate
DescriptionMethuyl tanshinonate belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Methuyl tanshinonate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862901
Synonyms
ValueSource
Methuyl tanshinonic acidGenerator
Methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylic acidGenerator
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Namemethyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate
Traditional Namemethyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate
CAS Registry Number18887-19-9
SMILES
COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C
InChI Identifier
InChI=1S/C20H18O5/c1-10-9-25-18-12-6-7-13-11(15(12)17(22)16(21)14(10)18)5-4-8-20(13,2)19(23)24-3/h6-7,9H,4-5,8H2,1-3H3
InChI KeyYFDKIHAZVQFLRC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTanshinones, isotanshinones, and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 - 176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.46ALOGPS
logP3.87ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.58 m³·mol⁻¹ChemAxon
Polarizability35.99 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]+180.42231661259
DarkChem[M-H]-179.56631661259
DeepCCS[M+H]+177.14530932474
DeepCCS[M-H]-174.78730932474
DeepCCS[M-2H]-209.11130932474
DeepCCS[M+Na]+185.40230932474
AllCCS[M+H]+179.332859911
AllCCS[M+H-H2O]+176.232859911
AllCCS[M+NH4]+182.232859911
AllCCS[M+Na]+183.032859911
AllCCS[M-H]-186.132859911
AllCCS[M+Na-2H]-185.832859911
AllCCS[M+HCOO]-185.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methuyl tanshinonateCOC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C3968.6Standard polar33892256
Methuyl tanshinonateCOC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C2640.9Standard non polar33892256
Methuyl tanshinonateCOC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C2975.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methuyl tanshinonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0094000000-5575ab9274450376cbd62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methuyl tanshinonate 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 - Methuyl tanshinonate 10V, Positive-QTOFsplash10-000i-0009000000-518cc91621784f3cdb122015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Positive-QTOFsplash10-052r-1059000000-7c9442b1ed33fd9543952015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Positive-QTOFsplash10-0udu-3090000000-346e4ab8d2f49e0504212015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Negative-QTOFsplash10-000i-0009000000-2ef93dc4b089f05b0b352015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Negative-QTOFsplash10-000i-0009000000-2d1be7ca5864d2f860e12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Negative-QTOFsplash10-056r-1093000000-661d8a816955f77859f42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Positive-QTOFsplash10-004r-0097000000-605adc09a24abf1219302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Positive-QTOFsplash10-004i-0091000000-8bda5ca2a8f714a607b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Positive-QTOFsplash10-0w59-0191000000-63c66a1ca329da85a8982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Negative-QTOFsplash10-002r-0079000000-3e370463dd1c6dd3b2292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Negative-QTOFsplash10-004i-0090000000-99a1efa42b4c4ca3538d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Negative-QTOFsplash10-01ti-0091000000-2b5195239d42c60767502021-09-24Wishart 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 IDFDB015556
KNApSAcK IDNot Available
Chemspider ID542418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound624381
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.