Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:52 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036635
Secondary Accession Numbers
  • HMDB36635
Metabolite Identification
Common NameHydroxytanshinone
DescriptionHydroxytanshinone belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Hydroxytanshinone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862900
Synonyms
ValueSource
1-Hydroxy-14,16-epoxy-20-nor-5(10),6,8,13,15-abietapentaene-11,12-dioneHMDB
Chemical FormulaC19H18O4
Average Molecular Weight310.3438
Monoisotopic Molecular Weight310.120509064
IUPAC Name3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione
Traditional Name3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione
CAS Registry Number18887-18-8
SMILES
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C
InChI Identifier
InChI=1S/C19H18O4/c1-9-8-23-18-10-4-5-11-15(12(20)6-7-19(11,2)3)14(10)17(22)16(21)13(9)18/h4-5,8,12,20H,6-7H2,1-3H3
InChI KeyUPCWCCRFMPIOAP-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 Point187 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP3.14ALOGPS
logP3.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.51 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.6 m³·mol⁻¹ChemAxon
Polarizability33.47 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]+172.20131661259
DarkChem[M-H]-170.10531661259
DeepCCS[M+H]+173.13230932474
DeepCCS[M-H]-170.77430932474
DeepCCS[M-2H]-204.73830932474
DeepCCS[M+Na]+179.96630932474
AllCCS[M+H]+172.532859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+175.632859911
AllCCS[M+Na]+176.532859911
AllCCS[M-H]-180.632859911
AllCCS[M+Na-2H]-180.132859911
AllCCS[M+HCOO]-179.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydroxytanshinoneCC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C3696.5Standard polar33892256
HydroxytanshinoneCC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C2667.6Standard non polar33892256
HydroxytanshinoneCC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C2944.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxytanshinone,1TMS,isomer #1CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O[Si](C)(C)C)CCC2(C)C2842.6Semi standard non polar33892256
Hydroxytanshinone,1TBDMS,isomer #1CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O[Si](C)(C)C(C)(C)C)CCC2(C)C3063.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxytanshinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0190000000-303b948cd84ab5b3c3c82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxytanshinone GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-4039000000-f23fce8c9e528aaac1422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxytanshinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxytanshinone 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 - Hydroxytanshinone 10V, Positive-QTOFsplash10-01ox-0095000000-1459090115953e2d8ada2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Positive-QTOFsplash10-0006-1091000000-9b160e8f70ba1ebd0e8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Positive-QTOFsplash10-0v4l-4290000000-673a83937492b73d2faf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Negative-QTOFsplash10-0a4i-0029000000-857494f71efc4fd3d0672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Negative-QTOFsplash10-0a4i-0069000000-e26deb1c0ad2f400236e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Negative-QTOFsplash10-004j-0190000000-fc4e16c2c20e31bada312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Negative-QTOFsplash10-0a4i-0029000000-fac4878c9215b2cd31612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Negative-QTOFsplash10-0a4l-0069000000-4fb07203823f1c3c868f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Negative-QTOFsplash10-004l-0191000000-b9d77947a2efacfb43032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Positive-QTOFsplash10-03di-0049000000-095cdc9f44d9d61d29062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Positive-QTOFsplash10-040r-0091000000-91de6cd8c46488f5e66a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Positive-QTOFsplash10-0ue9-0090000000-cd483d43e8533af44a902021-09-22Wishart 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 IDFDB015555
KNApSAcK IDNot Available
Chemspider ID4476947
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318349
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.