Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:49:34 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036661
Secondary Accession Numbers
  • HMDB36661
Metabolite Identification
Common NameIsorosmanol
DescriptionIsorosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Isorosmanol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862905
Synonyms
ValueSource
6,11,12-Trihydroxy-8,11,13-abietatrien-20,7-olideHMDB
Chemical FormulaC20H26O5
Average Molecular Weight346.4174
Monoisotopic Molecular Weight346.178023942
IUPAC Name3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one
Traditional Name3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one
CAS Registry Number93780-80-4
SMILES
CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O
InChI Identifier
InChI=1S/C20H26O5/c1-9(2)10-8-11-12(14(22)13(10)21)20-7-5-6-19(3,4)17(20)15(23)16(11)25-18(20)24/h8-9,15-17,21-23H,5-7H2,1-4H3
InChI KeyUXVPWKDITRJELA-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point227 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP3.23ALOGPS
logP3.58ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.71 m³·mol⁻¹ChemAxon
Polarizability36.71 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]+178.84231661259
DarkChem[M-H]-174.76831661259
DeepCCS[M-2H]-217.73930932474
DeepCCS[M+Na]+192.96630932474
AllCCS[M+H]+181.932859911
AllCCS[M+H-H2O]+179.132859911
AllCCS[M+NH4]+184.632859911
AllCCS[M+Na]+185.332859911
AllCCS[M-H]-189.532859911
AllCCS[M+Na-2H]-189.732859911
AllCCS[M+HCOO]-189.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsorosmanolCC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O3590.0Standard polar33892256
IsorosmanolCC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O2613.5Standard non polar33892256
IsorosmanolCC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O3001.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isorosmanol,1TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O2804.8Semi standard non polar33892256
Isorosmanol,1TMS,isomer #2CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(O)C2OC3=O2800.0Semi standard non polar33892256
Isorosmanol,1TMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O[Si](C)(C)C)C2OC3=O2751.1Semi standard non polar33892256
Isorosmanol,2TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(O)C2OC3=O2785.5Semi standard non polar33892256
Isorosmanol,2TMS,isomer #2CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(O[Si](C)(C)C)C2OC3=O2753.8Semi standard non polar33892256
Isorosmanol,2TMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(O[Si](C)(C)C)C2OC3=O2743.2Semi standard non polar33892256
Isorosmanol,3TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(O[Si](C)(C)C)C2OC3=O2749.3Semi standard non polar33892256
Isorosmanol,1TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=O3073.7Semi standard non polar33892256
Isorosmanol,1TBDMS,isomer #2CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(O)C2OC3=O3074.4Semi standard non polar33892256
Isorosmanol,1TBDMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O[Si](C)(C)C(C)(C)C)C2OC3=O3007.3Semi standard non polar33892256
Isorosmanol,2TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(O)C2OC3=O3243.6Semi standard non polar33892256
Isorosmanol,2TBDMS,isomer #2CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(O[Si](C)(C)C(C)(C)C)C2OC3=O3224.6Semi standard non polar33892256
Isorosmanol,2TBDMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(O[Si](C)(C)C(C)(C)C)C2OC3=O3247.6Semi standard non polar33892256
Isorosmanol,3TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(O[Si](C)(C)C(C)(C)C)C2OC3=O3382.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isorosmanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9017000000-c614c247f6017b46961a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorosmanol GC-MS (3 TMS) - 70eV, Positivesplash10-0uxs-3000290000-6f3cb8e0bea3c212cccc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorosmanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorosmanol 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 - Isorosmanol 10V, Positive-QTOFsplash10-0002-0009000000-bc7dd0908440bca5eeac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 20V, Positive-QTOFsplash10-002b-3049000000-24a5a2546a845a14f00d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 40V, Positive-QTOFsplash10-066r-9052000000-5a175d98bba37e03ae3b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 10V, Negative-QTOFsplash10-0002-0009000000-cf04da223dfc6e4592ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 20V, Negative-QTOFsplash10-0002-0009000000-36a13e906ce8854a9e522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 40V, Negative-QTOFsplash10-0fbi-1098000000-4c75b00635df124f44222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 10V, Negative-QTOFsplash10-0002-0009000000-832de73587d391ac42262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 20V, Negative-QTOFsplash10-0002-0009000000-e05429a1dee70f92becd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 40V, Negative-QTOFsplash10-014i-1092000000-be5341da0db412edca1c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 10V, Positive-QTOFsplash10-0002-0009000000-7f8a0a989e9d8cd917cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 20V, Positive-QTOFsplash10-0002-0009000000-5f3ecce52bbb738d546a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorosmanol 40V, Positive-QTOFsplash10-014r-5093000000-ad6e55a717870973565f2021-09-24Wishart 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 IDFDB015588
KNApSAcK IDC00037344
Chemspider ID10169083
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11996616
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. Park SY: Neuroprotective and neurotrophic effects of isorosmanol. Z Naturforsch C. 2009 May-Jun;64(5-6):395-8. [PubMed:19678545 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.