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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:29:55 UTC
Update Date2022-03-07 02:55:40 UTC
HMDB IDHMDB0038219
Secondary Accession Numbers
  • HMDB38219
Metabolite Identification
Common NameRosmadial
DescriptionRosmadial belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Rosmadial is found, on average, in the highest concentration within rosemaries (Rosmarinus officinalis). Rosmadial has also been detected, but not quantified in, several different foods, such as herbs and spices, pepper (spice), star anises (Illicium verum), cumins (Cuminum cyminum), and sweet bays (Laurus nobilis). This could make rosmadial a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Rosmadial.
Structure
Data?1563863159
Synonyms
ValueSource
(-)-RosmadialHMDB
Chemical FormulaC20H24O5
Average Molecular Weight344.4016
Monoisotopic Molecular Weight344.162373878
IUPAC Name7-hydroxy-3',3'-dimethyl-2-oxo-6-(propan-2-yl)-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde
Traditional Name7-hydroxy-6-isopropyl-3',3'-dimethyl-2-oxospiro[1-benzofuran-3,1'-cyclohexane]-2',4-dicarbaldehyde
CAS Registry Number85514-31-4
SMILES
CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O2
InChI Identifier
InChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)15-17(16(13)23)25-18(24)20(15)7-5-6-19(3,4)14(20)10-22/h8-11,14,23H,5-7H2,1-4H3
InChI KeyJBWRHBJFAVSAMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Coumaran
  • Aryl-aldehyde
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen 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 Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility47.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.76ALOGPS
logP4.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability36.73 ųChemAxon
Number of Rings3ChemAxon
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]+181.12231661259
DarkChem[M-H]-179.33131661259
DeepCCS[M+H]+189.31230932474
DeepCCS[M-H]-186.95430932474
DeepCCS[M-2H]-221.07930932474
DeepCCS[M+Na]+196.30630932474
AllCCS[M+H]+180.132859911
AllCCS[M+H-H2O]+177.132859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.632859911
AllCCS[M-H]-188.532859911
AllCCS[M+Na-2H]-188.632859911
AllCCS[M+HCOO]-189.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RosmadialCC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O23628.2Standard polar33892256
RosmadialCC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O22517.8Standard non polar33892256
RosmadialCC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C=O)C(=O)O22603.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rosmadial,1TMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1C=O2732.0Semi standard non polar33892256
Rosmadial,1TMS,isomer #2CC(C)C1=CC(C=O)=C2C(=C1O)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C2682.5Semi standard non polar33892256
Rosmadial,2TMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C2674.9Semi standard non polar33892256
Rosmadial,2TMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C2721.5Standard non polar33892256
Rosmadial,1TBDMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1C=O2955.7Semi standard non polar33892256
Rosmadial,1TBDMS,isomer #2CC(C)C1=CC(C=O)=C2C(=C1O)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C2898.2Semi standard non polar33892256
Rosmadial,2TBDMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C3059.6Semi standard non polar33892256
Rosmadial,2TBDMS,isomer #1CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C21CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C3135.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rosmadial GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-0309000000-f623455987c2374d42352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rosmadial GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2319800000-5ad28cbc5884f92494d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rosmadial GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rosmadial 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 - Rosmadial 10V, Negative-QTOFsplash10-0006-0019000000-95758903e99ee99ca15a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 20V, Negative-QTOFsplash10-0006-0339000000-c956fea811809f0b70522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 40V, Negative-QTOFsplash10-03du-2932000000-ca31d768dd21e98e053b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 10V, Negative-QTOFsplash10-0006-0009000000-d8ca376d8bc744bbe3772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 20V, Negative-QTOFsplash10-00kr-0079000000-a062efcc8c2bfa4cdca32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 40V, Negative-QTOFsplash10-000f-1192000000-0b134d3261fd43b8271a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 10V, Positive-QTOFsplash10-0002-0209000000-968194b31f34fbdf2e7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 20V, Positive-QTOFsplash10-0hi2-3239000000-57a02ee126ff42746a022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 40V, Positive-QTOFsplash10-00o0-9802000000-557fab0dce37174b98092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 10V, Positive-QTOFsplash10-002b-0009000000-f24d35e11655ca15cf1c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 20V, Positive-QTOFsplash10-00kb-1049000000-433bc20527bf55bf702e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosmadial 40V, Positive-QTOFsplash10-05r1-6692000000-b44b4b653ee7412f37992021-09-23Wishart 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 ID670
FooDB IDFDB017461
KNApSAcK IDC00031190
Chemspider ID35014540
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72996596
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1082821
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .