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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:45 UTC
Update Date2022-03-07 02:53:04 UTC
HMDB IDHMDB0031672
Secondary Accession Numbers
  • HMDB31672
Metabolite Identification
Common NameArmillaribin
DescriptionArmillaribin belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Based on a literature review a small amount of articles have been published on Armillaribin.
Structure
Data?1563862155
Synonyms
ValueSource
3-Formyl-6,6,7b-trimethyl-1H,2H,4H,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoic acidHMDB
Chemical FormulaC24H30O5
Average Molecular Weight398.492
Monoisotopic Molecular Weight398.20932407
IUPAC Name3-formyl-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate
Traditional Name3-formyl-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate
CAS Registry Number119516-61-9
SMILES
COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(C)=C1
InChI Identifier
InChI=1S/C24H30O5/c1-13-6-16(28-5)8-18(26)20(13)22(27)29-19-11-24(4)17-10-23(2,3)9-14(17)7-15(12-25)21(19)24/h6,8,12,14,17,19,26H,7,9-11H2,1-5H3
InChI KeyHWLRIFRIRNSGBG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentMelleolides and analogues
Alternative Parents
Substituents
  • Melleolide-skeleton
  • O-hydroxybenzoic acid ester
  • P-methoxybenzoic acid or derivatives
  • Benzoate ester
  • Methoxyphenol
  • Salicylic acid or derivatives
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Anisole
  • M-cresol
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Toluene
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Aldehyde
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.043 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0045 g/LALOGPS
logP3.93ALOGPS
logP5.06ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.04 m³·mol⁻¹ChemAxon
Polarizability44.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.63631661259
DarkChem[M-H]-194.03131661259
DeepCCS[M-2H]-233.87130932474
DeepCCS[M+Na]+209.09930932474
AllCCS[M+H]+198.932859911
AllCCS[M+H-H2O]+196.632859911
AllCCS[M+NH4]+201.032859911
AllCCS[M+Na]+201.632859911
AllCCS[M-H]-201.232859911
AllCCS[M+Na-2H]-201.432859911
AllCCS[M+HCOO]-201.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArmillaribinCOC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(C)=C13969.5Standard polar33892256
ArmillaribinCOC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(C)=C12909.5Standard non polar33892256
ArmillaribinCOC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(C)=C12990.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Armillaribin,1TMS,isomer #1COC1=CC(C)=C(C(=O)OC2CC3(C)C2=C(C=O)CC2CC(C)(C)CC23)C(O[Si](C)(C)C)=C13186.1Semi standard non polar33892256
Armillaribin,1TBDMS,isomer #1COC1=CC(C)=C(C(=O)OC2CC3(C)C2=C(C=O)CC2CC(C)(C)CC23)C(O[Si](C)(C)C(C)(C)C)=C13402.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Armillaribin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014v-1933000000-5ecc192a37f3289d2b3e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Armillaribin GC-MS (1 TMS) - 70eV, Positivesplash10-052u-3970500000-69ed04fa169d45a0337b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Armillaribin 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 - Armillaribin 10V, Positive-QTOFsplash10-00kb-0339000000-0ac094bc56f789b392a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 20V, Positive-QTOFsplash10-014i-1943000000-9dcadafadfc2d858e0832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 40V, Positive-QTOFsplash10-014i-2910000000-adef2712af0603a8456a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 10V, Negative-QTOFsplash10-0002-0229000000-d5501dd3c19dc17f15942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 20V, Negative-QTOFsplash10-0012-0938000000-4f468823706ebcb7e9e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 40V, Negative-QTOFsplash10-053i-2930000000-3db5706133388a7d59c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 10V, Positive-QTOFsplash10-014j-0297000000-4f0cc92f2612065694bb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 20V, Positive-QTOFsplash10-00kk-3469000000-1fdb0cbc6d59db5c41fb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 40V, Positive-QTOFsplash10-02ti-1911000000-13b9f09e7e7dd041ba9f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 10V, Negative-QTOFsplash10-000t-0409000000-142023ba025694a25b5e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 20V, Negative-QTOFsplash10-000i-0938000000-a00018bca414ff3634922021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaribin 40V, Negative-QTOFsplash10-0ued-6797000000-70132769f76b5357459c2021-09-25Wishart 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 IDFDB008332
KNApSAcK IDC00055506
Chemspider ID35013377
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751179
PDB IDNot Available
ChEBI ID175182
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1827381
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.