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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:16:59 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037040
Secondary Accession Numbers
  • HMDB37040
Metabolite Identification
Common NameArmillaric acid
DescriptionArmillaric acid, also known as armillarate, 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 Armillaric acid.
Structure
Data?1563862968
Synonyms
ValueSource
ArmillarateGenerator
2-(2,4-Dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]indene-3-carboxylateHMDB
Chemical FormulaC23H28O7
Average Molecular Weight416.4642
Monoisotopic Molecular Weight416.18350325
IUPAC Name2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]indene-3-carboxylic acid
Traditional Name2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]indene-3-carboxylic acid
CAS Registry Number129251-06-5
SMILES
CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O
InChI Identifier
InChI=1S/C23H28O7/c1-11-5-13(24)7-16(25)18(11)20(28)30-17-10-22(4)15-9-21(2,3)8-12(15)6-14(19(26)27)23(17,22)29/h5-7,12,15,17,24-25,29H,8-10H2,1-4H3,(H,26,27)
InChI KeyAOCKXACXCVTXBB-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
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • O-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Benzoate ester
  • Salicylic acid or derivatives
  • Benzoic acid or derivatives
  • M-cresol
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Toluene
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclobutanol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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 Solubility12.26 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP3.22ALOGPS
logP4.27ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.97 m³·mol⁻¹ChemAxon
Polarizability44.06 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]+195.44731661259
DarkChem[M-H]-190.08631661259
DeepCCS[M-2H]-225.38830932474
DeepCCS[M+Na]+200.61630932474
AllCCS[M+H]+198.432859911
AllCCS[M+H-H2O]+196.232859911
AllCCS[M+NH4]+200.432859911
AllCCS[M+Na]+201.032859911
AllCCS[M-H]-199.832859911
AllCCS[M+Na-2H]-200.232859911
AllCCS[M+HCOO]-200.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Armillaric acidCC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O4798.4Standard polar33892256
Armillaric acidCC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O3009.4Standard non polar33892256
Armillaric acidCC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O3305.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Armillaric acid,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3424.8Semi standard non polar33892256
Armillaric acid,1TMS,isomer #2CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3382.0Semi standard non polar33892256
Armillaric acid,1TMS,isomer #3CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O3304.9Semi standard non polar33892256
Armillaric acid,1TMS,isomer #4CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C3370.1Semi standard non polar33892256
Armillaric acid,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3399.8Semi standard non polar33892256
Armillaric acid,2TMS,isomer #2CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O3282.7Semi standard non polar33892256
Armillaric acid,2TMS,isomer #3CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C3356.8Semi standard non polar33892256
Armillaric acid,2TMS,isomer #4CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O3263.9Semi standard non polar33892256
Armillaric acid,2TMS,isomer #5CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C3306.8Semi standard non polar33892256
Armillaric acid,2TMS,isomer #6CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C3243.6Semi standard non polar33892256
Armillaric acid,3TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O3283.5Semi standard non polar33892256
Armillaric acid,3TMS,isomer #2CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C3337.5Semi standard non polar33892256
Armillaric acid,3TMS,isomer #3CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C3240.8Semi standard non polar33892256
Armillaric acid,3TMS,isomer #4CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C3234.0Semi standard non polar33892256
Armillaric acid,4TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C3267.7Semi standard non polar33892256
Armillaric acid,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3663.5Semi standard non polar33892256
Armillaric acid,1TBDMS,isomer #2CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3605.4Semi standard non polar33892256
Armillaric acid,1TBDMS,isomer #3CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O3525.9Semi standard non polar33892256
Armillaric acid,1TBDMS,isomer #4CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C3595.0Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O3859.0Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #2CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O3722.4Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #3CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C3831.5Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #4CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O3687.2Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #5CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C3760.8Semi standard non polar33892256
Armillaric acid,2TBDMS,isomer #6CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C3702.7Semi standard non polar33892256
Armillaric acid,3TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O3895.1Semi standard non polar33892256
Armillaric acid,3TBDMS,isomer #2CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C3992.4Semi standard non polar33892256
Armillaric acid,3TBDMS,isomer #3CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C3887.4Semi standard non polar33892256
Armillaric acid,3TBDMS,isomer #4CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C3853.6Semi standard non polar33892256
Armillaric acid,4TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C4051.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Armillaric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kms-7892000000-89bab919b2280bd8f2692017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Armillaric acid GC-MS (3 TMS) - 70eV, Positivesplash10-0006-0091000000-5146a188da3fdf8bd5a22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Armillaric acid 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 - Armillaric acid 10V, Positive-QTOFsplash10-014j-0567900000-f44950c76b357ed20bfb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 20V, Positive-QTOFsplash10-0uea-0955100000-88746aa04bec04fb68b82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 40V, Positive-QTOFsplash10-0udi-3920000000-99bdcb1f526438196fd32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 10V, Negative-QTOFsplash10-01b9-0616900000-6441e0c9c692f1c0e8d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 20V, Negative-QTOFsplash10-00xr-0956200000-66ee22457931bbbe64ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 40V, Negative-QTOFsplash10-00di-1930000000-5c63fa662b6916c8ba532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 10V, Negative-QTOFsplash10-0udi-0109000000-4582574ae4b38a5a4cd02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 20V, Negative-QTOFsplash10-00di-0965000000-5ed4c9f099ee400271602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 40V, Negative-QTOFsplash10-00di-4912000000-b3eaa0112ab9c04e35bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 10V, Positive-QTOFsplash10-00kb-0492600000-4e483b077750f45ff8bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 20V, Positive-QTOFsplash10-0uea-4954100000-d441c1375d1d170742192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Armillaric acid 40V, Positive-QTOFsplash10-0zgs-6912000000-9e8abcdf16d0c83fafc52021-09-22Wishart 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 IDFDB016022
KNApSAcK IDC00021455
Chemspider ID19343439
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53461967
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1858881
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.