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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:48:30 UTC
Update Date2022-03-07 02:54:15 UTC
HMDB IDHMDB0034876
Secondary Accession Numbers
  • HMDB34876
Metabolite Identification
Common NameCastaneiolide
DescriptionCastaneiolide, also known as fema 3879, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review very few articles have been published on Castaneiolide.
Structure
Thumb
Synonyms
ValueSource
Methylthiomethyl butyric acidHMDB
(Methylthio)methyl butyrateHMDB
FEMA 3879HMDB
Methyl 2-methylthiobutyrateHMDB
Chemical FormulaC22H28O8
Average Molecular Weight420.4529
Monoisotopic Molecular Weight420.178417872
IUPAC Name10-butyl-9,10-dihydroxy-2-pentyl-6,14-dioxatricyclo[10.3.0.0⁴,⁸]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone
Traditional Name10-butyl-9,10-dihydroxy-2-pentyl-6,14-dioxatricyclo[10.3.0.0⁴,⁸]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone
CAS Registry Number125300-50-7
SMILES
CCCCCC1CC2=C(C(O)C(O)(CCCC)CC3=C1C(=O)OC3=O)C(=O)OC2=O
InChI Identifier
InChI=1S/C22H28O8/c1-3-5-7-8-12-10-13-16(21(27)29-18(13)24)17(23)22(28,9-6-4-2)11-14-15(12)20(26)30-19(14)25/h12,17,23,28H,3-11H2,1-2H3
InChI KeyRKHYCZRKSYBVGA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • 2-furanone
  • Carboxylic acid anhydride
  • Dihydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point162 - 163 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.29ALOGPS
logP3.67ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.42 m³·mol⁻¹ChemAxon
Polarizability42.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.91931661259
DarkChem[M-H]-196.90331661259
DeepCCS[M+H]+204.65330932474
DeepCCS[M-H]-202.06830932474
DeepCCS[M-2H]-237.05330932474
DeepCCS[M+Na]+213.21930932474
AllCCS[M+H]+200.732859911
AllCCS[M+H-H2O]+198.332859911
AllCCS[M+NH4]+202.932859911
AllCCS[M+Na]+203.632859911
AllCCS[M-H]-204.132859911
AllCCS[M+Na-2H]-205.032859911
AllCCS[M+HCOO]-206.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CastaneiolideCCCCCC1CC2=C(C(O)C(O)(CCCC)CC3=C1C(=O)OC3=O)C(=O)OC2=O5420.2Standard polar33892256
CastaneiolideCCCCCC1CC2=C(C(O)C(O)(CCCC)CC3=C1C(=O)OC3=O)C(=O)OC2=O3177.8Standard non polar33892256
CastaneiolideCCCCCC1CC2=C(C(O)C(O)(CCCC)CC3=C1C(=O)OC3=O)C(=O)OC2=O3325.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Castaneiolide,1TMS,isomer #1CCCCCC1CC2=C(C(=O)OC2=O)C(O[Si](C)(C)C)C(O)(CCCC)CC2=C1C(=O)OC2=O3398.2Semi standard non polar33892256
Castaneiolide,1TMS,isomer #2CCCCCC1CC2=C(C(=O)OC2=O)C(O)C(CCCC)(O[Si](C)(C)C)CC2=C1C(=O)OC2=O3427.7Semi standard non polar33892256
Castaneiolide,2TMS,isomer #1CCCCCC1CC2=C(C(=O)OC2=O)C(O[Si](C)(C)C)C(CCCC)(O[Si](C)(C)C)CC2=C1C(=O)OC2=O3399.8Semi standard non polar33892256
Castaneiolide,1TBDMS,isomer #1CCCCCC1CC2=C(C(=O)OC2=O)C(O[Si](C)(C)C(C)(C)C)C(O)(CCCC)CC2=C1C(=O)OC2=O3630.1Semi standard non polar33892256
Castaneiolide,1TBDMS,isomer #2CCCCCC1CC2=C(C(=O)OC2=O)C(O)C(CCCC)(O[Si](C)(C)C(C)(C)C)CC2=C1C(=O)OC2=O3658.1Semi standard non polar33892256
Castaneiolide,2TBDMS,isomer #1CCCCCC1CC2=C(C(=O)OC2=O)C(O[Si](C)(C)C(C)(C)C)C(CCCC)(O[Si](C)(C)C(C)(C)C)CC2=C1C(=O)OC2=O3886.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Castaneiolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-3019100000-66395ab05842e3db1c822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Castaneiolide GC-MS (2 TMS) - 70eV, Positivesplash10-05i9-7000690000-187da829ed5405586d422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Castaneiolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Castaneiolide 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 - Castaneiolide 10V, Positive-QTOFsplash10-00fr-0009800000-b42a5a42b765fe1ac2e82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 20V, Positive-QTOFsplash10-0uml-2009300000-b41480b1e8fc1db1709e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 40V, Positive-QTOFsplash10-002f-9015000000-2ad03422f9f9477abe892016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 10V, Negative-QTOFsplash10-016r-0009800000-69a7936559e23573ec282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 20V, Negative-QTOFsplash10-004i-0009100000-bf9d87e1f65c6c03478e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 40V, Negative-QTOFsplash10-05mt-4197000000-f38d35ee1c33a54e9f782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 10V, Negative-QTOFsplash10-014i-0000900000-44e8ac582194effa71ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 20V, Negative-QTOFsplash10-014i-0000900000-265c100c9c6f50887d742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 40V, Negative-QTOFsplash10-00r2-0009100000-99cdd41cdedd91b577d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 10V, Positive-QTOFsplash10-00di-0000900000-29326f49a066222f87752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 20V, Positive-QTOFsplash10-0fk9-0002900000-6fbb7c1895162ae0bf432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Castaneiolide 40V, Positive-QTOFsplash10-00mk-1009100000-72c82675a3d0aee4682d2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB013451
KNApSAcK IDC00054136
Chemspider ID325115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound366241
PDB IDNot Available
ChEBI ID175360
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .