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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:43 UTC
Update Date2022-03-07 02:52:40 UTC
HMDB IDHMDB0030734
Secondary Accession Numbers
  • HMDB30734
Metabolite Identification
Common NameIsomorellic acid
DescriptionButyl hexanoate, also known as butyl caproate or fema 2201, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Butyl hexanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862029
Synonyms
ValueSource
Butyl hexanoic acidGenerator
Butyl caproateHMDB
Butyl caprylateHMDB
Butyl ester OF hexanoic acidHMDB
FEMA 2201HMDB
Hexanoic acid, butyl esterHMDB
N-Butyl caproateHMDB
N-Butyl hexanoateHMDB
N-Butyl N-hexanoateHMDB
N-Caproic acid N-butyl esterHMDB
(2Z)-4-[12-Hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoateGenerator
Morellic acidMeSH
IsomorellateGenerator
Chemical FormulaC33H36O8
Average Molecular Weight560.6341
Monoisotopic Molecular Weight560.241018128
IUPAC Name(2Z)-4-[12-hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid
Traditional Name(2Z)-4-[12-hydroxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=C2OC34C5CC(C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)C4(C\C=C(\C)C(O)=O)OC5(C)C
InChI Identifier
InChI=1S/C33H36O8/c1-16(2)8-9-20-26-19(11-12-30(4,5)39-26)24(34)23-25(35)21-14-18-15-22-31(6,7)41-32(28(18)36,13-10-17(3)29(37)38)33(21,22)40-27(20)23/h8,10-12,14,18,22,34H,9,13,15H2,1-7H3,(H,37,38)/b17-10-
InChI KeyCOVMVPHACFXMAX-YVLHZVERSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP4.62ALOGPS
logP6.05ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity155.44 m³·mol⁻¹ChemAxon
Polarizability59.78 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+228.86931661259
DarkChem[M-H]-217.67631661259
DeepCCS[M-2H]-267.26330932474
DeepCCS[M+Na]+241.46230932474
AllCCS[M+H]+228.932859911
AllCCS[M+H-H2O]+227.432859911
AllCCS[M+NH4]+230.332859911
AllCCS[M+Na]+230.732859911
AllCCS[M-H]-238.232859911
AllCCS[M+Na-2H]-240.232859911
AllCCS[M+HCOO]-242.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isomorellic acidCC(C)=CCC1=C2OC34C5CC(C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)C4(C\C=C(\C)C(O)=O)OC5(C)C5749.7Standard polar33892256
Isomorellic acidCC(C)=CCC1=C2OC34C5CC(C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)C4(C\C=C(\C)C(O)=O)OC5(C)C3835.8Standard non polar33892256
Isomorellic acidCC(C)=CCC1=C2OC34C5CC(C=C3C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C(=O)C4(C\C=C(\C)C(O)=O)OC5(C)C3949.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isomorellic acid,1TMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C2=C(O[Si](C)(C)C)C2=C1OC(C)(C)C=C24032.8Semi standard non polar33892256
Isomorellic acid,1TMS,isomer #2CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C2=C(O)C2=C1OC(C)(C)C=C23966.0Semi standard non polar33892256
Isomorellic acid,1TMS,isomer #3CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C2=C(O)C2=C1OC(C)(C)C=C23919.6Semi standard non polar33892256
Isomorellic acid,2TMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C2=C(O[Si](C)(C)C)C2=C1OC(C)(C)C=C23922.7Semi standard non polar33892256
Isomorellic acid,2TMS,isomer #2CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C2=C(O[Si](C)(C)C)C2=C1OC(C)(C)C=C23870.9Semi standard non polar33892256
Isomorellic acid,2TMS,isomer #3CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C2=C(O)C2=C1OC(C)(C)C=C23820.1Semi standard non polar33892256
Isomorellic acid,3TMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C2=C(O[Si](C)(C)C)C2=C1OC(C)(C)C=C23784.7Semi standard non polar33892256
Isomorellic acid,3TMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C2=C(O[Si](C)(C)C)C2=C1OC(C)(C)C=C23821.2Standard non polar33892256
Isomorellic acid,1TBDMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C)(C)C=C24275.5Semi standard non polar33892256
Isomorellic acid,1TBDMS,isomer #2CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C2=C(O)C2=C1OC(C)(C)C=C24212.6Semi standard non polar33892256
Isomorellic acid,1TBDMS,isomer #3CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C2=C(O)C2=C1OC(C)(C)C=C24158.9Semi standard non polar33892256
Isomorellic acid,2TBDMS,isomer #1CC(C)=CCC1=C2OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C)(C)C=C24359.9Semi standard non polar33892256
Isomorellic acid,2TBDMS,isomer #2CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C)(C)C=C24324.1Semi standard non polar33892256
Isomorellic acid,2TBDMS,isomer #3CC(C)=CCC1=C2OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)OC(C)(C)C4C5)C(=O)C2=C(O)C2=C1OC(C)(C)C=C24262.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3000190000-5ccd58feb8356dce55772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (1 TMS) - 70eV, Positivesplash10-014i-4100039000-4e27ff9691f49b43df0c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS ("Isomorellic acid,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomorellic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 10V, Positive-QTOFsplash10-03xu-0010190000-e6580faa402eb6f281a02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 20V, Positive-QTOFsplash10-014r-5020890000-b0762af03545984977bf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 40V, Positive-QTOFsplash10-0ap0-3090500000-a91493ab4b07196653762016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 10V, Negative-QTOFsplash10-0a4i-0010190000-f1a314f26866136b62502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 20V, Negative-QTOFsplash10-0aor-1032290000-90525eaf06c7235ee2762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 40V, Negative-QTOFsplash10-05g3-2691120000-1ca2694685abe5c7ebcb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 10V, Positive-QTOFsplash10-03di-0000090000-e1ff69a699d97b46410f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 20V, Positive-QTOFsplash10-08fu-0000290000-1763d257815dd698f7c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 40V, Positive-QTOFsplash10-0f6x-6000980000-f0ed7b52eb2fd654f7e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 10V, Negative-QTOFsplash10-0a4i-0000090000-47ed5b46695395a54cfb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 20V, Negative-QTOFsplash10-0a4i-0000190000-2a63176a1c63f8d1ed282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomorellic acid 40V, Negative-QTOFsplash10-05mo-3080930000-c3e5e4499c90419fed9b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB019923
KNApSAcK IDNot Available
Chemspider ID11791
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12294
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .