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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2023-02-21 17:16:16 UTC
HMDB IDHMDB0002207
Secondary Accession Numbers
  • HMDB02207
Metabolite Identification
Common Name3-Hydroxyisoheptanoic acid
Description3-Hydroxyisoheptanoic acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 3-Hydroxyisoheptanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyisoheptanoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxyisoheptanoic acid.
Structure
Data?1676999776
Synonyms
ValueSource
3-HydroxyisoheptanoateGenerator
3-Hydroxy-5-methylhexanoateHMDB, Generator
3-Hydroxy-5-methylhexanoic acidHMDB
3-Hydroxyisoheptanoic acidMeSH
Chemical FormulaC7H14O3
Average Molecular Weight146.1843
Monoisotopic Molecular Weight146.094294314
IUPAC Name3-hydroxy-5-methylhexanoic acid
Traditional Name3-hydroxyisoheptanoic acid
CAS Registry Number40309-49-7
SMILES
CC(C)CC(O)CC(O)=O
InChI Identifier
InChI=1S/C7H14O3/c1-5(2)3-6(8)4-7(9)10/h5-6,8H,3-4H2,1-2H3,(H,9,10)
InChI KeySCAWECGFPWPHAR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility49 g/LALOGPS
logP0.92ALOGPS
logP0.87ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.14 m³·mol⁻¹ChemAxon
Polarizability15.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.86231661259
DarkChem[M-H]-128.77731661259
DeepCCS[M+H]+136.44130932474
DeepCCS[M-H]-133.43830932474
DeepCCS[M-2H]-170.01730932474
DeepCCS[M+Na]+145.25130932474
AllCCS[M+H]+135.132859911
AllCCS[M+H-H2O]+131.132859911
AllCCS[M+NH4]+138.832859911
AllCCS[M+Na]+139.932859911
AllCCS[M-H]-133.732859911
AllCCS[M+Na-2H]-136.032859911
AllCCS[M+HCOO]-138.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyisoheptanoic acidCC(C)CC(O)CC(O)=O2398.3Standard polar33892256
3-Hydroxyisoheptanoic acidCC(C)CC(O)CC(O)=O1125.7Standard non polar33892256
3-Hydroxyisoheptanoic acidCC(C)CC(O)CC(O)=O1206.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyisoheptanoic acid,1TMS,isomer #1CC(C)CC(CC(=O)O)O[Si](C)(C)C1278.5Semi standard non polar33892256
3-Hydroxyisoheptanoic acid,1TMS,isomer #2CC(C)CC(O)CC(=O)O[Si](C)(C)C1265.4Semi standard non polar33892256
3-Hydroxyisoheptanoic acid,2TMS,isomer #1CC(C)CC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1337.1Semi standard non polar33892256
3-Hydroxyisoheptanoic acid,1TBDMS,isomer #1CC(C)CC(CC(=O)O)O[Si](C)(C)C(C)(C)C1506.7Semi standard non polar33892256
3-Hydroxyisoheptanoic acid,1TBDMS,isomer #2CC(C)CC(O)CC(=O)O[Si](C)(C)C(C)(C)C1498.9Semi standard non polar33892256
3-Hydroxyisoheptanoic acid,2TBDMS,isomer #1CC(C)CC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1767.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyisoheptanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-8c7785486d2967623f7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyisoheptanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00g3-9240000000-a93110d8dcfe7473668c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyisoheptanoic 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 - 3-Hydroxyisoheptanoic acid 10V, Positive-QTOFsplash10-004i-0900000000-4f0f7b8be6306c19d2842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Positive-QTOFsplash10-06vi-8900000000-8e494c921862c1c9e4b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-0d359b94f30656d441232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Negative-QTOFsplash10-0002-1900000000-80487e4978cb411e9e902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Negative-QTOFsplash10-0pdj-7900000000-7d31155a461e6459783e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-374bd8812777a5fcac692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Positive-QTOFsplash10-015j-9200000000-9e20a8918c8904e28e632021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-bdcf82166c5593049c512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Positive-QTOFsplash10-0536-9000000000-30891312129a2bd8cddb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Negative-QTOFsplash10-0002-4900000000-4285cef758491224a36a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Negative-QTOFsplash10-0a4i-9100000000-fb5953d0f4ec22f2d5852021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-a36d488f6a6b1853e2492021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB022907
KNApSAcK IDNot Available
Chemspider ID168187
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6547
PubChem Compound193804
PDB IDNot Available
ChEBI ID165406
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAnnunziata, Rita; Cinquini, Mauro; Gilardi, Amilcare. Optically active 2-(arylsulfinylmethyl)-oxazolines, chiral enol acetate equivalents in aldol-type condensations. Synthesis (1983), (12), 1016-17.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divry P, Vianey-Liaud C, Cotte J: Routine gas chromatographic/mass spectrometric analysis of urinary organic acids. Results over a three-year period. Biomed Environ Mass Spectrom. 1987 Nov;14(11):663-8. [PubMed:2962675 ]
  2. Lehnert W: 3-Hydroxyisoheptanoic acid: a new metabolite in isovaleric acidemia. Clin Chim Acta. 1981 Jun 2;113(1):101-3. [PubMed:7237839 ]