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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:23 UTC
Update Date2021-09-14 15:45:36 UTC
HMDB IDHMDB0013899
Secondary Accession Numbers
  • HMDB13899
Metabolite Identification
Common Name3-Hydroxyvalproic acid
Description3-Hydroxyvalproic acid, also known as 3-OH-vpa, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a small amount of articles have been published on 3-Hydroxyvalproic acid.
Structure
Data?1582753152
Synonyms
ValueSource
2-N-Propyl-3-hydroxypentanoic acidKegg
3-OH-VPAKegg
2-N-Propyl-3-hydroxypentanoateGenerator
3-HydroxyvalproateGenerator
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name3-hydroxy-2-propylpentanoic acid
Traditional Name3-OH-vpa
CAS Registry Number58888-84-9
SMILES
CCCC(C(O)CC)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-3-5-6(8(10)11)7(9)4-2/h6-7,9H,3-5H2,1-2H3,(H,10,11)
InChI KeyLLPFTSMZBSRZDV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
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 Solubility45.1 g/LALOGPS
logP1.31ALOGPS
logP1.57ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability17.78 ųChemAxon
Number of Rings0ChemAxon
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]+136.87231661259
DarkChem[M-H]-133.43731661259
DeepCCS[M+H]+133.18830932474
DeepCCS[M-H]-129.72330932474
DeepCCS[M-2H]-166.74830932474
DeepCCS[M+Na]+141.90930932474
AllCCS[M+H]+140.132859911
AllCCS[M+H-H2O]+136.132859911
AllCCS[M+NH4]+143.832859911
AllCCS[M+Na]+144.932859911
AllCCS[M-H]-137.232859911
AllCCS[M+Na-2H]-139.232859911
AllCCS[M+HCOO]-141.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyvalproic acidCCCC(C(O)CC)C(O)=O2533.0Standard polar33892256
3-Hydroxyvalproic acidCCCC(C(O)CC)C(O)=O1230.8Standard non polar33892256
3-Hydroxyvalproic acidCCCC(C(O)CC)C(O)=O1257.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyvalproic acid,1TMS,isomer #1CCCC(C(=O)O)C(CC)O[Si](C)(C)C1328.4Semi standard non polar33892256
3-Hydroxyvalproic acid,1TMS,isomer #2CCCC(C(=O)O[Si](C)(C)C)C(O)CC1291.6Semi standard non polar33892256
3-Hydroxyvalproic acid,2TMS,isomer #1CCCC(C(=O)O[Si](C)(C)C)C(CC)O[Si](C)(C)C1393.0Semi standard non polar33892256
3-Hydroxyvalproic acid,1TBDMS,isomer #1CCCC(C(=O)O)C(CC)O[Si](C)(C)C(C)(C)C1554.2Semi standard non polar33892256
3-Hydroxyvalproic acid,1TBDMS,isomer #2CCCC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CC1524.7Semi standard non polar33892256
3-Hydroxyvalproic acid,2TBDMS,isomer #1CCCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C1823.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9300000000-3990ddba1acdf7a6ad1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyvalproic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00a9-9560000000-d6ceafa5a0f572d012b52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyvalproic 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-Hydroxyvalproic acid 10V, Positive-QTOFsplash10-01ox-2900000000-94e5d9864b33bb6046fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Positive-QTOFsplash10-0006-9800000000-4653a737f38226b0e1262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Positive-QTOFsplash10-052g-9100000000-54e8d3c3fae9945687a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Negative-QTOFsplash10-0a4i-1900000000-a312fdd4abbafc7f9dce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Negative-QTOFsplash10-0pvj-8900000000-878d16b210cbde172bbe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Negative-QTOFsplash10-0a4i-9100000000-fe03ae181ae0356789e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Positive-QTOFsplash10-0671-9300000000-de8af454bf411a77bea12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Positive-QTOFsplash10-0006-9200000000-2e73bb8b169767753a392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-9d61a7f4f577b8d4eaeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Negative-QTOFsplash10-0a4i-9100000000-7642c8447cf6a0c49dfb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Negative-QTOFsplash10-0a4i-9000000000-34d624720a40b145201b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Negative-QTOFsplash10-053r-9000000000-9a90335f600169bbe6ab2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID118522
KEGG Compound IDC16651
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134459
PDB IDNot Available
ChEBI ID80637
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. 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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.