Hmdb loader
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 IDHMDB0013900
Secondary Accession Numbers
  • HMDB13900
Metabolite Identification
Common Name4-Hydroxyvalproic acid
Description4-Hydroxyvalproic acid, also known as 4-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 4-Hydroxyvalproic acid.
Structure
Data?1582753152
Synonyms
ValueSource
2-N-Propyl-4-hydroxypentanoic acidKegg
4-OH-VPAKegg
2-N-Propyl-4-hydroxypentanoateGenerator
4-HydroxyvalproateGenerator
4-Hydroxy-valproateHMDB
4-Hydroxyvalproate, (r*,r*)-isomerHMDB
4-Hydroxyvalproate, (r*,s*)-isomerHMDB
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name4-hydroxy-2-propylpentanoic acid
Traditional Name4-OH-vpa
CAS Registry Number60113-82-8
SMILES
CCCC(CC(C)O)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-3-4-7(8(10)11)5-6(2)9/h6-7,9H,3-5H2,1-2H3,(H,10,11)
InChI KeyOASKNPCLIHUTTL-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
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Branched fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility35.4 g/LALOGPS
logP1.17ALOGPS
logP1.33ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42 m³·mol⁻¹ChemAxon
Polarizability17.75 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]+137.32831661259
DarkChem[M-H]-133.66931661259
DeepCCS[M+H]+134.7830932474
DeepCCS[M-H]-131.32930932474
DeepCCS[M-2H]-168.43930932474
DeepCCS[M+Na]+143.59430932474
AllCCS[M+H]+139.932859911
AllCCS[M+H-H2O]+136.032859911
AllCCS[M+NH4]+143.632859911
AllCCS[M+Na]+144.732859911
AllCCS[M-H]-137.532859911
AllCCS[M+Na-2H]-139.532859911
AllCCS[M+HCOO]-141.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyvalproic acidCCCC(CC(C)O)C(O)=O2598.1Standard polar33892256
4-Hydroxyvalproic acidCCCC(CC(C)O)C(O)=O1221.8Standard non polar33892256
4-Hydroxyvalproic acidCCCC(CC(C)O)C(O)=O1285.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyvalproic acid,1TMS,isomer #1CCCC(CC(C)O[Si](C)(C)C)C(=O)O1358.6Semi standard non polar33892256
4-Hydroxyvalproic acid,1TMS,isomer #2CCCC(CC(C)O)C(=O)O[Si](C)(C)C1307.2Semi standard non polar33892256
4-Hydroxyvalproic acid,2TMS,isomer #1CCCC(CC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1392.7Semi standard non polar33892256
4-Hydroxyvalproic acid,1TBDMS,isomer #1CCCC(CC(C)O[Si](C)(C)C(C)(C)C)C(=O)O1586.1Semi standard non polar33892256
4-Hydroxyvalproic acid,1TBDMS,isomer #2CCCC(CC(C)O)C(=O)O[Si](C)(C)C(C)(C)C1540.0Semi standard non polar33892256
4-Hydroxyvalproic acid,2TBDMS,isomer #1CCCC(CC(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1834.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9300000000-64b33d0b5e662e6115b32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ri-9340000000-b8830a9ab92a9f997a6f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-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 - 4-Hydroxyvalproic acid 10V, Positive-QTOFsplash10-0006-2900000000-870e6a002defe5c185cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Positive-QTOFsplash10-0007-9700000000-8224b5a3d08a3d9a3e502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Positive-QTOFsplash10-0002-9100000000-a2223e1d0d73bfc0c3e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Negative-QTOFsplash10-0a4i-1900000000-e384ad36d90cd11a22c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Negative-QTOFsplash10-066s-5900000000-a6daf0bae02a95b5ddd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Negative-QTOFsplash10-0a4j-9200000000-d281862b7dae9170a10a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Positive-QTOFsplash10-014j-8900000000-77769416f809374af2fe2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Positive-QTOFsplash10-00kf-9200000000-d93f5d0a251e4187cc552021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Positive-QTOFsplash10-0abc-9000000000-3ea0d42cebabaad676562021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Negative-QTOFsplash10-066r-0900000000-d42c0efc60e4619dcb042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Negative-QTOFsplash10-066u-9800000000-8093b2457f4c032666d62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Negative-QTOFsplash10-0006-9000000000-39b136278ff0625518f32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 ID118528
KEGG Compound IDC16649
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134467
PDB IDNot Available
ChEBI ID80635
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.