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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:23 UTC

Update Date

2021-09-14 15:45:36 UTC

HMDB ID

HMDB0013900

Secondary Accession Numbers

HMDB13900

Metabolite Identification

Common Name

4-Hydroxyvalproic acid

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0013900
HETATM    1  C1  UNL     1       3.442  -0.934   0.366  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.997  -0.507   0.482  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.443  -0.099  -0.851  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.022   0.335  -0.754  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.894  -0.742  -0.243  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.353  -0.449  -0.164  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.780   0.687   0.712  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.039  -1.598   0.328  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.078   1.579   0.073  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.025   1.487   1.319  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.184   2.827  -0.561  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.867  -0.614  -0.627  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.064  -0.538   1.198  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.558  -2.047   0.370  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.434  -1.430   0.806  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.952   0.263   1.246  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.002   0.762  -1.232  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.501  -0.923  -1.572  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.329   0.580  -1.790  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.575  -1.074   0.802  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.807  -1.670  -0.895  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.752  -0.279  -1.212  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.923   0.711   0.695  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.508   1.682   0.348  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.466   0.529   1.763  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.381  -2.191   0.750  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.142   3.653   0.019  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    9   19
CONECT    5    6   20   21
CONECT    6    7    8   22
CONECT    7   23   24   25
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-N-Propyl-4-hydroxypentanoic acid	Kegg
4-OH-VPA	Kegg
2-N-Propyl-4-hydroxypentanoate	Generator
4-Hydroxyvalproate	Generator
4-Hydroxy-valproate	HMDB
4-Hydroxyvalproate, (r,r)-isomer	HMDB
4-Hydroxyvalproate, (r,s)-isomer	HMDB

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

4-hydroxy-2-propylpentanoic acid

Traditional Name

4-OH-vpa

CAS Registry Number

60113-82-8

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 Key

OASKNPCLIHUTTL-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy 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 Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy fatty acid (CHEBI:80635 )
Branched fatty acids (C16649 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013900)
Kidney (HMDB: HMDB0013900)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013900)
Membrane (HMDB: HMDB0013900)

Source

Endogenous

Endogenous (HMDB: HMDB0013900)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	35.4 g/L	ALOGPS
logP	1.17	ALOGPS
logP	1.33	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42 m³·mol⁻¹	ChemAxon
Polarizability	17.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.328	31661259
DarkChem	[M-H]-	133.669	31661259
DeepCCS	[M+H]+	134.78	30932474
DeepCCS	[M-H]-	131.329	30932474
DeepCCS	[M-2H]-	168.439	30932474
DeepCCS	[M+Na]+	143.594	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.39 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7007 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.2 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	72.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1539.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	306.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	102.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	400.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	430.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	791.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	345.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1111.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	237.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	130.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyvalproic acid	CCCC(CC(C)O)C(O)=O	2598.1	Standard polar	33892256
4-Hydroxyvalproic acid	CCCC(CC(C)O)C(O)=O	1221.8	Standard non polar	33892256
4-Hydroxyvalproic acid	CCCC(CC(C)O)C(O)=O	1285.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyvalproic acid,1TMS,isomer #1	CCCC(CC(C)O[Si](C)(C)C)C(=O)O	1358.6	Semi standard non polar	33892256
4-Hydroxyvalproic acid,1TMS,isomer #2	CCCC(CC(C)O)C(=O)O[Si](C)(C)C	1307.2	Semi standard non polar	33892256
4-Hydroxyvalproic acid,2TMS,isomer #1	CCCC(CC(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1392.7	Semi standard non polar	33892256
4-Hydroxyvalproic acid,1TBDMS,isomer #1	CCCC(CC(C)O[Si](C)(C)C(C)(C)C)C(=O)O	1586.1	Semi standard non polar	33892256
4-Hydroxyvalproic acid,1TBDMS,isomer #2	CCCC(CC(C)O)C(=O)O[Si](C)(C)C(C)(C)C	1540.0	Semi standard non polar	33892256
4-Hydroxyvalproic acid,2TBDMS,isomer #1	CCCC(CC(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1834.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9300000000-64b33d0b5e662e6115b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00ri-9340000000-b8830a9ab92a9f997a6f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Positive-QTOF	splash10-0006-2900000000-870e6a002defe5c185cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Positive-QTOF	splash10-0007-9700000000-8224b5a3d08a3d9a3e50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Positive-QTOF	splash10-0002-9100000000-a2223e1d0d73bfc0c3e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Negative-QTOF	splash10-0a4i-1900000000-e384ad36d90cd11a22c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Negative-QTOF	splash10-066s-5900000000-a6daf0bae02a95b5ddd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Negative-QTOF	splash10-0a4j-9200000000-d281862b7dae9170a10a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Positive-QTOF	splash10-014j-8900000000-77769416f809374af2fe	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Positive-QTOF	splash10-00kf-9200000000-d93f5d0a251e4187cc55	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Positive-QTOF	splash10-0abc-9000000000-3ea0d42cebabaad67656	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 10V, Negative-QTOF	splash10-066r-0900000000-d42c0efc60e4619dcb04	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 20V, Negative-QTOF	splash10-066u-9800000000-8093b2457f4c032666d6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalproic acid 40V, Negative-QTOF	splash10-0006-9000000000-39b136278ff0625518f3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Valproic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

118528

KEGG Compound ID

C16649

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134467

PDB ID

Not Available

ChEBI ID

80635

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-Hydroxyvalproic acid (HMDB0013900)

MOL for HMDB0013900 (4-Hydroxyvalproic acid)

3D MOL for HMDB0013900 (4-Hydroxyvalproic acid)

3D SDF for HMDB0013900 (4-Hydroxyvalproic acid)

3D-SDF for HMDB0013900 (4-Hydroxyvalproic acid)

PDB for HMDB0013900 (4-Hydroxyvalproic acid)

3D PDB for HMDB0013900 (4-Hydroxyvalproic acid)

SMILES for HMDB0013900 (4-Hydroxyvalproic acid)

INCHI for HMDB0013900 (4-Hydroxyvalproic acid)

Structure for HMDB0013900 (4-Hydroxyvalproic acid)

3D Structure for HMDB0013900 (4-Hydroxyvalproic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra