Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

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

HMDB0013899

Secondary Accession Numbers

HMDB13899

Metabolite Identification

Common Name

3-Hydroxyvalproic acid

Description

3-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

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

COMPND    HMDB0013899
HETATM    1  C1  UNL     1      -3.331  -1.044  -0.057  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.873  -0.771  -0.547  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.408   0.342   0.309  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.087   0.944   0.123  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.069   2.037   1.156  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.873   2.240   1.942  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.209   2.797   1.242  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.145   0.133   0.194  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.202   1.118   0.017  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.420  -0.823  -0.926  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.765  -1.494  -0.559  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.794  -1.816  -0.666  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.213  -1.305   1.013  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.821  -0.053  -0.105  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.961  -0.501  -1.608  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.337  -1.739  -0.401  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.486  -0.036   1.381  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.242   1.122   0.269  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.034   1.557  -0.845  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.710   2.984   2.097  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.278  -0.375   1.150  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.094   1.424  -0.906  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.743  -1.625  -1.109  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.650  -0.270  -1.870  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.995  -2.318  -1.243  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.631  -1.818   0.499  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.550  -0.709  -0.550  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    8   19
CONECT    5    6    6    7
CONECT    7   20
CONECT    8    9   10   21
CONECT    9   22
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-N-Propyl-3-hydroxypentanoic acid	Kegg
3-OH-VPA	Kegg
2-N-Propyl-3-hydroxypentanoate	Generator
3-Hydroxyvalproate	Generator

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

3-hydroxy-2-propylpentanoic acid

Traditional Name

3-OH-vpa

CAS Registry Number

58888-84-9

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 Key

LLPFTSMZBSRZDV-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

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 Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy fatty acid (CHEBI:80637 )
Branched fatty acids (C16651 )

Ontology

Not Available

Liver (HMDB: HMDB0013899)
Kidney (HMDB: HMDB0013899)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013899)

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	45.1 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.57	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-2.9	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	41.76 m³·mol⁻¹	ChemAxon
Polarizability	17.78 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]+	136.872	31661259
DarkChem	[M-H]-	133.437	31661259
DeepCCS	[M+H]+	133.188	30932474
DeepCCS	[M-H]-	129.723	30932474
DeepCCS	[M-2H]-	166.748	30932474
DeepCCS	[M+Na]+	141.909	30932474
AllCCS	[M+H]+	140.1	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyvalproic acid	CCCC(C(O)CC)C(O)=O	2533.0	Standard polar	33892256
3-Hydroxyvalproic acid	CCCC(C(O)CC)C(O)=O	1230.8	Standard non polar	33892256
3-Hydroxyvalproic acid	CCCC(C(O)CC)C(O)=O	1257.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyvalproic acid,1TMS,isomer #1	CCCC(C(=O)O)C(CC)O[Si](C)(C)C	1328.4	Semi standard non polar	33892256
3-Hydroxyvalproic acid,1TMS,isomer #2	CCCC(C(=O)O[Si](C)(C)C)C(O)CC	1291.6	Semi standard non polar	33892256
3-Hydroxyvalproic acid,2TMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C)C(CC)O[Si](C)(C)C	1393.0	Semi standard non polar	33892256
3-Hydroxyvalproic acid,1TBDMS,isomer #1	CCCC(C(=O)O)C(CC)O[Si](C)(C)C(C)(C)C	1554.2	Semi standard non polar	33892256
3-Hydroxyvalproic acid,1TBDMS,isomer #2	CCCC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CC	1524.7	Semi standard non polar	33892256
3-Hydroxyvalproic acid,2TBDMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC)O[Si](C)(C)C(C)(C)C	1823.8	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 - 3-Hydroxyvalproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9300000000-3990ddba1acdf7a6ad1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyvalproic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00a9-9560000000-d6ceafa5a0f572d012b5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-Hydroxyvalproic acid 10V, Positive-QTOF	splash10-01ox-2900000000-94e5d9864b33bb6046fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Positive-QTOF	splash10-0006-9800000000-4653a737f38226b0e126	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Positive-QTOF	splash10-052g-9100000000-54e8d3c3fae9945687a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Negative-QTOF	splash10-0a4i-1900000000-a312fdd4abbafc7f9dce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Negative-QTOF	splash10-0pvj-8900000000-878d16b210cbde172bbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Negative-QTOF	splash10-0a4i-9100000000-fe03ae181ae0356789e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Positive-QTOF	splash10-0671-9300000000-de8af454bf411a77bea1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Positive-QTOF	splash10-0006-9200000000-2e73bb8b169767753a39	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-9d61a7f4f577b8d4eaeb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 10V, Negative-QTOF	splash10-0a4i-9100000000-7642c8447cf6a0c49dfb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-34d624720a40b145201b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyvalproic acid 40V, Negative-QTOF	splash10-053r-9000000000-9a90335f600169bbe6ab	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular

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

118522

KEGG Compound ID

C16651

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134459

PDB ID

Not Available

ChEBI ID

80637

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 3-Hydroxyvalproic acid (HMDB0013899)

MOL for HMDB0013899 (3-Hydroxyvalproic acid)

3D MOL for HMDB0013899 (3-Hydroxyvalproic acid)

3D SDF for HMDB0013899 (3-Hydroxyvalproic acid)

3D-SDF for HMDB0013899 (3-Hydroxyvalproic acid)

PDB for HMDB0013899 (3-Hydroxyvalproic acid)

3D PDB for HMDB0013899 (3-Hydroxyvalproic acid)

SMILES for HMDB0013899 (3-Hydroxyvalproic acid)

INCHI for HMDB0013899 (3-Hydroxyvalproic acid)

Structure for HMDB0013899 (3-Hydroxyvalproic acid)

3D Structure for HMDB0013899 (3-Hydroxyvalproic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra