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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:24 UTC

Update Date

2023-02-21 17:18:06 UTC

HMDB ID

HMDB0013902

Secondary Accession Numbers

HMDB13902

Metabolite Identification

Common Name

2-ene-Valproic acid

Description

2-ene-Valproic acid, also known as 2-en-valproate or 2-ene-vpa, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a small amount of articles have been published on 2-ene-Valproic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-En-valproic acid	Kegg
2-Ene-vpa	Kegg
2-En-valproate	Generator
2-Ene-valproate	Generator
2-N-Propylpent-2-enoic acid	HMDB
2-Propyl-2-pentenoic acid, (Z)-isomer	HMDB
trans-2-En-valproate	HMDB
(e)-2-Ene valproic acid	HMDB
2-EnVPA	HMDB
2-Propyl-2-pentenoic acid, sodium salt	HMDB
trans-2-En-vpa	HMDB
2-Envalproic acid	HMDB
2-Propyl-2-pentenoic acid, (e)-isomer	HMDB
e-delta(2)-Valproic acid	HMDB
trans-2-Ene-valproic acid	HMDB
2-Propyl-2-pentenoic acid	HMDB
delta2,3 VPE	HMDB
delta2-Valproic acid	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

(2E)-2-propylpent-2-enoic acid

Traditional Name

2-Ene-VPA

CAS Registry Number

Not Available

SMILES

CCC\C(=C/CC)C(O)=O

InChI Identifier

InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h5H,3-4,6H2,1-2H3,(H,9,10)/b7-5+

InChI Key

ZKNJEOBYOLUGKJ-FNORWQNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl-branched fatty acid (CHEBI:80639 )
Branched fatty acids (C16653 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013902)
Kidney (HMDB: HMDB0013902)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

Not Available

Physical Properties

State

Solid

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	3.53 g/L	ALOGPS
logP	2.31	ALOGPS
logP	2.65	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	5.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.12 m³·mol⁻¹	ChemAxon
Polarizability	16.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.831	31661259
DarkChem	[M-H]-	131.066	31661259
DeepCCS	[M+H]+	132.797	30932474
DeepCCS	[M-H]-	129.304	30932474
DeepCCS	[M-2H]-	166.327	30932474
DeepCCS	[M+Na]+	141.446	30932474
AllCCS	[M+H]+	135.5	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.4	32859911
AllCCS	[M+Na]+	140.5	32859911
AllCCS	[M-H]-	134.3	32859911
AllCCS	[M+Na-2H]-	136.6	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-ene-Valproic acid	CCC\C(=C/CC)C(O)=O	2000.9	Standard polar	33892256
2-ene-Valproic acid	CCC\C(=C/CC)C(O)=O	1112.2	Standard non polar	33892256
2-ene-Valproic acid	CCC\C(=C/CC)C(O)=O	1132.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-ene-Valproic acid,1TMS,isomer #1	CC/C=C(\CCC)C(=O)O[Si](C)(C)C	1247.4	Semi standard non polar	33892256
2-ene-Valproic acid,1TBDMS,isomer #1	CC/C=C(\CCC)C(=O)O[Si](C)(C)C(C)(C)C	1458.7	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 - 2-ene-Valproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9200000000-a3278b5bf0d6e0fb2aa3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-ene-Valproic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0092-9300000000-1b6a0cb7096c729d39f3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-ene-Valproic 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 - 2-ene-Valproic acid 10V, Positive-QTOF	splash10-0006-4900000000-d831a51244cd5b58277f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 20V, Positive-QTOF	splash10-0007-9300000000-10dbc97051aad7222497	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 40V, Positive-QTOF	splash10-0006-9000000000-0d4ff8d45f8d64e7012e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 10V, Negative-QTOF	splash10-0006-4900000000-f0260b142073e6345442	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 20V, Negative-QTOF	splash10-0005-9400000000-1d545ce3461541df4e62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 40V, Negative-QTOF	splash10-0007-9100000000-845358af30059248a3c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 10V, Negative-QTOF	splash10-0007-7900000000-d747945d70947cdad9d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 20V, Negative-QTOF	splash10-0002-9000000000-8777bb7eb09d8e1597a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 40V, Negative-QTOF	splash10-014l-9000000000-1c14aca48644f90f0819	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 10V, Positive-QTOF	splash10-002e-9300000000-0ec77478bf8e77abea14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 20V, Positive-QTOF	splash10-0a5d-9000000000-dd611f5286d4c4c448e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-ene-Valproic acid 40V, Positive-QTOF	splash10-0a5c-9000000000-990136fda80af6a050f7	2021-09-22	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

4941657

KEGG Compound ID

C16653

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437068

PDB ID

Not Available

ChEBI ID

288752

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 2-ene-Valproic acid (HMDB0013902)

MOL for HMDB0013902 (2-ene-Valproic acid)

3D MOL for HMDB0013902 (2-ene-Valproic acid)

3D SDF for HMDB0013902 (2-ene-Valproic acid)

3D-SDF for HMDB0013902 (2-ene-Valproic acid)

PDB for HMDB0013902 (2-ene-Valproic acid)

3D PDB for HMDB0013902 (2-ene-Valproic acid)

SMILES for HMDB0013902 (2-ene-Valproic acid)

INCHI for HMDB0013902 (2-ene-Valproic acid)

Structure for HMDB0013902 (2-ene-Valproic acid)

3D Structure for HMDB0013902 (2-ene-Valproic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra