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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 17:18:07 UTC

HMDB ID

HMDB0013903

Secondary Accession Numbers

HMDB13903

Metabolite Identification

Common Name

(3Z)-2-Propylpent-3-enoic acid

Description

(3Z)-2-Propylpent-3-enoic acid, also known as 3-en-valproate or 3-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 significant number of articles have been published on (3Z)-2-Propylpent-3-enoic 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
3-En-valproic acid	Kegg
3-Ene-vpa	Kegg
3-En-valproate	Generator
(3Z)-2-Propylpent-3-enoate	Generator
2-N-Propyl-3-pentenoic acid	HMDB
delta(3) Valproic acid	HMDB
delta(3)-VPA	HMDB
3-Ene-valproate	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

(3Z)-2-propylpent-3-enoic acid

Traditional Name

3-Ene-VPA

CAS Registry Number

Not Available

SMILES

CCCC(\C=C/C)C(O)=O

InChI Identifier

InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,5,7H,4,6H2,1-2H3,(H,9,10)/b5-3-

InChI Key

WTMAHJABDOHPDJ-HYXAFXHYSA-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:80640 )
Branched fatty acids (C16654 )

Ontology

Physiological effect

Not Available

Disposition

Not Available

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	2.43 g/L	ALOGPS
logP	2.33	ALOGPS
logP	2.44	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.01	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	41.37 m³·mol⁻¹	ChemAxon
Polarizability	16.14 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]+	132.9	31661259
DarkChem	[M-H]-	129.973	31661259
DeepCCS	[M+H]+	133.347	30932474
DeepCCS	[M-H]-	129.848	30932474
DeepCCS	[M-2H]-	166.909	30932474
DeepCCS	[M+Na]+	142.027	30932474
AllCCS	[M+H]+	135.0	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.0	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	136.2	32859911
AllCCS	[M+HCOO]-	138.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3Z)-2-Propylpent-3-enoic acid	CCCC(\C=C/C)C(O)=O	2021.2	Standard polar	33892256
(3Z)-2-Propylpent-3-enoic acid	CCCC(\C=C/C)C(O)=O	1083.1	Standard non polar	33892256
(3Z)-2-Propylpent-3-enoic acid	CCCC(\C=C/C)C(O)=O	1109.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3Z)-2-Propylpent-3-enoic acid,1TMS,isomer #1	C/C=C\C(CCC)C(=O)O[Si](C)(C)C	1149.9	Semi standard non polar	33892256
(3Z)-2-Propylpent-3-enoic acid,1TBDMS,isomer #1	C/C=C\C(CCC)C(=O)O[Si](C)(C)C(C)(C)C	1385.0	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 - (3Z)-2-Propylpent-3-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9100000000-8b40841a909f4cb8f92c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3Z)-2-Propylpent-3-enoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0092-9200000000-59db75ca0602a9133c82	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3Z)-2-Propylpent-3-enoic 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 - (3Z)-2-Propylpent-3-enoic acid 10V, Negative-QTOF	splash10-0006-3900000000-656fd7544599f7b43af0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 20V, Negative-QTOF	splash10-0005-9500000000-72c1ad2e9d79675c6168	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 40V, Negative-QTOF	splash10-052e-9100000000-23ea83f7f006163572be	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 10V, Negative-QTOF	splash10-0006-0900000000-a6139db738181db5c161	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 20V, Negative-QTOF	splash10-0002-9000000000-ebe8fc10e332f6d6c063	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 40V, Negative-QTOF	splash10-00kf-9000000000-a596794131db99cf1e47	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 10V, Positive-QTOF	splash10-0006-3900000000-b0b343d86a92c768ba86	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 20V, Positive-QTOF	splash10-0007-9400000000-eb447949ff54441c97b6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 40V, Positive-QTOF	splash10-0006-9000000000-72244b503b9c300a68ea	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 10V, Positive-QTOF	splash10-052e-9100000000-9fc19974e04871154189	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-566496c2d9d61c9c5015	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3Z)-2-Propylpent-3-enoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-42c18c4ab66bc1734497	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

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

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

30791778

KEGG Compound ID

C16654

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24892812

PDB ID

Not Available

ChEBI ID

80640

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 (3Z)-2-Propylpent-3-enoic acid (HMDB0013903)

MOL for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

3D MOL for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

3D SDF for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

3D-SDF for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

PDB for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

3D PDB for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

SMILES for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

INCHI for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

Structure for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

3D Structure for HMDB0013903 ((3Z)-2-Propylpent-3-enoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra